Organic Chemistry Revision Sheets

Acyl Chlorides | Nucleophilic Addition-Elimination (with alcohol)

Reaction
REACTANTS: Acyl Chloride and Alcohol
PRODUCT: Ester and HCl
REACTION TYPE: Nucleophilic Addition-Elimination, Esterification

REACTION:

Mechanism
The alcohol acts as a nucleophile due to the lone pair of electrons on the oxygen atom attack-
ing the carbon (with a partial positive charge) in the acyl chloride group. A new carbon-oxygen
bond forms between the acyl group and the alcohol. The carbon-oxygen double bond breaks
to a single bond, giving the oxygen a negative charge. The carbon-oxygen double bond re-
forms, the carbon-chlorine bond breaks and a chloride ion is removed. Chloride ion removes
H+ ion from -RCOOH+R1 group, forming RCOOR1. Addition-elimination reaction.

Notes:
• As an ester is formed, this is an example of an esterification reaction
 Organic Chemistry Revision Sheets
Acyl Chlorides | Nucleophilic Addition-Elimination (with amines)

Reaction
REACTANTS: Acyl Chloride and Amine (primary)
PRODUCT: (Secondary) Amide and Alkyl Ammonium Chloride
REACTION TYPE: Nucleophilic Addition-Elimination

REACTION:

Mechanism
The amine acts as a nucleophile due to the lone pair of electrons on the nitrogen atom attack-
ing the carbon (with a partial positive charge) in the acyl chloride. A new carbon-nitrogen bond
forms between the acyl group and the ammonia. The carbon-oxygen double bond breaks to a
single bond, giving the oxygen a negative charge. The carbon-oxygen double bond reforms,
carbon-chlorine bond breaks and a chloride ion is removed. Amine present removes H+ ion
from -RCON+HR1 group. Addition-elimination reaction.

Notes:
• Ammonia produces a primary amide and ammonium chloride salt when reacted with acyl
chlorides.
• Primary amines produce a secondary amide and an alkyl ammonium chloride salt when
reacted with acyl chlorides.
• Secondary amines produce a tertiary amide and an alkyl ammonium chloride salt when
reacted with acyl chlorides.
 Organic Chemistry Revision Sheets
Acyl Chlorides | Nucleophilic Addition-Elimination (with NH3)

Reaction
REACTANTS: Acyl Chloride and Ammonia
PRODUCT: Amide and Ammonium Chloride (salt)
REACTION TYPE: Nucleophilic Addition-Elimination

REACTION:

Mechanism
The ammonia acts as a nucleophile due to the lone pair of electrons on the nitrogen atom
attacking the carbon (with a partial positive charge) in the acyl chloride. A new carbon-nitro-
gen bond forms between the acyl group and the ammonia. The carbon-oxygen double bond
breaks to a single bond, giving the oxygen a negative charge. The carbon-oxygen double
bond reforms, the carbon-chlorine bond breaks and a chloride ion is removed. The ammonia
present removes H+ ion from -RCONH3+ group. Addition-elimination reaction.

Notes:
• Ammonia produces a primary amide and ammonium chloride salt when reacted with acyl
chlorides.
• Primary amines produce a secondary amide and an alkyl ammonium chloride salt when
reacted with acyl chlorides.
• Secondary amines produce a tertiary amide and an alkyl ammonium chloride salt when
reacted with acyl chlorides.
 Organic Chemistry Revision Sheets
Acyl Chlorides | Nucleophilic Addition-Elimination (with water)

Reaction
REACTANTS: Acyl Chloride and H2O
PRODUCT: Carboxylic Acid and HCl
REACTION TYPE: Nucleophilic Addition-Elimination, Hydrolysis of acyl chloride

REACTION:

Mechanism
H2O acts as a nucleophile due to the lone pair of electrons on the oxygen atom attacking
the carbon (with a partial positive charge) in the acyl chloride. A new carbon-oxygen bond
forms and the carbon-oxygen double bond breaks to a single bond, giving the oxygen a
negative charge. The carbon-oxygen double bond reforms, the carbon-chlorine bond breaks
and a chloride ion is removed. The chloride ion removes a H+ ion from -OH2+ group, forming
RCOOH. Addition-elimination reaction.

Notes:
• Acyl chlorides are highly reactive and the reaction is vigorous, with heat given off (exothermic)
and fumes of HCl released.
 Organic Chemistry Revision Sheets
Alcohols | Elimination to form alkene (dehydration)

Reaction
REACTANTS: Alcohol
CONDITIONS: Heat, Acid Catalyst (concentrated H2SO4 or concentrated H3PO4)
PRODUCT: Alkene
REACTION TYPE: Elimination Reaction, dehydration

REACTION:
(example of
ethanol)

Mechanism (simplified)
-OH group on alcohol accepts a H+ ion from acid*, becoming -OH2+ (alcohol is
'protonated'). The carbon-oxygen bond breaks, forming a water molecule and a positively
charged carbon atom (carbocation). A neighbouring carbon-hydrogen breaks, giving an elec-
tron pair to the carboncation, forming a carbon-carbon double bond. H+ is released. H2O is
'removed' from the alcohol - dehydration. Elimination reaction.

Notes:
• The mechanism shown is a simplification as it is highly unlikely a primary carbocation would
form (due to its instability as an intermediate).
• *It must be noted the H+ ion comes from the concentrated acid (not shown in the
mechanism), either H2SO4 or H3PO4.
• The removal of a water molecule makes this a dehydration reaction.
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with Br2)

Reaction
REACTANTS: Alkene and Bromine (Br2)
CONDITIONS: Non-polar organic solvent (or pure liquid bromine)
PRODUCT: Dibromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
Br2 acts as an electrophile so the bromine-bromine bond is polarised by the carbon-carbon
double bond so the bromine atom with a partial positive charge accepts an electron pair
from the carbon-carbon double bond. During the reaction the carbon-carbon double bond
breaks, forming a postively charged carbon (carbocation). The negatively charged bromide
ion bonds with the carbocation. Br2 is 'added' across the double carbon-carbon bond. Addi-
tion reaction.

Notes:
• The high electron density in the carbon-carbon double bond (pi-bond) polarises the
bromine molecule to create the Br δ+ electrophile.
• This reaction is often used to identify an alkene as the colour of bromine water
changes from orange / brown to colourless when mixed with an alkene (due to the
above reaction).
 Organic Chemistry Revision Sheets
Alkenes | Hydration (with H2O in presence of acid, H+)

Reaction
REACTANTS: Alkene and H2O
CONDITIONS: Acid Catalyst
PRODUCT: Alcohol
REACTION TYPE: Electrophilic Addition, Acid Catalysed Hydration

REACTION:
(example of
ethene)

Mechanism
H3O+ acts as an electrophile because one of its Hδ+ atoms accepts an electron pair from the
carbon-carbon double bond, causing H2O to form from the H3O+. The carbon-carbon double
bond breaks, forming a postively charged carbon (carbocation). The lone pair of electrons on
an oxygen atom in H2O form a bond with the carbocation. Another water molecule removes
a H+ from the -OH2+ group and H3O+ is reformed. H2O is 'added' across the carbon-carbon
double bond - hydration. Addition reaction.

Notes:
• The reaction must be carried out in acidic conditions to form a H3O+ (hydroxonium) ion.

H2O + H+ → H3O+
• If a primary or secondary carbocation can be formed during the reaction, the secondary carbocation
will form more readily than the primary carbocation - creating 'major' and 'minor' products*.
• The secondary carbocation is more stable due to an increased positive inductive effect from neigh-
bouring alkyl chains.
• *The product mixture will contain more of the major than the minor product.
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with H2SO4)

Reaction
REACTANTS: Alkene and H2SO4 (Concentrated Sulfuric Acid)
CONDITIONS: Concentrated H2SO4
PRODUCT: Alkyl Hydrogensulfate
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
H2SO4 acts as an electrophile because its hydrogen atoms have a large partial positive
charge, so one of them accepts an electron pair from the carbon-carbon double bond. Dur-
ing the reaction the carbon-carbon double bond breaks, forming a postively charged carbon
(carbocation). The negatively charged hydrogensulfate ion bonds with the carbocation. H and
HSO4 is 'added' across the carbon-carbon double bond. Addition reaction.

Notes:
• If a primary or secondary carbocation can be formed during
the reaction, the secondary carbocation will form more
readily than the primary carbocation - creating 'major' and
'minor' products*.
• The secondary carbocation is more stable due to increased positive

• Oxygen atoms in the sulfuric acid have lone pairs of electrons (not
shown in the mechanism above).
• *The product mixture will contain more of the major product than
the minor product.
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with HBr)

Reaction
REACTANTS: Alkene and HBr (Hydrogen Bromide)
PRODUCT(S): Bromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
HBr acts as an electrophile because its hydrogen atom (with a partial positive charge)
accepts an electron pair from the carbon-carbon double bond. During the reaction the
carbon-carbon double bond breaks, forming a postively charged carbon ion (carbocation).
The negatively charged bromide ion bonds with the carbocation. HBr is 'added' across the
carbon-carbon double bond. Addition reaction.

Notes:
• If a primary or secondary carbocation can be
formed during the reaction, the secondary
carbocation will form more readily than the
primary carbocation - creating 'major' and
'minor' products*.
• The secondary carbocation is more stable due
to increased positive inductive effect from neigh-
bouring alkyl chains.
• *The product mixture will contain more of the
major product than the minor product.
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Subsititution, Friedel-Crafts (Acylation)

Reaction
REACTANTS: Benzene and Acyl Chloride
CONDITIONS: Warm and AlCl3 catalyst
PRODUCT: (Aromatic) Ketone
REACTION TYPE: Electrophilic Substitution, Acylation

REACTION:
(example of
benzene)

Mechanism
Acylium (RCO+) ion acts as an electrophile due to its carbocation accepting an electron
pair from the delocalised ring of electrons in the benzene ring. A carbon-carbon bond forms.
The carbon-hydrogen bond breaks to give the electron pair back to the ring of delocalised
electrons. RCO+ ion replaces H on benzene ring. Substitution reaction.

Notes:
• Acylium (RCO+) ion is formed by reacting an acyl chloride with a halogen carrier (AlCl3)

• H+ ion removed from benzene ring combines with [AlCl4]- to reform AlCl3 catalyst and HCl is
formed:
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Subsititution, Friedel-Crafts (Alkylation)

Reaction
REACTANTS: Benzene and Halogenoalkane
CONDITIONS: Warm and AlCl3 catalyst
PRODUCT: Alkylbenzene
REACTION TYPE: Electrophilic Substitution, Alkylation

REACTION:
(example of
benzene)

Mechanism
Alkyl (R+) ion acts as an electrophile due to its carbocation accepting an electron pair
from the delocalised ring of electrons in the benzene ring. Carbon-carbon bond forms. Car-
bon-hydrogen bond breaks to give electron pair back to delocalised ring of electrons. R+ ion
replaces H on benzene ring. Substitution reaction.

Notes:
• Alkyl (R+) ion is formed by reacting a halogenoalkane with a halogen carrier (AlCl3)

• H+ ion removed from benzene ring combines with [AlCl4]- to reform AlCl3 catalyst and HCl is
formed
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Substitution (Halogenation, with Br2)

Reaction
REACTANTS: Benzene and Halogen
CONDITIONS: Halogen carrier (AlCl3, AlBr3 or Fe)
PRODUCT: Halogenated Arene (chloro-benzene, bromo-benzene)
REACTION TYPE: Electrophilic Substitution, Halogenation

REACTION:
(example of
benzene)

Mechanism
Bromine molecule acts as an electrophile because it is polarised sufficiently by a
halogen carrier (AlBr3) and accepts an electron pair from the delocalised ring of electrons
in the benzene ring. A carbon-bromine bond forms. The carbon-hydrogen bond breaks to
the give electron pair back to delocalised ring of electrons. Br replaces H on benzene ring.
Substitution reaction.

Notes:
• Benzene is unable to undergo halogenation without a halogen carrier as the delocalised elec-
tron ring is unable to polarilse the halogen moleucle enough to form an electrophile.
• The halogen carrier poalrises the halogen molecule to the point of enabling one of the halogen
atoms (now with a partial positive charge) to act as an electrophile and accept a pair of elec-
trons from benzene.
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Subsititution, (Nitration, with HNO3)

Reaction
REACTANTS: Benzene and Nitric Acid
CONDITIONS: 55oC and conc. sulfuric acid (H2SO4)
PRODUCT: Nitrobenzene
REACTION TYPE: Electrophilic Substitution, Nitration

REACTION:
(example of
benzene)

Mechanism
Nitronium (NO2+) ion acts as an electrophile due to its positively charged nitrogen atom
accepting an electron pair from the delocalised ring of electrons in the benzene ring. A Car-
bon-nitrogen bond forms. The carbon-hydrogen bond breaks to give electron pair back to
delocalised ring of electrons. NO2+ ion replaces H on benzene ring - substitution reaction.

Notes:
• Nitronium ion is formed by the reaction of concentrated nitric acid with concentrated sulfuric acid

• H+ ion removed from benzene ring combines with hydrogen sulfate (HSO4-) ion
to reform catalyst H2SO4:
H+ + HSO4- → H2SO4
 Organic Chemistry Revision Sheets
Carbonyl (C=O) Tests

Aldehydes
warm
RHO + 2Ag(NH3)2+(aq) + 3OH-(aq) 2Ag(s) + ROO- + 4NH3(aq) + 2H2O(l)
TEST: Heat with Tollens' Reagent
silver (solid)
RESULT: Silver mirror will form Aldehyde Carboxylate Ion

TEST:
warm
Heat with Fehling's solution RHO + 2Cu2+(aq) + 5OH-(aq) Cu2O(s) + ROO- + 3H2O(l)

Copper (I) Oxide (solid)

RESULT: Brick red precipitate will form
Aldehyde Carboxylate Ion

Carbonyls
TEST: Brady's Reagent (2,4-dinitrophenylhydrazine in dilute acid)

RESULT: Orange prepcipitate forms

Methyl Carbonyl
TEST: Warm solution of iodine and sodium hydroxide

RESULT: Yellow crystals form

 Organic Chemistry Revision Sheets
Carbonyl Compounds | Nucleophilic Addition (KCN, H+)

Reaction
REACTANTS: Carbonyl (aldehyde or ketone) and KCN (in acid)
PRODUCT: Hydroxynitrile
REACTION TYPE: Nucleophilic Addition

REACTION:

Mechanism
Cyanide ion (:CN-) comes from KCN(aq) and acts as a nucleophile due to its lone pair
of electrons, attacking the carbon (with partial positive charge) in the carbonyl group.
Carbon-carbon bond forms. The carbon-oxygen double bond breaks to a single bond, giving
the oxygen a negative charge. The negative oxygen is protonated in dilute acid (H2SO4), form-
ing a hydroxyl group. Hydroxynitrile is formed. CN and H are added to the carbonyl. Addition
reaction.

Notes:
• HCN is sometimes written as the reactant, but HCN is very reactive and dangerous how-
ever. By using KCN in dilute acid, the same product can be formed as with HCN.

HCN + RR'CO → RR'C(OH)CN

• If a chiral carbon centre is formed in the product, the final product mixture will be racemic
containing both enantiomers in a 50:50 ratio. This is because carbonyl groups are planar and
there is equal chance of the :CN- nucleophile attacking the carbonyl group from above or
below the plane - producing two possible enantiomers in equal amounts.
 Organic Chemistry Revision Sheets
Carbonyl Compounds | Nucleophilic Addition (NaBH4)

Reaction
REACTANTS: Carbonyl (aldehyde or ketone) and NaBH4 or LiAlH4
PRODUCT: Alcohol
REACTION TYPE: Nucleophilic Addition, reduction

REACTION:
(example of
ketone)

Mechanism
Hydride ion (:H-) comes from reducing agent (NaBH4 or LiAlH4*) and acts as a nucleophile
due to its lone pair of electrons attacking the carbon (with partial positive charge) in the
carbonyl group. A carbon-hydrogen bond forms. The carbon-oxygen double bond breaks
to a single bond, giving the oxygen a negative charge. The negative oxygen is protonated by
water, forming a hydroxyl group and a hydroxide ion. Alcohol is formed, H is added to the
carbonyl.Addition reaction.

Notes:
• Aldehydes form primary alcohols when reduced.
• Ketones form secondary alcohols when reduced.
• *NaBH4 and LiAlH4 are reducing agents, they are able to provide hydride (:H-) ions that are
needed for the reduction of carbonyls.
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with Br2)

Reaction
REACTANTS: Alkene and Bromine (Br2)
CONDITIONS: Non-polar organic solvent (or pure liquid bromine)
PRODUCT: Dibromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
Br2 acts as an electrophile so the bromine-bromine bond is polarised by the carbon-carbon
double bond so the bromine atom with a partial positive charge accepts an electron pair
from the carbon-carbon double bond. During the reaction the carbon-carbon double bond
breaks, forming a postively charged carbon (carbocation). The negatively charged bromide
ion bonds with the carbocation. Br2 is 'added' across the double carbon-carbon bond. Addi-
tion reaction.

Notes:
• The high electron density in the carbon-carbon double bond (pi-bond) polarises the
bromine molecule to create the Br δ+ electrophile.
• This reaction is often used to identify an alkene as the colour of bromine water
changes from orange / brown to colourless when mixed with an alkene (due to the
above reaction).
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with HBr)

Reaction
REACTANTS: Alkene and HBr (Hydrogen Bromide)
PRODUCT(S): Bromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
HBr acts as an electrophile because its hydrogen atom (with a partial positive charge)
accepts an electron pair from the carbon-carbon double bond. During the reaction the
carbon-carbon double bond breaks, forming a postively charged carbon ion (carbocation).
The negatively charged bromide ion bonds with the carbocation. HBr is 'added' across the
carbon-carbon double bond. Addition reaction.

Notes:
• If a primary or secondary carbocation can be
formed during the reaction, the secondary
carbocation will form more readily than the
primary carbocation - creating 'major' and
'minor' products*.
• The secondary carbocation is more stable due
to increased positive inductive effect from neigh-
bouring alkyl chains.
• *The product mixture will contain more of the
major product than the minor product.
 Organic Chemistry Revision Sheets
Carbonyl Compounds | Nucleophilic Addition (KCN, H+)

Reaction
REACTANTS: Carbonyl (aldehyde or ketone) and KCN (in acid)
PRODUCT: Hydroxynitrile
REACTION TYPE: Nucleophilic Addition

REACTION:

Mechanism
Cyanide ion (:CN-) comes from KCN(aq) and acts as a nucleophile due to its lone pair
of electrons, attacking the carbon (with partial positive charge) in the carbonyl group.
Carbon-carbon bond forms. The carbon-oxygen double bond breaks to a single bond, giving
the oxygen a negative charge. The negative oxygen is protonated in dilute acid (H2SO4), form-
ing a hydroxyl group. Hydroxynitrile is formed. CN and H are added to the carbonyl. Addition
reaction.

Notes:
• HCN is sometimes written as the reactant, but HCN is very reactive and dangerous how-
ever. By using KCN in dilute acid, the same product can be formed as with HCN.

HCN + RR'CO → RR'C(OH)CN

• If a chiral carbon centre is formed in the product, the final product mixture will be racemic
containing both enantiomers in a 50:50 ratio. This is because carbonyl groups are planar and
there is equal chance of the :CN- nucleophile attacking the carbonyl group from above or
below the plane - producing two possible enantiomers in equal amounts.
 Organic Chemistry Revision Sheets
Alkanes | Free Radical Substitution

Reaction
REACTANTS: Alkane and Halogen
CONDITIONS: U.V (ultraviolet) light
PRODUCT(S): Halogenoalkane and Hydrogen Halide
REACTION TYPE: Free Radical Substitution

REACTION:
(example of
methane and
chlorine)

Mechanism
INITIATION STEP: Halogen molecule undergoes heterolytic fission to form radical species:

PROPAGATION STEP: Radical species reacts with alkane to form alkyl radical and HCl.
Alkyl radical then reacts with halogen molecule, reforming another halogen radical, creating
a chain reaction:

TERMINATION STEP: Radical species combine to end chain reaction:

Notes:
• Heterolytic fission is the even breaking of a covalent bond (each bonded atom gets an electron and
becomes a radical species).
• UV light provides the energy required for hetereolytic fission.
• Further substitution reactions can occur, eventually forming tetrachloromethane:
chloromethane to dichloromethane to trichloromethane to tetrachloromethane
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (SN1)

Reaction
REACTANTS: Halogenoalkane and Nucleophile
REACTION TYPE: Nucleophilic Substitution, SN1

REACTION:
(example of
2-bromo-2-meth-
ylpropane)

Mechanism
The first step of the SN1 mechanism is the breaking of the carbon-halogen bond in the
halogenoalkane, forming a carbocation. The nucleophile is then able to form a bond with
the carbocation.

Notes:
• The SN1 reaction occurs (usually) with tertiary halogenoalkanes and only slightly with second-
ary halogenoalkanes. This is because the carbon-halogen bond is too 'crowded' by alkyl groups for
the nucleophile to attack the partially positive carbon directly.
• SN1 reaction is slower than SN2 reaction.
• SN2 reaction occurs mainly with primary halogenoalkanes (and, to a lesser extent, secondary halog-
enoalkanes).
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (SN2)

Reaction
REACTANTS: Halogenoalkane and Nucleophile
REACTION TYPE: Nucleophilic Substitution, SN2

REACTION:
(example of
bromoethane)

Mechanism
SN2 reaction mechanisms have only one step. The nucleophile attacks the carbon-halogen
bond directly, forming a new carbon-nucleophile bond as the carbon-halogen bond breaks.

Notes:
• The SN2 reaction occurs (usually) with primary halogenoalkanes and only slightly with sec-
ondary halogenoalkanes. This is because the carbon-halogen bond in the primary halogenoalkane is
more available for the nucleophile to attack than the partially positive carbon directly.
• SN2 reaction is faster than SN1 reaction.
• SN1 reaction occurs mainly with tertiary halogenoalkanes (and, to a lesser extent, secondary halog-
enoalkanes).
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with Br2)

Reaction
REACTANTS: Alkene and Bromine (Br2)
CONDITIONS: Non-polar organic solvent (or pure liquid bromine)
PRODUCT: Dibromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
Br2 acts as an electrophile so the bromine-bromine bond is polarised by the carbon-carbon
double bond so the bromine atom with a partial positive charge accepts an electron pair
from the carbon-carbon double bond. During the reaction the carbon-carbon double bond
breaks, forming a postively charged carbon (carbocation). The negatively charged bromide
ion bonds with the carbocation. Br2 is 'added' across the double carbon-carbon bond. Addi-
tion reaction.

Notes:
• The high electron density in the carbon-carbon double bond (pi-bond) polarises the
bromine molecule to create the Br δ+ electrophile.
• This reaction is often used to identify an alkene as the colour of bromine water
changes from orange / brown to colourless when mixed with an alkene (due to the
above reaction).
 Organic Chemistry Revision Sheets
Alkenes | Electrophilic Addition (with HBr)

Reaction
REACTANTS: Alkene and HBr (Hydrogen Bromide)
PRODUCT(S): Bromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

Mechanism
HBr acts as an electrophile because its hydrogen atom (with a partial positive charge)
accepts an electron pair from the carbon-carbon double bond. During the reaction the
carbon-carbon double bond breaks, forming a postively charged carbon ion (carbocation).
The negatively charged bromide ion bonds with the carbocation. HBr is 'added' across the
carbon-carbon double bond. Addition reaction.

Notes:
• If a primary or secondary carbocation can be
formed during the reaction, the secondary
carbocation will form more readily than the
primary carbocation - creating 'major' and
'minor' products*.
• The secondary carbocation is more stable due
to increased positive inductive effect from neigh-
bouring alkyl chains.
• *The product mixture will contain more of the
major product than the minor product.
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Subsititution, Friedel-Crafts (Acylation)

Reaction
REACTANTS: Benzene and Acyl Chloride
CONDITIONS: Warm and AlCl3 catalyst
PRODUCT: (Aromatic) Ketone
REACTION TYPE: Electrophilic Substitution, Acylation

REACTION:
(example of
benzene)

Mechanism
Acylium (RCO+) ion acts as an electrophile due to its carbocation accepting an electron
pair from the delocalised ring of electrons in the benzene ring. A carbon-carbon bond forms.
The carbon-hydrogen bond breaks to give the electron pair back to the ring of delocalised
electrons. RCO+ ion replaces H on benzene ring. Substitution reaction.

Notes:
• Acylium (RCO+) ion is formed by reacting an acyl chloride with a halogen carrier (AlCl3)

• H+ ion removed from benzene ring combines with [AlCl4]- to reform AlCl3 catalyst and HCl is
formed:
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Subsititution, Friedel-Crafts (Alkylation)

Reaction
REACTANTS: Benzene and Halogenoalkane
CONDITIONS: Warm and AlCl3 catalyst
PRODUCT: Alkylbenzene
REACTION TYPE: Electrophilic Substitution, Alkylation

REACTION:
(example of
benzene)

Mechanism
Alkyl (R+) ion acts as an electrophile due to its carbocation accepting an electron pair
from the delocalised ring of electrons in the benzene ring. Carbon-carbon bond forms. Car-
bon-hydrogen bond breaks to give electron pair back to delocalised ring of electrons. R+ ion
replaces H on benzene ring. Substitution reaction.

Notes:
• Alkyl (R+) ion is formed by reacting a halogenoalkane with a halogen carrier (AlCl3)

• H+ ion removed from benzene ring combines with [AlCl4]- to reform AlCl3 catalyst and HCl is
formed
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Substitution (Halogenation, with Br2)

Reaction
REACTANTS: Benzene and Halogen
CONDITIONS: Halogen carrier (AlCl3, AlBr3 or Fe)
PRODUCT: Halogenated Arene (chloro-benzene, bromo-benzene)
REACTION TYPE: Electrophilic Substitution, Halogenation

REACTION:
(example of
benzene)

Mechanism
Bromine molecule acts as an electrophile because it is polarised sufficiently by a
halogen carrier (AlBr3) and accepts an electron pair from the delocalised ring of electrons
in the benzene ring. A carbon-bromine bond forms. The carbon-hydrogen bond breaks to
the give electron pair back to delocalised ring of electrons. Br replaces H on benzene ring.
Substitution reaction.

Notes:
• Benzene is unable to undergo halogenation without a halogen carrier as the delocalised elec-
tron ring is unable to polarilse the halogen moleucle enough to form an electrophile.
• The halogen carrier poalrises the halogen molecule to the point of enabling one of the halogen
atoms (now with a partial positive charge) to act as an electrophile and accept a pair of elec-
trons from benzene.
 Organic Chemistry Revision Sheets
Benzene | Electrophilic Subsititution, (Nitration, with HNO3)

Reaction
REACTANTS: Benzene and Nitric Acid
CONDITIONS: 55oC and conc. sulfuric acid (H2SO4)
PRODUCT: Nitrobenzene
REACTION TYPE: Electrophilic Substitution, Nitration

REACTION:
(example of
benzene)

Mechanism
Nitronium (NO2+) ion acts as an electrophile due to its positively charged nitrogen atom
accepting an electron pair from the delocalised ring of electrons in the benzene ring. A Car-
bon-nitrogen bond forms. The carbon-hydrogen bond breaks to give electron pair back to
delocalised ring of electrons. NO2+ ion replaces H on benzene ring - substitution reaction.

Notes:
• Nitronium ion is formed by the reaction of concentrated nitric acid with concentrated sulfuric acid

• H+ ion removed from benzene ring combines with hydrogen sulfate (HSO4-) ion
to reform catalyst H2SO4:
H+ + HSO4- → H2SO4
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (with NH3)

Reaction
REACTANTS: Halogenoalkane and Ammonia (NH3)
CONDITIONS: Heat*, Ethanolic conditions
PRODUCT(S): Amine and Ammonium Halide Salt
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

Mechanism
Ammonia (NH3) acts as a nucleophile, due to its lone pair of electrons on the nitrogen
atom and attacks the partially positive carbon atom in the carbon-halogen bond. The
carbon-halogen bond breaks, forming an (aliphatic) amine and ammonium halide salt. NH2
group is substituted for the halogen group.

Notes:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the nitrile.
• *A sealed container containing reactants is heated (otherwise ammonia would escape due its high
volatility).
• The amine formed in the reaction is actually a stronger base than ammonia, so an ammonium-alkyl
salt may be formed. The amine can be obtained by adding sodium hydroxide to the mixture - forcing
the amine group to 'release' a H+ ion and become a neutral molecule.
• The strength of the carbon-halogen bond (bond enthalpy) determines the speed of the reaction. The
stronger the bond, the slower the nucleophilic substitution reaction. C-F bond is strongest, giving the
slowest reaction; C-I bond is weakest, giving the fastest reaction.
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (with OH-(aq))

Reaction
REACTANTS: Halogenoalkane and Sodium Hydroxide, NaOH (for OH- ions)
CONDITIONS: Aqueous ('aq' - water present)
PRODUCT(S): Alcohol and Halide Ion (sodium halide salt if sodium hydroxide used)
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

Mechanism
Hydroxide ion (OH-) acts as a nucleophile and attacks the partially positive carbon atom in
the carbon-halogen bond. The carbon-halogen breaks, forming alcohol and halide ion. OH
group is substituted for the halogen group.

Notes:
• Reaction must be carried out in aqueous conditions (in water), otherwise an elimination
reaction will occur and an alkene will be formed.
• The strength of the carbon-halogen bond (bond enthalpy) determines the speed of the reaction. The
stronger the bond, the slower the nucleophilic substitution reaction. C-F bond is strongest, giving the
slowest reaction; C-I bond is weakest, giving the fastest reaction.
 Organic Chemistry Revision Sheets
Alkanes | Free Radical Substitution

Reaction
REACTANTS: Alkane and Halogen
CONDITIONS: U.V (ultraviolet) light
PRODUCT(S): Halogenoalkane and Hydrogen Halide
REACTION TYPE: Free Radical Substitution

REACTION:
(example of
methane and
chlorine)

Mechanism
INITIATION STEP: Halogen molecule undergoes heterolytic fission to form radical species:

PROPAGATION STEP: Radical species reacts with alkane to form alkyl radical and HCl.
Alkyl radical then reacts with halogen molecule, reforming another halogen radical, creating
a chain reaction:

TERMINATION STEP: Radical species combine to end chain reaction:

Notes:
• Heterolytic fission is the even breaking of a covalent bond (each bonded atom gets an electron and
becomes a radical species).
• UV light provides the energy required for hetereolytic fission.
• Further substitution reactions can occur, eventually forming tetrachloromethane:
chloromethane to dichloromethane to trichloromethane to tetrachloromethane
 Chemistry Revision Sheets
Equations for CIE

Moles (amounts of substance)

mass moles = g
Mass moles =
molar mass molar mass = g mol-1

concentration = mol dm-3

Solution moles = concentration x volume
volume = dm3

p = pressure (Pa) R = gas constant (8.31 J K-1 mol-1)

Gas pV = nRT
V = volume (m3) T = temperature (K)

Energy, Enthalpy and Entropy

q = energy c = specific heat capacity (J g-1 K-1)
Calorimetry q = mc∆T change (J or kJ) ∆T = temperature change (K or oC)

Bond Enthalpies ∆H = ∑(bond energies of reactants) - ∑(bond energies of products)

∆H = change in enthalpy (kJ mol-1), bond enthalpies = kJ mol-1)

moles enthalpy = kJ mol-1

Enthalpy enthalpy =
energy change (q) = kJ
energy change (q)

∆G = Gibbs Free Energy (kJ mol-1) ∆H = enthalpy change (kJ mol-1)

Gibbs Free Energy ∆G = ∆H - T∆S ∆S = entropy change (kJ K-1 mol-1) T =temperature (K)

R = gas constant (8.31 J K-1 mol-1) K = rate constant

∆G = - RT ln K
ln = natural logarithm T =temperature (K)

∆S = entropy change (J K-1 mol-1)

Entropy ∆S = ∑So(products) - ∑So(reactants) So = standard entropy (J K-1 mol-1)

Rates of Reaction
Rate = mol dm-3 s-1 , [ ] = concentration
Rate Equation rate = k x [A]x[B]y[C]z x,y,z
= orders with respect to A, B and C
 Chemistry Revision Sheets
Equations for CIE

Equilibrium
Equilibrium Constant K
[C]c[D]d For the equilibrium aA + bB ⇌ cC + dD
Kc = [ ] = concentration
c
[A]a[B]b

Equilibrium Constant K
(PC )c x (PD )d For the equilibrium aA(g) + bB(g) ⇌ cC(g) + dD(g)
Kp =
p (PA ) x (PB )
a b PX = partial pressure (Pa)

For the equilibrium AaBb(s) ⇌ aA (aq) + bB (aq)

x+ y-

Solubility Constant K x+ a
Ksp = [A ] [B ] y- b
[ ] = concentration
sp
Ksp = solubility constant

[A (organic)] For the equilibrium A(aqueous) ⇌ A(organic)

Partition Coeffcient K Kpc = [ ] = concentration
pc [A (aqueous)] Kpc = partician coefficient

[M(X)6] For the equilibrium [M(H2O)6 ]+ + 6X⇌ [M(X)6 ]++ 6H2O

Stability Constant K Kstab [ ] = concentration
stab [M(H2O)6][X]6 Kstan = stability constant

Chromatography
Distance travelled by sample R = no units
Retention Factor Rf Rf = f
solvent front = distance travelled by solvent
Solvent Front

Acids, Bases and pH

+
[H ][A ]
-
For the weak acid dissociation HA ⇌ H+ + A-
Acid Dissociation Constant K Ka =
(aq) (aq)
[ ] = concentration
a
[HA ] (aq) Ka = acid dissociation constant (mol dm-3)

pKa pKa = -log10Ka

Ionic Product of Water K +

Kw = [H ][OH ]
- Kw = ionic product of water (mol2 dm-6)
w (aq) aq)
at 298K, Kw = 1.00 x 10-14 mol2 dm-6

pH
+ + +
pH = -log10[H ] (aq)
[H ] = concentration of H
(aq) (aq)

+
[H ] = 10-pH
(aq)
+
 Chemistry Revision Sheets
Equations for CIE

Electrochemistry
Ecell = EMF (electromotive force) of electrochemical cell (V)
Electromotive Force E Ecell = Ereduction - Eoxidation Eredution = standard electrode potential of cathode
cell
Eoxidation = standard electrode potential of anode
Conditions for standard electrode potentials = 298K, 1 mol dm-3 and 100kPa

F = Faraday constant (9.65 x 104 coulombs per mole)

Faraday Constant F=Le L = Avagadros constant (6.022 x 1023)
e = charge of an electron (1.60 x 10-19 coulombs)

Q = coulombs (unit of charge)

Coulombs Q=It I = current (c s-1)
t = time (s)
E = electrode potential (v)
[oxidised species]
Nernst Equation 0
E = E + (0.059/z)log E0 = standard electrode potential (v)
z = number of electrons transferred
[reduced species]
[ ] = concentration (mol dm-3)

Electrochemistry ∆G0 = Gibbs free energy (standard) n = number of moles

∆G0 = - n Ecell
0
F
(feasibility) Ecell = cell potential (standard) F = Faraday constant

Assorted
relative formula mass of desired product
Atom Economy Atom Economy = x 100
relative formula mass of all reactants (sum of)

actual yield
Percentage Yield Percentage Yield = x 100
theoretical mass

(Isotope 1 mass x % abundance) + (Isotope 2 mass x % abundance)..

Relative Atomic Mass A Ar =
r total % abundance (100)

Dilution Vi Ci = VfCf Vi = initial volume

Ci = initial concentration
Vf = final volume (after dilution)
Cf = final concentration (after dilution)
 Chemistry Revision Sheets
Equations for Edexcel

Moles (amounts of substance)

mass moles = g
Mass moles =
molar mass molar mass = g mol-1

concentration = mol dm-3

Solution moles = concentration x volume
volume = dm3

p = pressure (Pa) R = gas constant (8.31 J K-1 mol-1)

Gas pV = nRT
V = volume (m3) T = temperature (K)

Energy, Enthalpy and Entropy

Q = energy change c = specific heat capacity (J g-1 K-1)
Calorimetry Q = mc∆T (J or kJ) ∆T = temperature change (K or oC)

Bond Enthalpies ∆H = ∑(bond energies of reactants) - ∑(bond energies of products)

∆H = change in enthalpy (kJ mol-1), bond enthalpies = kJ mol-1)

moles enthalpy = kJ mol-1

Enthalpy enthalpy =
energy change (Q) = kJ
energy change (Q)

∆G = Gibbs Free Energy (kJ mol-1) ∆H = enthalpy change (kJ mol-1)

Gibbs Free Energy ∆G = ∆H - T∆S ∆S = entropy change (kJ K-1 mol-1) T =temperature (K)

R = gas constant (8.31 J K-1 mol-1) K = rate constant

∆G = - RT ln K
ln = natural logarithm T =temperature (K)

∆S = entropy change (J K-1 mol-1)

Entropy ∆S = ∑So(products) - ∑So(reactants) So = standard entropy (J K-1 mol-1)

∆S = entropy change (J K-1 mol-1)

∆S(Total) = ∆S(System) + ∆S(Surroundings) ∆S = entropy change of reaction
System

-∆H ∆S(Surroundings) = entropy change of surroundings (kJ K-1 mol-1)

∆S(Surroundings) = ∆H = enthalpy change (kJ mol-1)
T T = temperature (K)
 Chemistry Revision Sheets
Equations for Edexcel

Equilibrium
Equilibrium Constant K
[C]c[D]d For the equilibrium aA + bB ⇌ cC + dD
Kc = [ ] = concentration
c
[A]a[B]b

Equilibrium Constant K
(PC )c x (PD )d For the equilibrium aA(g) + bB(g) ⇌ cC(g) + dD(g)
Kp =
p (PA ) x (PB )
a b PX = partial pressure (Pa)

Rates of Reaction
Rate = mol dm-3 s-1 , [ ] = concentration
Rate Equation rate = k x [A]x[B]y[C]z x,y,z
= orders with respect to A, B and C

-Ea k = rate constant Ea = activation energy (kJ mol-1)

Arrhenius Equation k = Ae RT A = constant T = temperature
e = base of natural log R = gas constant (8.31 J K-1 mol-1)

Ea
lnk = - + lnA ln = natural logarithm
RT

Acids, Bases and pH

+
[H ][A ]
-
For the weak acid dissociation HA ⇌ H+ + A-
Acid Dissociation Constant K Ka =
(aq) (aq)
[ ] = concentration
a
[HA ] (aq) Ka = acid dissociation constant (mol dm-3)

pKa pKa = -log10Ka

Ionic Product of Water K +

Kw = [H ][OH ]
- Kw = ionic product of water (mol2 dm-6)
w (aq) aq)
at 298K, Kw = 1.00 x 10-14 mol2 dm-6

pH
+ + +
pH = -log10[H ] (aq)
[H ] = concentration of H
(aq) (aq)

+
[H ] = 10-pH
(aq)
+
 Chemistry Revision Sheets
Equations for Edexcel

Electrochemistry
Ecell = EMF (electromotive force) of electrochemical cell (V)
Electromotive Force E Ecell = Ereduction - Eoxidation Eredution = standard electrode potential of cathode
cell
Eoxidation = standard electrode potential of anode
Conditions for standard electrode potentials = 298K, 1 mol dm-3 and 100kPa

Chromatography
Distance travelled by sample R = no units
Retention Factor Rf Rf = f
solvent front = distance travelled by solvent
Solvent Front

Assorted
relative formula mass of desired product
Atom Economy Atom Economy = x 100
relative formula mass of all reactants (sum of)

actual yield
Percentage Yield Percentage Yield = x 100
theoretical mass

(Isotope 1 mass x % abundance) + (Isotope 2 mass x % abundance)..

Relative Atomic Mass A Ar =
r total % abundance (100)

Dilution Vi Ci = VfCf Vi = initial volume

Ci = initial concentration
Vf = final volume (after dilution)
Cf = final concentration (after dilution)
 Organic Chemistry Revision Sheets
Functional Groups and Tests

Acid Anhydride

Acyl Chloride
TEST: SLOWLY add water
RESULT: Misty white fumes (HCl) given off

Alcohol
TEST: Warm with acidified potassium di
choromate (VI) (Cr2O72- / H+)
RESULT: Solution turns from orange to
green (for primary and secondary
alcohols only)

Aldehyde
TEST: Warm with Fehling's Solution or
Warm with Tollens' Reagent
RESULT: Fehling's - red precipitate forms
from blue solution
Tollens' - silver mirror forms
 Organic Chemistry Revision Sheets
Functional Groups and Tests

Alkene
TEST: Addition of bromine water
RESULT: Solution turns from orange-brown
to colourless

Amide

Amine

Carboxylic Acid
TEST: Add sodium carbonate (Na2CO3),
test gas formed with limewater
RESULT: Effervesence and gas turns lime-
water from colourless to cloudy
 Organic Chemistry Revision Sheets
Functional Groups and Tests

Ester
IDENTIFICATION: Sweet, fruity smell

Ether
'Dry Ether' refers to the use of di-
ethyl-ether as a solvent with no water
present

Halogenoalkane (haloalkane)
TEST: Addition of hydroxide ions (in
ethanol), followed by (dilute) nitric
acid and silver nitrate (AgNO3)
RESULT: Precipitate forms, colour is based
on halogen
Cl = white ppt, Br = cream ppt
and I = yellow ppt

Ketone
TEST: Brady's Reagent, 2,4-dinitrophe-
nylhydrazine in dilute acid.
RESULT: Orange-Yellow crystals form.
Note - this is a positive test for the C=O bond
(get same result with aldehyde)
 Organic Chemistry Revision Sheets
Functional Groups Tests

Alcohols warm
3ROH + Cr2O72-(aq) + 14H+(aq) 3RHO + 2Cr3+(aq) + 7H2O(l)
TEST: Warm with acidified potassium
dichromate (VI), Cr2O72- / H+ orange solution green solution

RESULT: Solution will change colour from

orange to green Alcohol Aldehyde or Ketone

Aldehydes warm
RHO + 2Ag(NH3)2+(aq) + 3OH-(aq) 2Ag(s) + ROO- + 4NH3(aq) + 2H2O(l)
TEST: Heat with Tollens' Reagent
silver (solid)
RESULT: Silver mirror will form Aldehyde Carboxylate Ion

warm
RHO + 2Cu2+(aq) + 5OH-(aq) Cu2O(s) + ROO- + 3H2O(l)
TEST: Heat with Fehling's solution
Copper (I) Oxide (solid)
RESULT: Brick red precipitate will form
Aldehyde Carboxylate Ion

Alkenes
CnH2n + Br2(aq) CnH2nBr2
TEST: Addition of Bromine Water

RESULT: Solution will change colour from Alkene Dibromoalkane

orange-brown to colourless

Carboxylic Acid
Addition of Sodium Carbonate RCOOH + CO32-(aq) RCOO-(aq) + CO2(g) + H2O(l)
TEST:

RESULT: Effervesence, gas produced turns lime- Carboxylic Acid Carboxylate Ion
water from colourless to cloudy

Halogenoalkane (haloalkane)
RX + OH- ROH + X-
TEST: Addition of hydroxide ions (in
ethanol), followed by (dilute)
nitric acid and silver nitrate Halogenoalkane Alcohol
(AgNO3) X-(aq) + Ag+(aq) AgX(s)

RESULT: Coloured precipitate forms AgCl(s) = white ppt, AgBr(s) = cream ppt and AgI(s) = yellow ppt
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (with :CN-)

Reaction
REACTANTS: Halogenoalkane and Sodium or Potassium Cyanide (NaCN or KCN)
CONDITIONS: Heat under reflux, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Nitrile and Halide Ion (forms salt with Na+ or K+)
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

Mechanism
Cyanide ion (CN-) acts as a nucleophile and attacks the partially positive carbon atom in
the carbon-halogen bond. The carbon-halogen breaks, forming a nitrile and a halide ion. CN
group is substituted for the halogen group.

Notes:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the nitrile.
• Reaction is heated under reflux to ensure no volatile substances are lost.
• The strength of the carbon-halogen bond (bond enthalpy) determines the speed of the reaction. The
stronger the bond, the slower the nucleophilic substitution reaction. C-F bond is strongest, giving the
slowest reaction; the C-I bond is weakest, giving the fastest reaction.
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (with NH3)

Reaction
REACTANTS: Halogenoalkane and Ammonia (NH3)
CONDITIONS: Heat*, Ethanolic conditions
PRODUCT(S): Amine and Ammonium Halide Salt
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

Mechanism
Ammonia (NH3) acts as a nucleophile, due to its lone pair of electrons on the nitrogen
atom and attacks the partially positive carbon atom in the carbon-halogen bond. The
carbon-halogen bond breaks, forming an (aliphatic) amine and ammonium halide salt. NH2
group is substituted for the halogen group.

Notes:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the amine.
• *A sealed container containing reactants is heated (otherwise ammonia would escape due its high
volatility).
• The amine formed in the reaction is actually a stronger base than ammonia, so an ammonium-alkyl
salt may be formed. The amine can be obtained by adding sodium hydroxide to the mixture - forcing
the amine group to 'release' a H+ ion and become a neutral molecule.
• The strength of the carbon-halogen bond (bond enthalpy) determines the speed of the reaction. The
stronger the bond, the slower the nucleophilic substitution reaction. C-F bond is strongest, giving the
slowest reaction; C-I bond is weakest, giving the fastest reaction.
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (with OH-(aq))

Reaction
REACTANTS: Halogenoalkane and Sodium Hydroxide, NaOH (for OH- ions)
CONDITIONS: Aqueous ('aq' - water present)
PRODUCT(S): Alcohol and Halide Ion (sodium halide salt if sodium hydroxide used)
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

Mechanism
Hydroxide ion (OH-) acts as a nucleophile and attacks the partially positive carbon atom in
the carbon-halogen bond. The carbon-halogen breaks, forming alcohol and halide ion. OH
group is substituted for the halogen group.

Notes:
• Reaction must be carried out in aqueous conditions (in water), otherwise an elimination
reaction will occur and an alkene will be formed.
• The strength of the carbon-halogen bond (bond enthalpy) determines the speed of the reaction. The
stronger the bond, the slower the nucleophilic substitution reaction. C-F bond is strongest, giving the
slowest reaction; C-I bond is weakest, giving the fastest reaction.
 Organic Chemistry Revision Sheets
Halogenoalkanes | Elimination (with OH-)

Reaction
REACTANTS: Halogenoalkane and Sodium (or Potassium) Hydroxide, NaOH
CONDITIONS: Heat under reflux, Ethanolic conditions (in ethanol, no water present)
PRODUCT(S): Alkene and Halide Ion (and water)
REACTION TYPE: Elimination

REACTION:
(example of
chloroethane)

Mechanism
Hydroxide ion (:OH-) acts as a base due to the lone pair of electrons on the oxygen atom
allowing it to remove a H+ ion from the carbon atom next to the carbon-halogen bond. The
carbon-halogen bond breaks, forming a double bond between carbon atoms. The halogen
group is eliminated from the halogenoalkane.

Notes:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the alkene.
• Unlike in nucleophilic substitution reactions of halogenoalkanes, the hydroxide ion is acting as a
base.
• The strength of the carbon-halogen bond (bond enthalpy) determines the speed of the reaction. The
stronger the bond, the slower the nucleophilic substitution reaction. C-F bond is strongest, giving
slowest reaction; C-I bond is weakest, giving fastest reaction.
 Inorganic Revision Sheet
Ion Tests for Edexcel

Flame Tests
METAL ION COLOUR

Lithium, Li+ Red

Note:
Sodium, Na + Yellow-Orange Magnesium and Beryllium
ions produce no colour in a
Potassium, K+ Lilac flame

Calcium, Ca2+ Brick Red

Strontium, Sr2+ Red

Barium, Ba2+ Pale Green

+
Ammonium, NH4
+
Test: Add sodium hydroxide and NH4 (aq) + OH-(aq) NH3(g) + H2O(l)
warm
Result: Ammonia formed (turn damp
red litmus paper blue)
Turns damp red litmus paper blue

Halide Ions, Cl-, Br- and I-

WHITE precipitate dissolves in
Cl-(aq) + Ag+(aq) AgCl(s) dilute ammonia (NH3)
Test: Add dilute nitric acid
followed by silver nitrate CREAM precipitate dissolves in
Result: Solid precipitate forms
Br-(aq) + Ag+(aq) AgBr(s) concentrated ammonia (NH3)
Precipitates have
different solubilities in I-(aq) + Ag+(aq) AgI(s) YELLOW precipitate unable
to dissolve in concentrated
ammonia (NH3)
ammonia (NH3)
 Inorganic Revision Sheet
Ion Tests for Edexcel

2-
Carbonate Ion, CO3
2-
CO3 (aq) + 2H+(aq) H2O(l) + CO2(g)
Test: Add weak acid (aq) from weak acid
Result: Effervesence (gas
produced), gas turns
limewater from colourless Turns limewater cloudy
to cloudy
(from colourless)

-
Hydrogen Carbonate Ion, HCO3
Test: Add weak acid (aq)
Result: Effervesence (gas
HCO-3 (aq) + H+(aq) H2O(l) + CO2(g)
produced), gas turns from weak acid
limewater from colourless
to cloudy
Turns limewater cloudy
(from colourless)

2-
Sulfate Ion, SO4
2-
SO4 (aq) + Ba2+(aq) BaSO4(s) WHITE precipitate
Test: Add acidified Barium
Chloride, BaCl(aq) from BaCl(aq)
Result: White precipitate forms
 Organic Chemistry Revision Sheets
Alkanes | Free Radical Substitution

Reaction
REACTANTS: Alkane and Halogen
CONDITIONS: U.V (ultraviolet) light
PRODUCT(S): Halogenoalkane and Hydrogen Halide
REACTION TYPE: Free Radical Substitution

REACTION:
(example of
methane and
chlorine)

Mechanism
INITIATION STEP: Halogen molecule undergoes heterolytic fission to form radical species:

PROPAGATION STEP: Radical species reacts with alkane to form alkyl radical and HCl.
Alkyl radical then reacts with halogen molecule, reforming another halogen radical, creating
a chain reaction:

TERMINATION STEP: Radical species combine to end chain reaction:

Notes:
• Heterolytic fission is the even breaking of a covalent bond (each bonded atom gets an electron and
becomes a radical species).
• UV light provides the energy required for hetereolytic fission.
• Further substitution reactions can occur, eventually forming tetrachloromethane:
chloromethane to dichloromethane to trichloromethane to tetrachloromethane
 Inorganic Revision Sheet
Metal Aqua Ion Reactions for CIE
Cu2+ and Co2+

NaOH(aq)
[Cu(H2O)6]2+(aq) Cu(H2O)4(OH)2(s)
Copper (II), Cu 2+
blue solution
dropwise
blue precipitate

dropwise NaOH or NH3= blue ppt

NH3(aq) NH3(aq)
excess NaOH = no change [Cu(H2O)6]2+(aq) dropwise Cu(H2O)4(OH)2(s) [Cu (NH3)4 (H2O)2]2+(aq)
excess
excess NH3 = deep blue solution
blue solution blue precipitate deep blue solution

NaOH(aq)
[Co(H2O)6]2+(aq) Co(H2O)4(OH)2(s)

Cobalt (II), Co2+

dropwise
pink solution blue precipitate

dropwise NaOH or NH3= blue ppt NH3(aq) NH3(aq)

excess NaOH = no change [Co(H2O)6]2+(aq) dropwise Co(H2O)4(OH)2(s) excess [Co(NH3)6]2+(aq)
excess NH3 = yellow solution
pink solution blue precipitate yellow solution

Ligand Exchange
[Cu(H2O)6]2+(aq) + 4Cl-(aq) [Cu(Cl)4]2-(aq) + 6H2O(l)
Copper (II), Cu2+
blue solution yellow solution

[Cu(H2O)6]2+(aq) + 4NH3(aq) [Cu(NH3)4(H2O)2]2+(aq) + 4H2O(l)

blue solution deep blue solution

[Co(H2O)6]2+(aq) + 4Cl-(aq) [Co(Cl)4]2-(aq) + 6H2O(l)

Cobalt (II), Co2+
pink solution blue solution

[Co(H2O)6]2+(aq) + 6NH3(aq) [Co(NH)6]2+(aq) + 6H2O(l)

pink solution pale yellow solution

 Inorganic Revision Sheet
Metal Aqua Ion Reactions for CIE

Redox Reactions (half equations)

Fe3+(aq) + e- Fe2+(aq)
purple solution green solution

Fe2+(aq) Fe3+(aq) + e-
green solution purple solution

MnO4-(aq) + 8H+(aq) + 5e- Mn2+(aq) + 4H2O(l)

deep purple solution pale pink solution

Cr2O72-(aq) + 14H+(aq) + 6e- 2Cr3+(aq) + 7H2O(l)

orange solution green solution

Shapes of complexes
Complex Ion Shape
[Cu(H2O)6]2+ Octahedral
Cu(H2O)4(OH)2 Octahedral
[Cu (NH3)4 (H2O)2]2+ Octahedral
[Cu(Cl)4]2- Tetrahedral
[Co(H2O)6]2+ Octahedral
Co(H2O)4(OH)2 Octahedral
[Co(Cl)4]2- Tetrahedral
 Inorganic Revision Sheet
Metal Aqua Ion Reactions for Edexcel
Fe2+, Fe3+, Cu2+, Cr3+ and Co2+
NaOH(aq) NaOH(aq)
[Fe(H2O)6]2+(aq) Fe(H2O)4(OH)2(s) No change
Iron (II), Fe 2+
green solution
dropwise
green precipitate
excess

dropwise NaOH or NH3= green ppt NH3(aq) NH3(aq)

excess NaOH = no change [Fe(H2O)6]2+(aq) dropwise Fe(H2O)4(OH)2(s) excess No change
excess NH3 = no change
green solution green precipitate

NaOH(aq) NaOH(aq)
[Fe(H2O)6]3+(aq) Fe(H2O)3(OH)3(s) No change
Iron (III), Fe 3+
yellow solution
dropwise
brown precipitate
excess

dropwise NaOH or NH3= brown ppt

excess NaOH = no change NH3(aq) NH3(aq)
[Fe(H2O)6]3+(aq) dropwise Fe(H2O)3(OH)3(s) excess No change
excess NH3 = no change
yellow solution brown precipitate

NaOH(aq) NaOH(aq)
[Cu(H2O)6]2+(aq) Cu(H2O)4(OH)2(s) No change
Copper (II), Cu 2+
blue solution
dropwise
blue precipitate
excess

dropwise NaOH or NH3= blue ppt

NH3(aq) NH3(aq)
excess NaOH = no change [Cu(H2O)6]2+(aq) dropwise Cu(H2O)4(OH)2(s) [Cu(NH3)4(H2O)2]2+(aq)
excess
excess NH3 = deep blue solution
blue solution blue precipitate deep blue solution

NaOH(aq) NaOH(aq)

Chromium (III), Cr
[Cr(H2O)6]3+(aq) Cr(H2O)3(OH)3(s) [Cr(OH)6]3-(aq)
3+ dropwise excess
violet solution green precipitate green solution

dropwise NaOH or NH3= green ppt NH3(aq) NH3(aq)

excess NaOH = green solution [Cr(H2O)6]3+(aq) Cr(H2O)3(OH)3(s) [Cr(NH3)6]3+(aq)
dropwise excess
excess NH3 = purple solution
violet solution green precipitate purple solution

NaOH(aq) NaOH(aq)
[Co(H2O)6]2+(aq) Co(H2O)4(OH)2(s) no change

Cobalt (II), Co2+

dropwise excess
pink solution blue precipitate

dropwise NaOH or NH3= blue ppt NH3(aq) NH3(aq)

excess NaOH = no change [Co(H2O)6]2+(aq) dropwise Co(H2O)4(OH)2(s) excess [Co(NH3)6]2+(aq)
excess NH3 = yellow solution
pink solution blue precipitate yellow solution
 Inorganic Revision Sheet
Metal Aqua Ion Reactions for Edexcel

Vanadium Colours
Oxidation State Colour
Can reduce Vanadium from +5 +2 V2+ Purple
oxidation state to +2 using zinc in
acid solution.
+3 V3+ Green
+4 VO2+ Blue
+5 VO2+ Yellow

Ligand Exchange
[Cu(H2O)6]2+(aq) + 4Cl-(aq) [Cu(Cl)4]2-(aq) + 6H2O(l)
Copper (II), Cu 2+
blue solution yellow solution

Cobalt (II), Co 2+ [Co(H2O)6]2+(aq) + 4Cl-(aq) [Co(Cl)4]2-(aq) + 6H2O(l)

pink solution blue precipitate

 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkanes Combustion
REACTANTS: Alkane and O2 (oxygen)
CONDITIONS: Excess of Oxygen (for complete combustion)
PRODUCT(S): Carbon Dioxide and Water
REACTION TYPE: Combustion

REACTION:
(example of
pentane)

NOTES:
• When excess oxygen is present complete combustion occurs so carbon dioxide and water are the
only products.
• Incomplete combustion of alkanes occurs when oxygen becomes a limiting reagent, leading to the
formation of carbon monoxide (CO) and solid carbon particulates (soot).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkanes Free Radical Substitution

REACTANTS: Alkanes and Halogen
CONDITIONS: U.V (ultraviolet) light
PRODUCT: Halogenoalkane
REACTION TYPE: Free Radical Substitution

REACTION:
(example of
methane)

NOTES:
• Chain reaction, occuring in three steps - initiation, propagation and termination. See mechanism.
• U.V light is required to homolytically split halogen molecule, forming two radical species.
• Further substitution can occur, forming di, tri and tetra halogenoalkanes.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution (OH-)

REACTANTS: Halogenoalkane and Sodium Hydroxide, NaOH (for OH- ions)
CONDITIONS: Heat under reflux, Aqueous ('aq' - water present)
PRODUCT(S): Alcohol and Halide Ion (sodium halide salt if sodium hydroxide used)
REACTION TYPE: Nucleophilic Substitution, Hydrolysis

REACTION:
(example of
bromoethane)

NOTES:
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• Rate of hydrolysis can compared using aqueous silver nitrate (AgNO3) within the reaction mixture and
timing how long it takes to form precipitate (Cl = white ppt, Br = cream ppt and I = yellow ppt).
• Reaction must be carried out in aqueous conditions, otherwise an elimination can occur.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution (CN-)

REACTANTS: Halogenoalkane and Sodium or Potassium Cyanide (NaCN or KCN)
CONDITIONS: Heat under reflux, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Nitrile and Halide Ion (forms salt with Na+ or K+)
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
pentane)

NOTES:
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est, giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the nitrile.
• Reaction is heated under reflux to ensure no volatile substances are lost.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution (NH3)

REACTANTS: Halogenoalkane and Ammonia (NH3)
CONDITIONS: Heat*, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Amine and Ammonium Halide Salt
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

NOTES:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the amine.
• *A sealed container (to stop ammonia escaping) containing reactants is heated.
+
• The amine formed in the reaction is a stronger base than ammonia and an ammonium-alkyl [RNH3]
salt may be formed. The amine can be obtained by adding sodium hydroxide to the mixture - forcing
the alkyl-ammonium ion to 'release' a H+ ion and become a neutral molecule.
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est, giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution and Elimination (OH-)

REACTANTS: Halogenoalkane and Potassium Hydroxide (for OH- ions)
CONDITIONS: Heat under reflux, Ethanolic or Aqueous*
PRODUCT(S): Alcohol and Alkene (possible mixture of both)
REACTION TYPE: Nucleophilic Substitution and Elimination

REACTION(S):
(example of
2-bromo-
propane)

NOTES:
• Halogenoalkanes can react with hydroxide (OH ) ions in both substitution and elimation reactions.
-

• If substitution occurs an alcohol is formed, whereas if elimination occurs an alkene is

formed.
• The solvent used can help ensure more of one product is formed than the other, although final prod-
uct mixture can still contain both the alcohol and alkene.
• If a hot aqueous solvent is used, more alcohol forms.
• If a hot ethanolic solvent is used, more alkene forms.
• Primary alcohols are more likely to undergo substitution - tertiary alcohols are more likely to un-
dergo elimination. Secondary alcohols can undergo both substitution and elimination.
• Higher temperatures and a more concentrated solution of hydroxide ions favour elimination.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Addition (HBr)

REACTANTS: Alkene and Hydrogen Bromide (HBr)
CONDITIONS: Hydrogen Bromide Gas or (concentrated) Hydrobromic Acid
PRODUCT(S): Bromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

NOTES:
• For unsymetrical alkenes, there will be two possible products from the electrophilic addition.
• Stability of the carbocation intermediate in the mechanism will determine which product will made
more readily (major product) and which product will be made less readily (minor product). See
mechanism.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Addition (Br2)

REACTANTS: Alkene and Bromine (Br2)
CONDITIONS: Bromine Liquid (pure Br2) or Bromine Water (Br2(aq))
PRODUCT(S): Dibromoalkane
REACTION TYPE: Electrophilic Addition, Bromination

REACTION:
(example of
ethene)

NOTES:
• Double bond in alkene polarises the bromine molecule to form an electrophile (Brδ+) that starts the
reaction.
• Reaction can be used to test for the presence of an alkene. A sample is mixed with bromine water, if
the bromine water turns colourless (from orange - brown) an alkene is present in the sample.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Hydration (to alcohol)

REACTANTS: Alkene and Steam (H2O(g))
CONDITIONS: Heat and Acid Catalyst (Phosphoric Acid, H3PO4)
PRODUCT(S): Alcohol
REACTION TYPE: Electrophilic Addition, (acid catalysed) Hydration

REACTION:
(example of
ethene)

NOTES:
+
• Acid catalyst is required to form hydroxonium ion (H3O ) ion that is able to act as an electrophile to
start the reaction.
• For unsymetrical alkenes, there will be two possible products from the electrophilic addition.
• Stability of the carbocation intermediate in the mechanism will determine which product will made
more readily (major product) and which product will be made less readily (minor product).See
mechanism.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Hydrogenation (to alkane)

REACTANTS: Alkene and Hydrogen, H2
CONDITIONS: Approximately 150oC and Nickel (solid) Catalyst
PRODUCT(S): Alkane
REACTION TYPE: Addition, Hydrogenation

REACTION:
(example of
ethene)

NOTES:
• Hydrogen is 'added' across the double bond - addition reaction and the hydrocarbon becomes satu-
rated (from unsaturated (alkene)).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Oxidation (to form diol)

REACTANTS: Alkene and (dilute) Potassium Manganate (VII)
CONDITIONS: Cold Temperature, Acidic Conditions
PRODUCT(S): Diol
REACTION TYPE: Oxidation

REACTION:
(example of
ethene)

NOTES:
• Oxidation reaction must be carried out in cold temperature with dilute potassium manganate to
ensure the diol doesn't get further oxidised and split in two (forming two carbonyl containing mole-
cules).
• Colour change of the acidified potassium mangangante (VII) - (purple to colourless), can be used
as a test to show a double bond is present (although the bromine water test is simpler and more
specific).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Oxidation (breaking C=C double bond)

REACTANTS: Alkene and (concentrated) Potassium Manganate (VII)
CONDITIONS: Hot Temperature, Acidic Conditions
PRODUCT(S): Two Carbonyl Molecules (split C=C double bond)
REACTION TYPE: Oxidation

REACTION:

NOTES:
• If concentrated potassium manganate (VII) and a high temperature is used, the carbon double bond
in the alkene is broken completely and two new carbonyl groups form (each on a new molecule).
• Depending on the R groups of the original alkene, carboxylic acids can form (if one of the R groups is
H) as an aldehyde formed would be further oxidised to a carboxylic acid.
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Polymers Addition (from alkenes)

REACTANTS: Alkene
PRODUCT(S): Poly(alkene)
REACTION TYPE: Addition Polymerisation

REACTION:
(example of
ethene)

NOTES:
• The carbon-carbon double bond in the alkene breaks, allowing each carbon atom to form a
new bond (with another carbon atom from another molecule).
• The alkenes that form a polymer are called monomers.
• The polymer is made up of repeating units.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alcohols Oxidation
REACTANTS: Alcohol (primary or secondary) and Acidified Dichromate ions (Cr2O72- / H+)
CONDITIONS: Heat*, Acid Catalyst (sulfuric acid (H2SO4))
PRODUCT(S): Aldehyde, Ketone or Carboxylic Acid (see below)
REACTION TYPE: Oxidation

REACTIONS:
(example of
primary and
secondary
alcohol)

NOTES:
• *Primary alcohols form aldehydes and carboxylic acids when heated with an oxidising agent. To iso-
late aldehyde, distill aldehyde from reaction mixture as soon as it is formed. To obtain carboxylic acid,
heat under reflux to ensure full oxidation of aldehydes already formed.
• Secondary alcohols form ketones and are unable to be further oxidised. Tertiary alcohols are unable
to be oxidised at all.
• Oxidising agents can be repesented as [O].
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (PCl5)

REACTANTS: Alcohol and (solid) Phosphorus (V) Pentachloride (PCl5)
CONDITIONS: Pure alcohol (no water must be present)
PRODUCT(S): Chloroalkane and HCl (white fumes)
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• PCl5 reacts vigorously with -OH groups, producing white misty fumes of HCl. Due to this, the sample
of alcohol being halogenated must be pure containing no water or other molecules with an -OH
group.
• The reaction can be used to test for an alcohol (positive result is observation of misty white fumes).
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (KBr)

REACTANTS: Alcohol and 50% (concentrated) H2SO4 and Potassium Bromide, KBr
CONDITIONS: (concentrated) H2SO4, Warm Temperature (for distillation of product)
PRODUCT(S): Bromoalkane
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• KBr and H2SO4 react together to form HBr that reacts with the alcohol to form the bromoalkane.
• Bromoalkane is isolated from the reaction mixture by distillation.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alcohols Elimination (to alkenes)

REACTANTS: Alcohol
CONDITIONS: Heat, Acid Catalyst (concentrated H2SO4 or concentrated H3PO4)
PRODUCT(S): Alkene
REACTION TYPE: Elimination, dehydration

REACTION:
(example of
ethene)

NOTES:
+
• Acid catalyst provides H ion to start reaction and is reformed at the end when a H+ ion is released
by reacting molecule.
• Water molecule is removed, dehydration reaction.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alcohols With Sodium, Na

REACTANTS: Alcohol and Sodium
PRODUCT(S): Alkoxide and Sodium Ion (Na+)

REACTION:
(example of
ethanol)

NOTES:
• Alcohol reacts in a similar way with sodium metal as water. Hydrogen gas is released, the sodium
+
metal becomes a positively charged ion (Na ) and the ROH group becomes a negatively charged
'alkoxide' ion (RO: ).
-

• Ethanol reacts with sodium metal to form sodium ethoxide:

2CH3CH2OH + 2Na → 2CH3CH2O-Na+ + H2
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Aldehydes Reduction (NaBH4)

REACTANTS: Aldehyde and NaBH4 (reducing agent)
PRODUCT(S): Primary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• Aldehydes form primary alcohols when reduced.
• NaBH4 is a reducing agent able to provide hydride (:H-) ions that are needed for the reduction
of carbonyls.
• The hydrogens added in reduction reactions are often shown as [H].
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Ketones Reduction (NaBH4)

REACTANTS: Ketone and NaBH4 (reducing agent)
PRODUCT(S): Secondary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• Ketones form secondary alcohols when reduced.
• NaBH4 is a reducing agent able to provide hydride (:H-) ions that are needed for the reduction
of carbonyls.
• The hydrogens added in reduction reactions are often shown as [H].
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Hydroxynitriles Formation (from carbonyls)

REACTANTS: Carbonyl (aldehyde or ketone) and KCN (in acid)
PRODUCT(S): Hydroxynitrile
REACTION TYPE: Nucleophilic Addition

REACTION:

NOTES:
• HCN is sometimes written as the reactant, but HCN is very reactive and dangerous. By using
KCN in dilute acid, the same product can be formed as with HCN.
• If a chiral carbon centre is formed in the product, the final product mixture will be racemic,
containing both enantiomers in a 50:50 ratio. This is because carbonyl groups are planar and
there is equal chance of the :CN- nucleophile attacking the carbonyl group from above or be-
low the plane - producing two possible enantiomers in equal amounts.
 Organic Chemistry Revision Sheets
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Carboxylic Acids Acid-Base Reactions

Carboxylic acids are able to act as weak acids and react with bases as any weak acid does

NOTES:
• Salts formed by carboxylic acids are (usually) highly soluble in water and can be a useful
source of conjugate bases for making buffer systems.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Carboxylic Acids Reduction (to alcohols using LiAlH4)

REACTANTS: Carboxylic Acid and LiAlH4
CONDITIONS: Dry ether (room temperature)
PRODUCT(S): Primary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• LiAlH4 is used as the reducing agent as NaBH4 isn't powerful enough to reduce the carboxylic acid.
• Reducing agent can be represented as [H] when writing the reaction:
RCOOH + 4[H]→ RCH2OH + H2O
• Reaction must be carried out in dry ether (no water present) as LiAlH4 reacts vigorously with water.
 Organic Chemistry Revision Sheets
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Esters Esterification (carboxylic acid and alcohol)

REACTANTS: Carboxylic Acid and Alcohol
CONDITIONS: Heat under reflux and (concentrated) Sulfuric Acid (H2SO4) catalyst
PRODUCT(S): Ester
REACTION TYPE: Condensation, Esterification

REACTION:

NOTES:
• Reaction is reversible (see hydrolysis of esters), so a (concentrated) acid catalyst is needed to force
the position of equilibrium to the formation of ester.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Esters Hydrolysis
REACTANTS: Ester
CONDITIONS: Warm, Aqueous (with dilute acid or alkali)
PRODUCT(S): Carboxylic Acid (or carboxylate salt) and Alcohol
REACTION TYPE: Hydrolysis

REACTION(S):

NOTES:
-
• If alkaline (OH ) conditions are used, a carboxylate ion is formed and can be isolated by adding a dilute
acid.
• Fats and oils are tri-esters and can be broken down into three fatty acid molecules (carboxylic acids)
and one alcohol molecule (glycerol) by hydrolysis.
• Biodisel can be made by the reaction of oil (tri-ester) with methanol in the presence of an acid catalyst,
forming methyl esters that can be used as a diesel fuel.
 Organic Chemistry Revision Sheets
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Nitriles Acid Hydrolysis (to form carboxylic acids)

REACTANTS: Nitrile and (dilute) Hydrochloric Acid (HCl)
CONDITIONS: Heat under reflux
PRODUCT(S): Carboxylic Acid and Ammonium Chloride
REACTION TYPE: Hydrolysis

REACTION:

NOTES:
• Full reaction:
RCN + 2H2O + HCl → RCOOH + [NH4]+Cl-
• Nitriles can also be hydrolysed in alkaline conditions (heated under reflux) using sodium hy-
droxide, forming the sodium carboxylate salt of the carboxylic acid.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkanes Combustion
REACTANTS: Alkane and O2 (oxygen)
CONDITIONS: Excess of Oxygen (for complete combustion)
PRODUCT(S): Carbon Dioxide and Water
REACTION TYPE: Combustion

REACTION:
(example of
pentane)

NOTES:
• When excess oxygen is present complete combustion occurs so carbon dioxide and water are the
only products.
• Incomplete combustion of alkanes occurs when oxygen becomes a limiting reagent, leading to the
formation of carbon monoxide (CO) and solid carbon particulates (soot).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkanes Free Radical Substitution

REACTANTS: Alkanes and Halogen
CONDITIONS: U.V (ultraviolet) light
PRODUCT: Halogenoalkane
REACTION TYPE: Free Radical Substitution

REACTION:
(example of
methane)

NOTES:
• Chain reaction, occuring in three steps - initiation, propagation and termination. See mechanism.
• U.V light is required to homolytically split halogen molecule, forming two radical species.
• Further substitution can occur, forming di, tri and tetra halogenoalkanes.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution (OH-)

REACTANTS: Halogenoalkane and Sodium Hydroxide, NaOH (for OH- ions)
CONDITIONS: Heat under reflux, Aqueous ('aq' - water present)
PRODUCT(S): Alcohol and Halide Ion (sodium halide salt if sodium hydroxide used)
REACTION TYPE: Nucleophilic Substitution, Hydrolysis

REACTION:
(example of
bromoethane)

NOTES:
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• Rate of hydrolysis can compared using aqueous silver nitrate (AgNO3) within the reaction mixture and
timing how long it takes to form precipitate (Cl = white ppt, Br = cream ppt and I = yellow ppt).
• Reaction must be carried out in aqueous conditions, otherwise an elimination can occur.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution (CN-)

REACTANTS: Halogenoalkane and Sodium or Potassium Cyanide (NaCN or KCN)
CONDITIONS: Heat under reflux, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Nitrile and Halide Ion (forms salt with Na+ or K+)
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
pentane)

NOTES:
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est, giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the nitrile.
• Reaction is heated under reflux to ensure no volatile substances are lost.
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution (NH3)

REACTANTS: Halogenoalkane and Ammonia (NH3)
CONDITIONS: Heat*, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Amine and Ammonium Halide Salt
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

NOTES:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the amine.
• *A sealed container (to stop ammonia escaping) containing reactants is heated.
+
• The amine formed in the reaction is a stronger base than ammonia and an ammonium-alkyl [RNH3]
salt may be formed. The amine can be obtained by adding sodium hydroxide to the mixture - forcing
the alkyl-ammonium ion to 'release' a H+ ion and become a neutral molecule.
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est, giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Halogenoalkanes Substitution and Elimination (OH-)

REACTANTS: Halogenoalkane and Potassium Hydroxide (for OH- ions)
CONDITIONS: Heat under reflux, Ethanolic or Aqueous*
PRODUCT(S): Alcohol and Alkene (possible mixture of both)
REACTION TYPE: Nucleophilic Substitution and Elimination

REACTION(S):
(example of
2-bromo-
propane)

NOTES:
• Halogenoalkanes can react with hydroxide (OH ) ions in both substitution and elimation reactions.
-

• If substitution occurs an alcohol is formed, whereas if elimination occurs an alkene is

formed.
• The solvent used can help ensure more of one product is formed than the other, although final prod-
uct mixture can still contain both the alcohol and alkene.
• If a hot aqueous solvent is used, more alcohol forms.
• If a hot ethanolic solvent is used, more alkene forms.
• Primary alcohols are more likely to undergo substitution - tertiary alcohols are more likely to un-
dergo elimination. Secondary alcohols can undergo both substitution and elimination.
• Higher temperatures and a more concentrated solution of hydroxide ions favour elimination.
 Organic Chemistry Revision Sheets
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Alkenes Addition (HBr)

REACTANTS: Alkene and Hydrogen Bromide (HBr)
CONDITIONS: Hydrogen Bromide Gas or (concentrated) Hydrobromic Acid
PRODUCT(S): Bromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

NOTES:
• For unsymetrical alkenes, there will be two possible products from the electrophilic addition.
• Stability of the carbocation intermediate in the mechanism will determine which product will made
more readily (major product) and which product will be made less readily (minor product). See
mechanism.
 Organic Chemistry Revision Sheets
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Alkenes Addition (Br2)

REACTANTS: Alkene and Bromine (Br2)
CONDITIONS: Bromine Liquid (pure Br2) or Bromine Water (Br2(aq))
PRODUCT(S): Dibromoalkane
REACTION TYPE: Electrophilic Addition, Bromination

REACTION:
(example of
ethene)

NOTES:
• Double bond in alkene polarises the bromine molecule to form an electrophile (Brδ+) that starts the
reaction.
• Reaction can be used to test for the presence of an alkene. A sample is mixed with bromine water, if
the bromine water turns colourless (from orange - brown) an alkene is present in the sample.
 Organic Chemistry Revision Sheets
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Alkenes Hydration (to alcohol)

REACTANTS: Alkene and Steam (H2O(g))
CONDITIONS: Heat and Acid Catalyst (Phosphoric Acid, H3PO4)
PRODUCT(S): Alcohol
REACTION TYPE: Electrophilic Addition, (acid catalysed) Hydration

REACTION:
(example of
ethene)

NOTES:
+
• Acid catalyst is required to form hydroxonium ion (H3O ) ion that is able to act as an electrophile to
start the reaction.
• For unsymetrical alkenes, there will be two possible products from the electrophilic addition.
• Stability of the carbocation intermediate in the mechanism will determine which product will made
more readily (major product) and which product will be made less readily (minor product).See
mechanism.
 Organic Chemistry Revision Sheets
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Alkenes Hydrogenation (to alkane)

REACTANTS: Alkene and Hydrogen, H2
CONDITIONS: Approximately 150oC and Nickel (solid) Catalyst
PRODUCT(S): Alkane
REACTION TYPE: Addition, Hydrogenation

REACTION:
(example of
ethene)

NOTES:
• Hydrogen is 'added' across the double bond - addition reaction and the hydrocarbon becomes satu-
rated (from unsaturated (alkene)).
 Organic Chemistry Revision Sheets
Reactions for CIE A-Level Chemistry

Alkenes Oxidation (to form diol)

REACTANTS: Alkene and (dilute) Potassium Manganate (VII)
CONDITIONS: Cold Temperature, Acidic Conditions
PRODUCT(S): Diol
REACTION TYPE: Oxidation

REACTION:
(example of
ethene)

NOTES:
• Oxidation reaction must be carried out in cold temperature with dilute potassium manganate to
ensure the diol doesn't get further oxidised and split in two (forming two carbonyl containing mole-
cules).
• Colour change of the acidified potassium mangangante (VII) - (purple to colourless), can be used
as a test to show a double bond is present (although the bromine water test is simpler and more
specific).
 Organic Chemistry Revision Sheets
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Alkenes Oxidation (breaking C=C double bond)

REACTANTS: Alkene and (concentrated) Potassium Manganate (VII)
CONDITIONS: Hot Temperature, Acidic Conditions
PRODUCT(S): Two Carbonyl Molecules (split C=C double bond)
REACTION TYPE: Oxidation

REACTION:

NOTES:
• If concentrated potassium manganate (VII) and a high temperature is used, the carbon double bond
in the alkene is broken completely and two new carbonyl groups form (each on a new molecule).
• Depending on the R groups of the original alkene, carboxylic acids can form (if one of the R groups is
H) as an aldehyde formed would be further oxidised to a carboxylic acid.
 Organic Chemistry Revision Sheets
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Polymers Addition (from alkenes)

REACTANTS: Alkene
PRODUCT(S): Poly(alkene)
REACTION TYPE: Addition Polymerisation

REACTION:
(example of
ethene)

NOTES:
• The carbon-carbon double bond in the alkene breaks, allowing each carbon atom to form a
new bond (with another carbon atom from another molecule).
• The alkenes that form a polymer are called monomers.
• The polymer is made up of repeating units.
 Organic Chemistry Revision Sheets
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Alcohols Oxidation
REACTANTS: Alcohol (primary or secondary) and Acidified Dichromate ions (Cr2O72- / H+)
CONDITIONS: Heat*, Acid Catalyst (sulfuric acid (H2SO4))
PRODUCT(S): Aldehyde, Ketone or Carboxylic Acid (see below)
REACTION TYPE: Oxidation

REACTIONS:
(example of
primary and
secondary
alcohol)

NOTES:
• *Primary alcohols form aldehydes and carboxylic acids when heated with an oxidising agent. To iso-
late aldehyde, distill aldehyde from reaction mixture as soon as it is formed. To obtain carboxylic acid,
heat under reflux to ensure full oxidation of aldehydes already formed.
• Secondary alcohols form ketones and are unable to be further oxidised. Tertiary alcohols are unable
to be oxidised at all.
• Oxidising agents can be repesented as [O].
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (PCl5)

REACTANTS: Alcohol and (solid) Phosphorus (V) Pentachloride (PCl5)
CONDITIONS: Pure alcohol (no water must be present)
PRODUCT(S): Chloroalkane and HCl (white fumes)
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• PCl5 reacts vigorously with -OH groups, producing white misty fumes of HCl. Due to this, the sample
of alcohol being halogenated must be pure containing no water or other molecules with an -OH
group.
• The reaction can be used to test for an alcohol (positive result is observation of misty white fumes).
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (KBr)

REACTANTS: Alcohol and 50% (concentrated) H2SO4 and Potassium Bromide, KBr
CONDITIONS: (concentrated) H2SO4, Warm Temperature (for distillation of product)
PRODUCT(S): Bromoalkane
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• KBr and H2SO4 react together to form HBr that reacts with the alcohol to form the bromoalkane.
• Bromoalkane is isolated from the reaction mixture by distillation.
 Organic Chemistry Revision Sheets
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Alcohols Elimination (to alkenes)

REACTANTS: Alcohol
CONDITIONS: Heat, Acid Catalyst (concentrated H2SO4 or concentrated H3PO4)
PRODUCT(S): Alkene
REACTION TYPE: Elimination, dehydration

REACTION:
(example of
ethene)

NOTES:
+
• Acid catalyst provides H ion to start reaction and is reformed at the end when a H+ ion is released
by reacting molecule.
• Water molecule is removed, dehydration reaction.
 Organic Chemistry Revision Sheets
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Alcohols With Sodium, Na

REACTANTS: Alcohol and Sodium
PRODUCT(S): Alkoxide and Sodium Ion (Na+)

REACTION:
(example of
ethanol)

NOTES:
• Alcohol reacts in a similar way with sodium metal as water. Hydrogen gas is released, the sodium
+
metal becomes a positively charged ion (Na ) and the ROH group becomes a negatively charged
'alkoxide' ion (RO: ).
-

• Ethanol reacts with sodium metal to form sodium ethoxide:

2CH3CH2OH + 2Na → 2CH3CH2O-Na+ + H2
 Organic Chemistry Revision Sheets
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Aldehydes Reduction (NaBH4)

REACTANTS: Aldehyde and NaBH4 (reducing agent)
PRODUCT(S): Primary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• Aldehydes form primary alcohols when reduced.
• NaBH4 is a reducing agent able to provide hydride (:H-) ions that are needed for the reduction
of carbonyls.
• The hydrogens added in reduction reactions are often shown as [H].
 Organic Chemistry Revision Sheets
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Ketones Reduction (NaBH4)

REACTANTS: Ketone and NaBH4 (reducing agent)
PRODUCT(S): Secondary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• Ketones form secondary alcohols when reduced.
• NaBH4 is a reducing agent able to provide hydride (:H-) ions that are needed for the reduction
of carbonyls.
• The hydrogens added in reduction reactions are often shown as [H].
 Organic Chemistry Revision Sheets
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Hydroxynitriles Formation (from carbonyls)

REACTANTS: Carbonyl (aldehyde or ketone) and KCN (in acid)
PRODUCT(S): Hydroxynitrile
REACTION TYPE: Nucleophilic Addition

REACTION:

NOTES:
• HCN is sometimes written as the reactant, but HCN is very reactive and dangerous. By using
KCN in dilute acid, the same product can be formed as with HCN.
• If a chiral carbon centre is formed in the product, the final product mixture will be racemic,
containing both enantiomers in a 50:50 ratio. This is because carbonyl groups are planar and
there is equal chance of the :CN- nucleophile attacking the carbonyl group from above or be-
low the plane - producing two possible enantiomers in equal amounts.
 Organic Chemistry Revision Sheets
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Carboxylic Acids Acid-Base Reactions

Carboxylic acids are able to act as weak acids and react with bases as any weak acid does

NOTES:
• Salts formed by carboxylic acids are (usually) highly soluble in water and can be a useful
source of conjugate bases for making buffer systems.
 Organic Chemistry Revision Sheets
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Carboxylic Acids Reduction (to alcohols using LiAlH4)

REACTANTS: Carboxylic Acid and LiAlH4
CONDITIONS: Dry ether (room temperature)
PRODUCT(S): Primary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• LiAlH4 is used as the reducing agent as NaBH4 isn't powerful enough to reduce the carboxylic acid.
• Reducing agent can be represented as [H] when writing the reaction:
RCOOH + 4[H]→ RCH2OH + H2O
• Reaction must be carried out in dry ether (no water present) as LiAlH4 reacts vigorously with water.
 Organic Chemistry Revision Sheets
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Esters Esterification (carboxylic acid and alcohol)

REACTANTS: Carboxylic Acid and Alcohol
CONDITIONS: Heat under reflux and (concentrated) Sulfuric Acid (H2SO4) catalyst
PRODUCT(S): Ester
REACTION TYPE: Condensation, Esterification

REACTION:

NOTES:
• Reaction is reversible (see hydrolysis of esters), so a (concentrated) acid catalyst is needed to force
the position of equilibrium to the formation of ester.
 Organic Chemistry Revision Sheets
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Esters Hydrolysis
REACTANTS: Ester
CONDITIONS: Warm, Aqueous (with dilute acid or alkali)
PRODUCT(S): Carboxylic Acid (or carboxylate salt) and Alcohol
REACTION TYPE: Hydrolysis

REACTION(S):

NOTES:
-
• If alkaline (OH ) conditions are used, a carboxylate ion is formed and can be isolated by adding a dilute
acid.
• Fats and oils are tri-esters and can be broken down into three fatty acid molecules (carboxylic acids)
and one alcohol molecule (glycerol) by hydrolysis.
• Biodisel can be made by the reaction of oil (tri-ester) with methanol in the presence of an acid catalyst,
forming methyl esters that can be used as a diesel fuel.
 Organic Chemistry Revision Sheets
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Nitriles Acid Hydrolysis (to form carboxylic acids)

REACTANTS: Nitrile and (dilute) Hydrochloric Acid (HCl)
CONDITIONS: Heat under reflux
PRODUCT(S): Carboxylic Acid and Ammonium Chloride
REACTION TYPE: Hydrolysis

REACTION:

NOTES:
• Full reaction:
RCN + 2H2O + HCl → RCOOH + [NH4]+Cl-
• Nitriles can also be hydrolysed in alkaline conditions (heated under reflux) using sodium hy-
droxide, forming the sodium carboxylate salt of the carboxylic acid.
 Organic Chemistry Revision Sheets
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Alkanes Combustion
REACTANTS: Alkane and O2 (oxygen)
CONDITIONS: Excess of Oxygen (for complete combustion)
PRODUCT(S): Carbon Dioxide and Water
REACTION TYPE: Combustion

REACTION:
(example of
pentane)

NOTES:
• When excess oxygen is present complete combustion occurs so carbon dioxide and water are the
only products.
• Incomplete combustion of alkanes occurs when oxygen becomes a limiting reagent, leading to the
formation of carbon monoxide (CO) and solid carbon particulates (soot).
 Organic Chemistry Revision Sheets
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Alkanes Free Radical Substitution

REACTANTS: Alkanes and Halogen
CONDITIONS: U.V (ultraviolet) light
PRODUCT: Halogenoalkane
REACTION TYPE: Free Radical Substitution

REACTION:
(example of
methane)

NOTES:
• Chain reaction, occuring in three steps - initiation, propagation and termination. See mechanism.
• U.V light is required to homolytically split halogen molecule, forming two radical species.
• Further substitution can occur, forming di, tri and tetra halogenoalkanes.
 Organic Chemistry Revision Sheets
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Halogenoalkanes Substitution (OH-)

REACTANTS: Halogenoalkane and Sodium Hydroxide, NaOH (for OH- ions)
CONDITIONS: Heat under reflux, Aqueous ('aq' - water present)
PRODUCT(S): Alcohol and Halide Ion (sodium halide salt if sodium hydroxide used)
REACTION TYPE: Nucleophilic Substitution, Hydrolysis

REACTION:
(example of
bromoethane)

NOTES:
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• Rate of hydrolysis can compared using aqueous silver nitrate (AgNO3) within the reaction mixture and
timing how long it takes to form precipitate (Cl = white ppt, Br = cream ppt and I = yellow ppt).
• Reaction must be carried out in aqueous conditions, otherwise an elimination can occur.
 Organic Chemistry Revision Sheets
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Halogenoalkanes Substitution (CN-)

REACTANTS: Halogenoalkane and Sodium or Potassium Cyanide (NaCN or KCN)
CONDITIONS: Heat under reflux, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Nitrile and Halide Ion (forms salt with Na+ or K+)
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
pentane)

NOTES:
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est, giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the nitrile.
• Reaction is heated under reflux to ensure no volatile substances are lost.
 Organic Chemistry Revision Sheets
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Halogenoalkanes Substitution (NH3 and amines)

REACTANTS: Halogenoalkane and Ammonia (NH3)
CONDITIONS: Heat*, Ethanolic (ethanol as the solvent, no water present)
PRODUCT(S): Amine and Ammonium Halide Salt
REACTION TYPE: Nucleophilic Substitution

REACTION:
(example of
bromoethane)

NOTES:
• Reaction must be carried out in ethanolic conditions (in ethanol, no water present), otherwise
an alcohol is likely to form rather than the amine.
• *A sealed container (to stop ammonia escaping) containing reactants is heated.
• The amine formed in the reaction is actually a stronger base than ammonia and an ammonium-alkyl
salt may be formed. The amine can be obtained by adding sodium hydroxide to the mixture - forcing
the alkyl-ammonium ion to 'release' a H+ ion and become a neutral molecule.
• Rate of reaction is determined by strength of carbon-halogen bond (carbon-flourine bond is strong-
est, giving slowest rate; carbon-iodine bond is weakest, giving fastest rate).
• If an amine is used instead of ammonia, a secondary amine can be formed. For example, the reac-
tion of butylamine with 2-bromoethane:
CH3CH2CH2CH2NH2 + CH3CH2Br → CH3CH2CH2CH2NHCH2CH3 (ethylbutylamine) + HBr
 Organic Chemistry Revision Sheets
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Halogenoalkanes Substitution and Elimination (OH-)

REACTANTS: Halogenoalkane and Potassium Hydroxide (for OH- ions)
CONDITIONS: Heat under reflux, Ethanolic or Aqueous*
PRODUCT(S): Alcohol and Alkene (possible mixture of both)
REACTION TYPE: Nucleophilic Substitution and Elimination

REACTION(S):
(example of
2-bromo-
propane)

NOTES:
• Halogenoalkanes can react with hydroxide (OH ) ions in both substitution and elimination reactions.
-

• If substitution occurs an alcohol is formed, whereas if elimination occurs an alkene is

formed.
• The solvent used can help ensure more of one product is formed than the other, although final prod-
uct mixture can still contain both the alcohol and alkene.
• If a hot aqueous solvent is used, more alcohol forms.
• If a hot ethanolic solvent is used, more alkene forms.
• Primary alcohols are more likely to undergo substitution - tertiary alcohols are more likely to un-
dergo elimination. Secondary alcohols can undergo both substitution and elimination.
• Higher temperatures and a more concentrated solution of hydroxide ions favour elimination.
 Organic Chemistry Revision Sheets
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Alkenes Addition (HBr)

REACTANTS: Alkene and Hydrogen Bromide (HBr)
CONDITIONS: Hydrogen Bromide Gas or (concentrated) Hydrobromic Acid
PRODUCT(S): Bromoalkane
REACTION TYPE: Electrophilic Addition

REACTION:
(example of
ethene)

NOTES:
• For unsymetrical alkenes, there will be two possible products from the electrophilic addition.
• Stability of the carbocation intermediate in the mechanism will determine which product will made
more readily (major product) and which product will be made less readily (minor product). See
mechanism.
 Organic Chemistry Revision Sheets
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Alkenes Addition (Br2)

REACTANTS: Alkene and Bromine (Br2)
CONDITIONS: Bromine Liquid (pure Br2) or Bromine Water (Br2(aq))
PRODUCT(S): Dibromoalkane
REACTION TYPE: Electrophilic Addition, Bromination

REACTION:
(example of
ethene)

NOTES:
• Double bond in alkene polarises the bromine molecule to form an electrophile (Brδ+) that starts the
reaction.
• Reaction can be used to test for the presence of an alkene. A sample is mixed with bromine water, if
the bromine water turns colourless (from orange - brown) an alkene is present in the sample.
 Organic Chemistry Revision Sheets
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Alkenes Hydration (to alcohol)

REACTANTS: Alkene and Steam (H2O(g))
CONDITIONS: Heat and Acid Catalyst (Phosphoric Acid, H3PO4)
PRODUCT(S): Alcohol
REACTION TYPE: Electrophilic Addition, (acid catalysed) Hydration

REACTION:
(example of
ethene)

NOTES:
+
• Acid catalyst is required to form hydroxonium ion (H3O ) ion that is able to act as an electrophile to
start the reaction.
• For unsymetrical alkenes, there will be two possible products from the electrophilic addition.
• Stability of the carbocation intermediate in the mechanism will determine which product will made
more readily (major product) and which product will be made less readily (minor product).See
mechanism.
 Organic Chemistry Revision Sheets
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Alkenes Hydrogenation (to alkane)

REACTANTS: Alkene and Hydrogen, H2
CONDITIONS: Approximately 150oC and Nickel (solid) Catalyst
PRODUCT(S): Alkane
REACTION TYPE: Addition, Hydrogenation

REACTION:
(example of
ethene)

NOTES:
• Hydrogen is 'added' across the double bond - addition reaction and the hydrocarbon becomes satu-
rated (from unsaturated (alkene)).
 Organic Chemistry Revision Sheets
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Alkenes Oxidation (to form diol)

REACTANTS: Alkene and (dilute) Potassium Manganate (VII)
CONDITIONS: Cold Temperature, Acidic Conditions
PRODUCT(S): Diol
REACTION TYPE: Oxidation

REACTION:
(example of
ethene)

NOTES:
• Oxidation reaction must be carried out in cold temperature with dilute potassium manganate to
ensure the diol doesn't get further oxidised and split in two (forming two carbonyl containing mole-
cules).
• Colour change of the acidified potassium mangangante (VII) - (purple to colourless), can be used
as a test to show a double bond is present (although the bromine water test is simpler and more
specific).
 Organic Chemistry Revision Sheets
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Alcohols Oxidation
REACTANTS: Alcohol (primary or secondary) and Acidified Dichromate ions (Cr2O72- / H+)
CONDITIONS: Heat*, Acid Catalyst (sulfuric acid (H2SO4))
PRODUCT(S): Aldehyde, Ketone or Carboxylic Acid (see below)
REACTION TYPE: Oxidation

REACTIONS:
(example of
primary and
secondary
alcohol)

NOTES:
• *Primary alcohols form aldehydes and carboxylic acids when heated with an oxidising agent. To iso-
late aldehyde, distill aldehyde from reaction mixture as soon as it is formed. To obtain carboxylic acid,
heat under reflux to ensure full oxidation of aldehydes already formed.
• Secondary alcohols form ketones and are unable to be further oxidised. Tertiary alcohols are unable
to be oxidised at all.
• Oxidising agents can be repesented as [O].
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (PCl5)

REACTANTS: Alcohol and (solid) Phosphorus (V) Pentachloride (PCl5)
CONDITIONS: Pure alcohol (no water must be present)
PRODUCT(S): Chloroalkane and HCl (white fumes)
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• PCl5 reacts vigorously with -OH groups, producing white misty fumes of HCl. Due to this, the sample
of alcohol being halogenated must be pure containing no water or other molecules with an -OH
group.
• The reaction can be used to test for an alcohol (positive result is observation of misty white fumes).
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (KBr)

REACTANTS: Alcohol and 50% (concentrated) H2SO4 and Potassium Bromide, KBr
CONDITIONS: (concentrated) H2SO4, Warm Temperature (for distillation of product)
PRODUCT(S): Bromoalkane
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• KBr and H2SO4 react together to form HBr that reacts with the alcohol to form the bromoalkane.
• Bromoalkane is isolated from the reaction mixture by distillation.
 Organic Chemistry Revision Sheets
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Alcohols Halogenation (Iodine and Red Phosphorus)

REACTANTS: Alcohol, Red Phosphorus and Iodine (I2)
CONDITIONS: Heat under reflux (distillation to isolate product)
PRODUCT(S): Iodoalkane
REACTION TYPE: Halogenation

REACTIONS:
(example of
ethanol)

NOTES:
• Red phosphorus and iodine react together to form phosphorus (III) triiodide that reacts with the alco-
hol to form the iodoalkane.
2P + 3I2 → 2PI3 then 3ROH + PI3 → 3RI + H3PO3
• Final product is isolated from reaction mixture by distillation.
 Organic Chemistry Revision Sheets
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Alcohols Elimination (to alkenes)

REACTANTS: Alcohol
CONDITIONS: Heat, Acid Catalyst (concentrated H2SO4 or concentrated H3PO4)
PRODUCT(S): Alkene
REACTION TYPE: Elimination, dehydration

REACTION:
(example of
ethene)

NOTES:
+
• Acid catalyst provides H ion to start reaction and is reformed at the end when a H+ ion is released
by reacting molecule.
• Water molecule is removed, dehydration reaction.
 Organic Chemistry Revision Sheets
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Ketones Reduction (LiAlH4)

REACTANTS: Ketone and LiAlH4 (reducing agent)
CONDITIONS: Dry Ether
PRODUCT(S): Secondary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• Ketones form secondary alcohols when reduced.
• LiAlH4 is a reducing agent able to provide hydride (:H-) ions that are needed for the reduction
of carbonyls. The reaction must be carried out in dry ether as LiAlH4 reacts vigorously
with water.
• The hydrogens added in reduction reactions are often shown as [H].
 Organic Chemistry Revision Sheets
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Aldehydes Reduction (LiAlH4)

REACTANTS: Aldehyde and LiAlH4 (reducing agent)
CONDITIONS: Dry Ether
PRODUCT(S): Primary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• Aldehydes form primary alcohols when reduced.
• LiAlH4 is a reducing agent able to provide hydride (:H-) ions that are needed for the reduction
of carbonyls. The reaction must be carried out in dry ether as LiAlH4 reacts vigorously
with water.
• The hydrogens added in reduction reactions are often shown as [H].
 Organic Chemistry Revision Sheets
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Hydroxynitriles Formation (from carbonyls)

REACTANTS: Carbonyl (aldehyde or ketone) and KCN (in acid)
PRODUCT(S): Hydroxynitrile
REACTION TYPE: Nucleophilic Addition

REACTION:

NOTES:
• HCN is sometimes written as the reactant, but HCN is very reactive and dangerous. By using
KCN in dilute acid, the same product can be formed as with HCN.
• If a chiral carbon centre is formed in the product, the final product mixture will be racemic,
containing both enantiomers in a 50:50 ratio. This is because carbonyl groups are planar and
there is equal chance of the :CN- nucleophile attacking the carbonyl group from above or be-
low the plane - producing two possible enantiomers in equal amounts.
 Organic Chemistry Revision Sheets
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Carboxylic Acids Acid-Base Reactions

Carboxylic acids are able to act as weak acids and react with bases as any weak acid does

NOTES:
• Salts formed by carboxylic acids are (usually) highly soluble in water and can be a useful
source of conjugate bases for making buffer systems.
 Organic Chemistry Revision Sheets
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Carboxylic Acids Reduction (to alcohols using LiAlH4)

REACTANTS: Carboxylic Acid and LiAlH4
CONDITIONS: Dry ether (room temperature)
PRODUCT(S): Primary Alcohol
REACTION TYPE: Reduction

REACTION:

NOTES:
• LiAlH4 is used as the reducing agent as NaBH4 isn't powerful enough to reduce the carboxylic acid.
• Reducing agent can be represented as [H] when writing the reaction:
RCOOH + 4[H]→ RCH2OH + H2O
• Reaction must be carried out in dry ether (no water present) as LiAlH4 reacts vigorously with water.
 Organic Chemistry Revision Sheets
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Carboxylic Acids Substitution (to acyl chlorides)

REACTANTS: Carboxylic Acid and Phosphorus (V) Pentachloride, PCl5
CONDITIONS: Cold Temperature to Room Temperature
PRODUCT(S): Acyl Chloride
REACTION TYPE: Nucleophilic Substitution

REACTION:

NOTES:
• White misty fumes of HCl are released, making this a useful reaction to identiy a carboxylic acid.
• The acyl chloride can be isolated from the reaction mixture using fractional distillation.
 Organic Chemistry Revision Sheets
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Esters Esterification (carboxylic acid and alcohol)

REACTANTS: Carboxylic Acid and Alcohol
CONDITIONS: Heat under reflux and (concentrated) Sulfuric Acid (H2SO4) catalyst
PRODUCT(S): Ester
REACTION TYPE: Condensation, Esterification

REACTION:

NOTES:
• Reaction is reversible (see hydrolysis of esters), so a (concentrated) acid catalyst is needed to force
the position of equilibrium to the formation of ester.
 Organic Chemistry Revision Sheets
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Esters Hydrolysis
REACTANTS: Ester
CONDITIONS: Warm, Aqueous (with dilute acid or alkali)
PRODUCT(S): Carboxylic Acid (or carboxylate salt) and Alcohol
REACTION TYPE: Hydrolysis

REACTION(S):

NOTES:
-
• If alkaline (OH ) conditions are used, a carboxylate ion is formed and can be isolated by adding a dilute
acid.
• Fats and oils are tri-esters and can be broken down into three fatty acid molecules (carboxylic acids)
and one alcohol molecule (glycerol) by hydrolysis.
• Biodisel can be made by the reaction of oil (tri-ester) with methanol in the presence of an acid catalyst,
forming methyl esters that can be used as a diesel fuel.
 Organic Chemistry Revision Sheets
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Acyl Chlorides Addition-Elimination (H2O)

REACTANTS: Acyl Chloride and H2O
PRODUCT(S): Carboxylic Acid and HCl
REACTION TYPE: Nucleophilic Addition-Elimination, Hydrolysis of acyl chloride

REACTION:

NOTES:
• Acyl chlorides are highly reactive and the reaction is vigorous, with heat given off (exothermic)
and fumes of HCl released.
 Organic Chemistry Revision Sheets
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Acyl Chlorides Addition-Elimination (alcohol)

REACTANTS: Acyl Chloride and Alcohol
PRODUCT(S): Ester and HCl
REACTION TYPE: Nucleophilic Addition-Elimination, Esterification

REACTION:

NOTES:
• Ester formed (esterification) has a sweet, fruity smell.
 Organic Chemistry Revision Sheets
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Acyl Chlorides Addition-Elimination (NH3)

REACTANTS: Acyl Chloride and Ammonia
PRODUCT(S): Amide and Ammonium Chloride (salt)
REACTION TYPE: Nucleophilic Addition-Elimination

REACTION:

NOTES:
• Ammonia produces a primary amide and ammonium chloride salt when reacted with acyl
chlorides.
• Primary amines produce a secondary amide and an alkyl ammonium chloride salt when
reacted with acyl chlorides.
• Secondary amines produce a tertiary amide and an alkyl ammonium chloride salt when re-
acted with acyl chlorides.
 Organic Chemistry Revision Sheets
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Acyl Chlorides Addition-Elimination (amine)

REACTANTS: Acyl Chloride and Amine (primary)
PRODUCT(S): (Secondary) Amide and Alkyl Ammonium Chloride
REACTION TYPE: Nucleophilic Addition-Elimination

REACTION:

NOTES:
• Primary amines produce a secondary amide and an alkyl ammonium chloride salt when
reacted with acyl chlorides.
• Secondary amines produce a tertiary amide and an alkyl ammonium chloride salt when re-
acted with acyl chlorides.
• Butylamine with ethanoyl chloride:
CH3CH2CH2CH2NH2 + CH3COCl → CH3CONHCH2CH2CH2CH3 (N-butylethanamide) + HCl
 Organic Chemistry Revision Sheets
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Benzene Nitration (adding NO2)

REACTANTS: Benzene and (concentrated) Nitric Acid (HNO3)
CONDITIONS: (Concentrated) Sulfuric Acid (H2SO4)
PRODUCT(S): Nitrobenzene
REACTION TYPE: Electrophilic Substitution, Nitration

REACTION:
(example of
benzene)

NOTES:
• Nitronium ion is formed by the reaction of concentrated nitric acid with concentrated sulfuric acid.

• H+ ion removed from benzene ring combines with hydrogen sulfate (HSO4-) ion
to reform catalyst H2SO4.
 Organic Chemistry Revision Sheets
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Benzene Acylation (with acyl chlorides)

REACTANTS: Benzene and Acyl Chloride
CONDITIONS: Warm and AlCl3 catalyst
PRODUCT(S): (Aromatic) Ketone
REACTION TYPE: Electrophilic Substitution, Acylation (Friedel Crafts)

REACTION:
(example of
benzene)

NOTES:
• Acylium (RCO+) ion is formed by reacting an acyl chloride with a halogen carrier (AlCl3).

• H+ ion removed from benzene ring combines with [AlCl4]- to reform AlCl3 catalyst and form
HCl.
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Benzene Alkylation (with halogenoalkanes)

REACTANTS: Benzene and Halogenoalkane
CONDITIONS: Warm and AlCl3 (or AlBr3) catalyst
PRODUCT(S): Alkylbenzene
REACTION TYPE: Electrophilic Substitution, Alkylation (Friedel-Crafts)

REACTION:
(example of
benzene)

NOTES:
• Alkyl (R+) ion is formed by reacting an acyl chloride with a halogen carrier (AlCl3).

• H+ ion removed from benzene ring combines with [AlCl4]- to reform AlCl3 catalyst and form HCl.
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Nitriles Reduction (to form primary amine)

REACTANTS: Nitrile and Reducing Agent - LiAlH4, or Hydrogen gas (H2(g))
CONDITIONS: Dry ether* (if using LiAlH4), Nickel catalyst (if using H2(g))
PRODUCT(S): Amine
REACTION TYPE: Reduction, Hydrogenation

REACTION:

NOTES:
• If H2(g) and a nickel catalyst is used, the reaction is an example of catalytic hydrogenation.
• *Dry ether must be used with LiAlH4 (LiAlH4 reacts violently with water). To obtain the amine as
a final product, dilute acid must be added to the inital product from reduction.
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Nitroarenes Reduction (to form aromatic amines)

REACTANTS: Nitroarene and (concentrated) Hydrochloric Acid (HCl), followed by NaOH
CONDITIONS: Tin catalyst
PRODUCT(S): Aromatic Amine
REACTION TYPE: Reduction

REACTION:
(example of
nitrobenzene)

NOTES:
• When reacted with concentrated HCl, the nitroarene will form an ammonium ion -NH3+. The
aromatic amine can be obtained by adding dilute sodium hydroxide (to form -NH2).
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Polymers Condensation (from dicarboxylic acids and diols)

REACTANTS: Dicarboxylic Acid and Diol
PRODUCT(S): Polyester
REACTION TYPE: Condensation Polymerisation

REACTION:

NOTES:
• Polymer formed is a polyester due to ester link between one dicarboxylic acid group and one
diol group.
• Condensation polymerisation as water is released when polymer is formed.
• Polyesters are broken apart into dicarboxylic acids and diols by hydrolysis reactions (addition
of water) which means they are biodegradable (unlike addition polymers).
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Phenol Bromination (Br2)

REACTANTS: Phenol and Bromine water (Br2(aq))
PRODUCT(S): 2,4,6-tribromopenol
REACTION TYPE: Electrophilic Substitution, Bromination

REACTION:
(example of
phenol)

NOTES:
• Bromine water changes from orange-brown to colourless and a white precipitate forms.
• Unlike with benzene, no halogen carrier catalyst is needed for the bromination of phenol. This
is due to the increased electron density in the delocalised electron ring (from the -OH group),
making phenol more reactive than benzene.
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Amines Acting as Bases (with Cu2+(aq))

REACTANTS: Amine and Copper (II) Ions (Cu2+)
PRODUCT(S): Copper (II) Hydroxide and [Cu(RNH2)4(H2O)2]2+
REACTION TYPE: Acid-Base, Ligand Substitution

REACTION:

NOTES:
• When added dropwise, amine acts a base. The nitrogen atom in amine has a lone pair of
electrons that can act as a base and accept a H+ ion from a water ligand in [Cu(H2O)6]2+ aqua
complex ion, forming blue, solid percipitate of Cu(OH)2.
• If higher amounts of amine are used, ligand substitution occurs and four amine groups swap
places with four water ligands in aqua complex. Blue precipitate formed above redissolves.
• Butylamine with [Cu(H2O)6]2+:
4CH3CH2CH2CH2NH2 + [Cu(H2O)6]2+ → [Cu(H2O)2(CH3CH2CH2CH2NH2)4]2+ + 4H2O
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Amines Acting as Bases (with acids)

REACTANTS: Amine and Acid
PRODUCT(S): Alkyl Ammonium Salt
REACTION TYPE: Acid-Base

REACTION:

NOTES:
• Nitrogen atom in amine has lone pair of electrons that can act as a base and accept a H+ ion
in an acidic solution, forming an alkyl ammonium salt (with the negative ion from the acid).
• Butylamine with hydrochloric acid:
CH3CH2CH2CH2NH2 + HCl → [CH3CH2CH2CH2NH3]+Cl- (butylammonium chloride)
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Amines Acting as Bases (with H2O)

REACTANTS: Amine and Water
PRODUCT(S): Alkyl Ammonium Ion and Hydroxide Ion (OH-)
REACTION TYPE: Acid-Base

REACTION:

NOTES:
• Nitrogen atom in amine has lone pair of electrons that can act as a base and accept a H+ ion
from a water molecule, forming an alkyl ammonium ion and a hydroxide ion.
• Butylamine with water:
CH3CH2CH2CH2NH2 + H2O → [CH3CH2CH2CH2NH3]+ + [OH]-
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Polymers Condensation (from dicarboxylic acids and diamines)

REACTANTS: Dicarboxylic Acid and Diamine
PRODUCT(S): Polyamide
REACTION TYPE: Condensation Polymerisation

REACTION:

NOTES:
• Polymer formed is a polyamide due to the amide group in the repeating unit (formed when one
dicarboxylic acid reacts with a diamine).
• Condensation polymerisation as water is released when polymer is formed.
• Polyesters are broken apart into dicarboxylic acids and diamines by hydrolysis reactions
(addition of water), which means they are biodegradable (unlike addition polymers).
 Organic Chemistry Revision Sheets
Reactions for Edexcel A-Level Chemistry

Amino Acids Condensation Polymerisation (form proteins)

REACTANTS: Amino Acids
PRODUCT(S): Polyamide (polypeptide)
REACTION TYPE: Condensation Polymerisation

REACTION:

NOTES:
• Polymer formed is a polyamide, often referred to as a polypeptide in biology.
• Polyamide chains formed by amino acids are used in nature to make up proteins.
• DNA is a 'code' used by organisms to give the correct amino acid sequence for a particular
protein. A section of DNA that codes for a given protein is called a gene.
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (SN1)

Reaction
REACTANTS: Halogenoalkane and Nucleophile
REACTION TYPE: Nucleophilic Substitution, SN1

REACTION:
(example of
2-bromo-2-meth-
ylpropane)

Mechanism
The first step of the SN1 mechanism is the breaking of the carbon-halogen bond in the
halogenoalkane, forming a carbocation. The nucleophile is then able to form a bond with
the carbocation.

Notes:
• The SN1 reaction occurs (usually) with tertiary halogenoalkanes and only slightly with second-
ary halogenoalkanes. This is because the carbon-halogen bond is too 'crowded' by alkyl groups for
the nucleophile to attack the partially positive carbon directly.
• SN1 reaction is slower than SN2 reaction.
• SN2 reaction occurs mainly with primary halogenoalkanes (and, to a lesser extent, secondary halog-
enoalkanes).
 Organic Chemistry Revision Sheets
Halogenoalkanes | Nucleophilic Substitution (SN2)

Reaction
REACTANTS: Halogenoalkane and Nucleophile
REACTION TYPE: Nucleophilic Substitution, SN2

REACTION:
(example of
bromoethane)

Mechanism
SN2 reaction mechanisms have only one step. The nucleophile attacks the carbon-halogen
bond directly, forming a new carbon-nucleophile bond as the carbon-halogen bond breaks.

Notes:
• The SN2 reaction occurs (usually) with primary halogenoalkanes and only slightly with sec-
ondary halogenoalkanes. This is because the carbon-halogen bond in the primary halogenoalkane is
more available for the nucleophile to attack than the partially positive carbon directly.
• SN2 reaction is faster than SN1 reaction.
• SN1 reaction occurs mainly with tertiary halogenoalkanes (and, to a lesser extent, secondary halog-
enoalkanes).