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ORGANIC CHEMISTRY BIBLE OF CHEMICAL REACTIONS
This bible includes chemical reactions that are covered in the ZIMSEC Advanced Level syllabus.
Reactions of Alkanes
Type of reaction reagents Conditions Main products Example
Oxygen CO2 and H2O 2C2H6 + 7O2 4CO2 + 6H2O
Combustion (excess) Heat
Oxygen CO and H2O 2C2H6 + 5O2 4CO + 6H2O
(limited)
Free radical r.t.p. Ultraviolet Halogenoalkanes C2H6 Cl2 C2H5Cl + HCl
substitution light C2H5Cl + Cl2 C2H4Cl2 +
HCl
Reactions of Alkenes
Type of reaction reagents Conditions Main products Example
Steam 300℃ Alcohol C2H2 + H2O C2H5OH
ethane ethanol
Electrophilic conc H3PO4 60 atm
addition Hydrogen r.t.p. Halogenoalkane C2H4 +HCl C2H5Cl
chloroethane
halide
Halogen r.t.p. Halogenoalkane C2H4 + Cl2 CH2Cl-CH2Cl
1,2-dichloroethane
Catalytic addition Hydrogen 140 ℃ Alkane C2H4 + H2 C2H6
ethane
Nickel cat.
Alkaline r.t.p Alcohol (diol) C2H4 + [O] + H2O
Oxidation dil. KMnO4 CH2OH-CH2OH
ethan-1,2-diol
Alkaline Heat Ketones CH3
conc. Carboxylic acids
KMnO4 C CH CH CH2 + 7[O]
4,4-dimethyl 1,3-diene
CH3
CH3 O O
C O + C C
CH3 OH OH
propanone ethanedioic acid (oxalic acid)
Addition Monomers Heat Polymer n(C2H4) (C2H4)n
ethene polythene
polymerization + Pressure
Catalyst
Reactions of Arenes
Benzene
Type of reaction reagents Conditions Main products Example
Electrophilic Halogen + r.t.p. Halogenobenzene C6H6 +Br2 C6H5Br + HBr
benzene bromobenzene
substitution FeX3/Fe
(Halogenation)
Electrophilic conc HNO3 Reflux Nitrobenzene C6H6 + HNO3 C6H5NO2 + H2O
nitrobenzene
substitution conc H2SO4 below 60℃
(Nitration)
M. Kole
2
Elimination Haloalkane r.t.p. Alkylbenzene C6H6 + CH3Cl C6H5CH3 +HCl
methylbenzene
(Friedel-Crafts) AlCl3 cat
Methylbenzene
Type of reaction reagents Conditions Main products Example
Electrophilic Halogen r.t.p. Halogeno- 2C6H5CH3 + 2Br2 2C6H4(Br)CH3 +
2 2-bromomethylbenzene + 4-bromomethylbenzene
substitution methylbenzene
(Halogenation) 2H2O
Electrophilic conc. HNO3 30 ℃ nitromethylbenzene 2C6H5CH3 + 2HNO3 2C6H4(NO2)CH3 +
2-nitromethylbenzene + 4-nitromethylbenzene
substitution conc.H2SO4
(Nitration)
Free radical Halogen r.t.p. Halogenoarene C6H5CH3 + Cl2 C6H5CH2Cl +HCl
substitution uv light C6H5CH2Cl + Cl2 C6H5CHCl2 + HCl
dil. r.t.p. Aldehyde C6H5CH3 + 2[O] C6H5CHO + H2O
Oxidation acidified
KMnO4
dil. Heat Carboxylic acid C6H5CH3 + 3[O] C6H5COOH + H2O
acidified
KMnO4
Reactions of Halogenoalkanes
Type of reaction reagents Conditions Main products Example
Nucleophilic H2O Boil Alcohol C2H5Cl + NaOH C2H5OH + NaOH
chloroethane ethanol
substitution NaOH (aq)
(Hydrolysis)
Nucleophilic KCN in Reflux Nitrile CH3CH2I + KCN CH3CH2CN + KI
iodoethane propanenitrile
substitution alcohol
(formation of
nitrile)
Nucleophilic Excess Heat Amine CH3CH2Br + NH3 CH3CH2NH2 + HBr
bromoethane ethanamine
substitution conc. NH3
(formation of
amine)
Elimination NaOH in Boil Alkene CH3CH2Br + NaOH CH2=CH2 + HBr
ethene
alcohol
-
Test for NaOH Boil with Silver halide CH3CH2Br + OH CH3CH2OH + Br-
ethanol
halogenoalkane HNO3 NaOH, add
AgNO3 HNO3 then Ag+(aq) + Br-(aq) AgBr (s)
silver bromide
AgNO3
AgCl (white) AgBr (cream) AgI (yellow)
M. Kole
3
Reactions of hydroxyl compounds
Alcohols
Type of reaction reagents Conditions Main products Example
Combustion Oxygen Heat CO2 , H2O CH3CH2OH + 3O2 2CO2 + 3H2O
Hydrogen Heat in Halogenoalkane CH3CH2OH + HBr CH3CH2Br + H2O
ethanol bromoethane
Nucleophilic halide (HX) conc.
substitution (from NaX H3PO4
(with halide) + H2SO4)
Phosphorus r.t.p. Halogenoalkane 3CH3CH2OH + PI3 3CH3CH2I + H3PO3
iodoethane
halide (PX)
Displacement Sodium r.t.p. Sodium alkoxide CH3CH2OH + Na CH3CH2ONa + 1/2H2
Oxidation K2Cr2O7/H+ Reflux Aldehyde CH3CH2OH + [O] CH3CHO +H2O
ethanal
(primary
alcohol)
Type of reaction reagents Conditions Main products Example
Oxidation K2Cr2O7/H+ Reflux Ketone CH3CH(OH)CH3 + [O] CH3COCH3 +
propan-2-ol propanone
(secondary
alcohol) H2O
Elimination conc. 170 ℃ Alkene CH3CH2OH CH2=CH2 + H2O
ethanol ethene
(dehydration) H2SO4 cat.
or Al2O3 cat. Heat
Elimination/ Carboxylic Heat Ester CH3CH2OH + CH3COOH
ethanol ethanoic acid
Condensation acid
(esterification) conc. CH3COOCH2CH3 + H2O
ethylethanoate
H2SO4 cat.
Phenols
Type of reaction reagents Conditions Main products Example
Displacement Sodium r.t.p Sodium phenoxide C6H5OH +Na C6H5O-Na+
phenol sodium phenoxide
metal
Elimination Acyl r.t.p. Ester CH3COCl + C6H5OH H3COOC6H5
ethanoyl chloride phenylethanoate
(acylation) chloride
+ HCl
Neutralization Base r.t.p Metal ethoxide C6H5OH + NaOH C6H5O-Na+ + H2O
Electrophilic Bromine, r.t.p. 2,4,6- C6H5OH + 3Br2 C6H2Br3OH + 3HBr
substitution Br2 tribromophenol
(bromination)
Electrophilic Nitric acid, r.t.p. Nitrophenol C6H5OH + 2HNO3 C6H5OH +
substitution HNO3 2C6H4OHNO2
2-nitrophenol and 4-nitrophenol
(nitration)
M. Kole
4
Reactions of carboxylic acids
Type of reaction reagents Conditions Main products Example
Base Salt and water CH3COOH + NaOH CH3COONa + H2O
ethanoic acid sodium ethanoate water
Neutralization r.t.p.
Carbonate Salt and carbon CH3COOH + NaCO3 CH3COONa + CO2
dioxide
Displacement Sodium r.t.p. Salt and hydrogen CH3COOH + Na CH3COONa + 1/2H2
metal
Elimination/
condensation See alcohols
(esterification)
Formation of PCl5 Heat CH3COOH + PCl5 CH3COCl + POCl3
acyl chlorides Acyl chloride + HCl phosphorus pentachloride ethanoyl chloride
PCl3 Heat CH3COOH + PCl3 CH3COCl + H3PO4
SOCl2 r.t.p. CH3COOH + SOCl2 CH3COCl + SO2
+ HCl
Reactions of acyl chlorides
Type of reaction reagents Conditions Main products Example
Hydrolysis Water, H2O r.t.p. Carboxylic acid CH3COCl + H2O CH3COOH + HCl
Elimination Alcohol r.t.p. Ester CH3COCl + CH3CH2OH
(esterification) CH3COOCH2CH3 + HCl
ethyl ethanoate
Phenol in r.t.p. Ester CH3COCl + C6H5OH CH3COOC6H5 +
phenylethanoate
alkaline HCl
solution
Reactions of carbonyl compounds
Aldehydes
Type of reagents Conditions Main products Example
reaction
Nucleophilic HCN from KCN r.t.p Hydroxynitrile CH3CHO + HCN CH3CH(OH)CN
ethanal 2-hydroxypropanenitrile
addition + H2SO4 in
NaOH(aq)
NaBH4 in NaOH Warm
Reduction (aq) Primary alcohol CH3CHO + 2[H] CH3CH2OH
LiAlH4 in dry r.t.p.
ether
Addition- 2,4-dinitro r.t.p. 2,4-dinitrophenyl C6H3NO2NO2NH2 + CH3CHO
2,4-dinitrophenylhydrazine
elimination phenylhydranine hydrazone
(orange ppt) C6H3NO2NO2NH-NCHCH3 + H2O
2,4-dinitrophenylhydrazone
Tollen’s r.t.p. Silver (mirror) CH3CHO +2[Ag(NH3)2]+ + 3OH-
reagent, CH3COO- + Ag + 4NH3 + 2H2O
Oxidation 2[Ag(NH3)2]+(aq)
Fehling’s Warm Copper (I) oxide CH3CHO + 2Cu2+ + 5OH-
reagent Cu2+(aq)/ C2O (s) CH3COO- + Cu2O + 3H2O
OH-(aq) (brick-red ppt)
M. Kole
5
Triiodomethane Iodine in NaOH r.t.p. Triiodomethane, CH3CHO + 3I2 + 4NaOH
test/iodoform (aq) CHI3 (yellow ppt) CHOO-Na+ + CHI3 + 3NaI + 3H2O
triiodomethane
test
Oxidation Acidified Warm Carboxylic acid CH3CHO + [O] CH3COOH
2- 3+
K2Cr2O7 orange Cr2O7 turns green Cr
Ketones
Type of reagents Conditions Main products Example
reaction
Nucleophilic HCN from r.t.p. Hydroxynitrile CH3COCH3 + HCN
propanone
addition NaCN + H2SO4
in NaOH (aq) CH3C(OH)(CN)CH3
2-hydroxybutan-2-nitrile
NaBH4 in NaOH Warm CH3COCH3 + 2[H] CH3CH(OH)CH3
propan-2-ol
Reduction (aq) Secondary alcohol
LiAlH4 in dry r.t.p.
ether
Addition- 2,4-dinitro r.t.p. 2,4-dinitrophenyl C6H3NO2NO2NH2 + CH3COCH3
elimination phenylhydrazine hydrazine C6H3NO2NO2NH-NC(OH)CH3 + H2O
(orange ppt)
Triiodomethane Iodine in NaOH r.t.p. Triiodomethane, CH3CH2COCH3 + 3I2 + 4NaOH
butanone
test/iodoform (aq) CHI3 (yellow ppt)
test CH3CH2COO-Na+ + CHI3 + 3NaI +
3H2O
Reactions of organic nitrogen compounds
Type of reagents Conditions Main products Example
reaction
Nucleophilic KCN in alcohol reflux nitrile CH3I + CN - CH3CN
ethanenitrile
substitution
(formation of
nitrile from
triiodomethane)
Reduction LiAlH4 in dry reflux Primary amine CH3CN + 4[H] CH3CH2NH2
ethylamine
ether
(formation of
amine from
nitrile)
Phenylamine
Type of reagents Conditions Main products Example
reaction
Electrophilic Bromine, Br2 (aq) r.t.p. Tribromophenyl- C6H5NH2 + 3Br2 (aq) C6H2Br3NH2
phenylamine tribromophenylamine
substitution amine
+ 3HBr (g)
Diazotization HNO2 from HCl Below 5℃ Diazonium salt C6H5NH2 + HCl C6H5N2+Cl- +
benzenediazonium chloride
+ NaNO3 H2O
M. Kole
6
Diazonium salt
Type of reagents Conditions Main products Example
reaction
Hydrolysis Water, H2O Warm Phenol C6H5N2+Cl- + H2O C6H5OH + N2
phenol
+ HCl
Electrophilic Phenol in Below 5℃ Azodye C6H5N2+ + C6H5OH
substitution- NaOH(aq) (ice bath) C6H5N=NC6H4OH + H+
4-hydroxyphenylazobenzene (orange dye)
elimination
(coupling)
Amine
Type of reagents Conditions Main products Example
reaction
Nucleophilic Acyl chloride r.t.p. Amide CH3COCl + NH3 CH3CONH2
ethanoyl chloride ethanamide
substitution-
elimination
Amide
Type of reagents Conditions Main products Example
reaction
Hydrolysis Dilute acid/H2O Carboxylic acid CH3CONH2 + H2O CH3COOH +
ethanoic acid
(of amides) Boil NH3
Dilute alkali Acid salt CH3CONH2 + NaOH CH3COO-Na+
sodium ethanoate
+ NH3
Hydrolysis Dilute acid/H2O Carboxylic acid CH3CONHCH3 + H2O
methylethanamide
(of substituted and amine
amides) Boil CH3COOH + CH3NH2
methylamine
Dilute alkali Acid salt and CH3CONHCH3 + NaOH
amine CH3COO--Na+ + CH3NH2
Polymers
Type of reagents Conditions Main products Example
reaction
Addition Monomers Heat, plymer n(CH2=CH2) (CH2=CH2)n
ethene monomers polythene polymer
polymerisation moderate
pressure, n(CH2=CHC6H5) (CH2=CHC6H5)n
phenylethene monomers polyphenylethene
catalyst
Diamine + dioic Heat Polyamide n[H2N(CH2)6NH2+ HOOC(CH2)COOH]
1,6-diaminohexane hexane-1,6-dioic acid
acid in conc
Condensation H2SO4 [-HN(CH2)6NHOC(CH2)CO-]n
nylon-6,6
polymerization
(elimination) Diamine + acyl r.t.p Polyamide n[H2N(CH2)6NH2 + ClOCCOCl]
chloride [-HN(CH2)6NHOC(CH2)CO-]n
Diol + dioic Conc. Polyester n[HO(CH2)2OH + HOOCC6H4COOH]
ethanediol benzenedicarboxylic acid
acid H2SO4
[-O(CH2)2OOCC6H4CO-]n
terylene
M. Kole
