Organic reactions

Part 1
 Organic reactions
•Combustion/ •Elimination reactions
Oxidation •Substitution reactions
•Esterification •Cracking:
•Addition reactions •Thermal
•Catalytic
Important
•You need to be able to identify:
• reactants
• products
• reaction conditions
•Structural formulae
•IUPAC - naming
Esterification
Acid-catalyzed condensation
Reactants: Alcohols and carboxylic acids

H H O
H C C O H + H O C H
H H

Ethanol Methanoic acid

Esterification

H H O
H C C O H + H O C H
H H

Ethanol Methanoic acid

Esterification
Products: Ester and water

H H O
H C C O C H + H O
H
H H

Ethyl methanoate
(Ethanol) (Methanoic acid)
 Addition reactions
H H
B C
A A + B C àH A A H
H H
H H

Unsaturated compound à Saturated compound

 Addition reaction
(Hydrogenation)
H2(g) + alkene moves over catalyst.
The process is used to make margarine from
plant oils.
H H
H H Pt
C C + H2 H C C H
H H
H H
ethene ethane
 Addition reaction
(Hydrogenation)
Reaction conditions:
Alkene dissolved in non-polar solvent
Catalyst: Pt, Ni, Pd
H H
H H Pt
C C + H2 H C C H
H H
H H
ethene ethane
 Addition reaction
(Halogenation)
Bubble a halogen through an alkene

Br H
H H
C C + Br2 H C C H
H H
H Br

ethene 1,2-dibromoethane
 Addition reaction
(Halogenation)

Reaction conditions:
Absence of water! NO water!

ethene 1,2-dibromoethane
Addition reaction
(Hydrohalogenation)
Bubble a hydrogen halide through an alkene.

H H
H H
C C + HBr H C C H
H H
H Br

ethene bromoethane
 Addition reaction
(Hydrohalogenation) Markovnikov’s
Reaction conditions: rule will apply!
Absence of water! NO water!
H H
H H
C C + HBr H C C H
H H
H Br

ethene bromoethane
 Addition reaction
(Markovnikov’s rule)
The carbon with the most hydrogens will get another hydrogen.
(Main product)

H Br
H H
C C + HBr H C C H
H
H C H HH C H
H H
propene 2-bromopropane
 Addition reaction Markovnikov’s
(Hydration) rule will apply!
Industry – preparation of alcohols. H2PO4 is used as catalyst

HO H
H H H3PO4
C C + O H C C H
H H H H
H H
ethene ethanol
 Addition reaction
(Hydration)
Reaction conditions:
Catalyst: Strong, dilute acid
Heat in form of steam HO H
H H H3PO4
C C + O H C C H
H H H H
H H
ethene ethanol
Elimination reaction
Saturated compound à Unsaturated compound
e.g. Ethanol moved across a hot catalyst

H O H
H H
H C C H C C + O
H H H H
H H
ethanol ethene
Zaitzev’s rule Elimination reaction
The carbon next to the hydroxyl with the least amount of
hydrogens will lose a hydrogen to form a double bond
(Main product) H O H H
H C C H H C C H + O
H H
HH C H HH C
H C H H C H
H H
Butan-2-ol But-2-ene
 Elimination reaction Zaitzev’s
(Dehydrohalogenation) rule will apply!
Reaction conditions:
Concentrated NaOH or KOH in ethanol as solvent; strong heat
H H
H H
H C C H + NaOH Hot
ethanolic C C + HBr
H H
H Br
bromoethane ethene
Elimination reaction
(Dehydration) Reaction conditions:
Zaitzev’s Catalyst: Strong conc acid in
rule will apply! excess; heating of alcohol
H O H
H3PO4 H H
H C C H C C + O
Heat
H H H H
H H
ethanol ethene
Elimination reaction
(Cracking)
Thermal cracking
Catalytic cracking
Saturated compound is cracked to produce an unsaturated
compound H H
Pt H H
H C C H heat C C + H2
H H
H H
ethane ethene
Substitution reaction
Halogenation (e.g. Alkanes)
A-B + C à A-C + B

H H
∆ or hf
H C H + Cl Cl H C H + H Cl
H Cl
Methane Chlorine Chloromethane
Substitution reaction
Hydrohalogenation (e.g. Tertiary alcohols)

H H
H C H H C H
H H
H C C OH + HBr H C C Br + H2O
H H
H C H H C H
H H
Tertiary alcohol Halo-alkane
Substitution reaction
Hydrolysis (e.g. Halo-alkanes)

H H H H
ethanol
H C C H + KOH H H + KBr
heat
C C
H Br H OH