Summary of Organic Reactions (III.

Aromatic hydrocarbons)

Page 1

III.
A. 1.

Aromatic hydrocarbons
Substitution reactions of benzene Nitration
NO2
conc. HNO3(aq) conc. H2SO4(l) 55°C benzene

nitrobenzene

Note :

No reaction if conc. H2SO4(l) is not added.
X

2.

Halogenation
X
2

FeX3 or AlX3 benzene halobenzene

3.

Sulphonation
O O S O H
conc. H2SO4

heat benzene benzenesulphonic acid O O S O H NaOH(s) 350°C benzenesulphonic acid O Na
+

H3O

+

OH

sodium phenoxide / sodium phenolate

phenol

Note : Industrial preparation of phenol

4.

Alkylation
R RX and AlX3

benzene

alkylbenzene

B.

Oxidation of alkylbenzene
O R 1) KMnO4, OH , heat 2) H3O alkylbenzene
+ -

C OH

benzenecarboxylic acid

2. A.Summary of Organic Reactions (IV. 1. Reaction with potassium cyanide KCN(aq) R X haloalkane R CN nitrile 3. Halogeno-compounds) Page 6 IV. Reaction with ammonia H N H +R X H ammonia haloalkane H N R +R X H 1° amine haloalkane R N R +R X H 2° amine haloalkane H N R H 1° amine N + HX R R + HX H 2° amine R N R + HX R 3° amine R - R N R R 3° amine +R X R N RX haloalkane R quaternary ammonium halide Note : A mixture of products would be obtained. 4. Reaction with alkoxide R X + R' O Na haloalkane sodium alkoxide + R O R' ether 5. Reaction with carboxylate ion O R X + R' C O Na sodium haloalkane carboxylate + O R' C O R ester . Halogeno-compounds Nucleophilic substitution Reaction with sodium hydroxide R X haloalkane X NaOH(aq) heat halobenzene phenol NaOH(aq) R OH alcohol OH Note : Prolonged heating is required for the alkaline hydrolysis of halobenzene.

1. Halogeno-compounds) B.) R C C R R R haloalkane R R alkene 2. Elimination reaction Reaction with alcoholic sodium hydroxide to form alkene X R C Page 7 H C R NaOH(alc. Reaction with alcoholic sodium hydroxide to form alkyne X R C X C R boiling NaOH(alc.Summary of Organic Reactions (IV.) R C C R H H 1.2-dihaloalkane alkyne .