Mechanism Of Electrophilic Substitution Reactions

Hydrocarbon of Class 12

1.Nitration:

(i) Formation of electrophile Mechanism Of Electrophilic Substitution Reactions

Mechanism Of Electrophilic Substitution Reactions

(base)     (acid)    (nitronium ion)

(ii) Electrophilic attack by Mechanism Of Electrophilic Substitution Reactions

Mechanism Of Electrophilic Substitution Reactions

In the intermediate, attacked carbon atom changes its state of hybridization from trigonal to tetrahedral.

Mechanism Of Electrophilic Substitution Reactions

(iii) Loss of proton :

Mechanism Of Electrophilic Substitution Reactions

2. Friedel – Craft Alkylation:

This reaction involves the introduction of alkyl group into benzene ring in presence of catalyst. The alkylating agent may be R – X, ROH or alkene. The catalyst is a Lewis acid, Mechanism Of Electrophilic Substitution Reactions

Mechanism Of Electrophilic Substitution Reactions

Mechanism:

Step I: Formation of electrophile (carbonium ion) stability order of carbonium ion is

Mechanism Of Electrophilic Substitution Reactions

 With ROH:

Mechanism Of Electrophilic Substitution Reactions

With alkene :

Mechanism Of Electrophilic Substitution Reactions

Step II :

Mechanism Of Electrophilic Substitution Reactions

Step III :

Mechanism Of Electrophilic Substitution Reactions

Examples:

Mechanism Of Electrophilic Substitution Reactions

 

or Mechanism Of Electrophilic Substitution Reactionscarbonium ion.

This is an example of intermolecular Friedel Craft alkylation. But if the side chain contains four or five carbons with halogen at the end then it may undergo intramolecular Friedel – Craft reaction.

Mechanism Of Electrophilic Substitution Reactions

3.Friedel – Craft Acylation:

Replacement of Mechanism Of Electrophilic Substitution Reactions of benzene by Mechanism Of Electrophilic Substitution Reactions group using carboxylic acid, esters, acid chloride or acid anhydride as acylating agent in the presence of Lewis acid.

Mechanism Of Electrophilic Substitution Reactions

Mechanism:

Mechanism Of Electrophilic Substitution Reactions

(II) is more stable than (I) because each atom has a complete octet.

 

Examples:

Mechanism Of Electrophilic Substitution Reactions

Reactions of side chains

1.Halogenation:

Mechanism Of Electrophilic Substitution Reactions

WithMechanism Of Electrophilic Substitution Reactionsin presence of Mechanism Of Electrophilic Substitution Reactionsundergoes electrophilic substitution at o- and p- position and in the absence of Mechanism Of Electrophilic Substitution Reactions and in the presence of light or high temperature undergoes substitution in the side chain (free radical substitution).

Mechanism Of Electrophilic Substitution Reactions

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