Paaras Thakur

Organic Chemistry

SNAr Mechanisms
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 Reactions of Haloarenes

Aryl halides are extremely less reactive towards nucleophilic substitution

reactions due to the following reasons:

1. Resonance effect
 Reactions of Haloarenes

2. Difference in hybridisation of carbon atom in C—X bond

Thus, C—Cl bond length in haloalkane is 177pm while in haloarene is 169 pm.
 Reactions of Haloarenes

3. Instability of phenyl cation:

Replacement by hydroxyl group
Replacement by hydroxyl group
 Aromatic Nucleophilic Substitution SNAr

EWG groups activate the ring towards SNAr

Addition - Elimination Mechanism

Elimination - Addition Mechanism

 Addition - Elimination Mechanism

Nucleophilic substitution reactions of aryl halides do occur readily when an

electronic factor makes the aryl carbon bonded to the halogen susceptible to
nucleophilic attack.

Nucleophilic aromatic substitution can occur when strong electron-withdrawing

groups are ortho or para to the halogen atom
 Addition - Elimination Mechanism

Mechanism
 Addition - Elimination Mechanism

Order of reactivity for Halogens is:

Addition - Elimination Mechanism
Example What is the product of the following reaction?
 Elimination - Addition or Benzyne Mechanism

Although aryl halides such as chlorobenzene and bromobenzene do not react

with most nucleophiles under ordinary circumstances, they do react under highly
forcing conditions.
 Elimination - Addition or Benzyne Mechanism

Mechanism
Elimination - Addition or Benzyne Mechanism

Unactivated benzene derivatives react via this mechanism.

Favored in presence of a strong base e.g. NaNH 2 or high Temp and Pressure

Alpha Hydrogen must be present.

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