Question

Aryl halides do not undergo nucleophilic substitution
reactions under ordinary conditions because
1. approach of nucleophile is retarded
2. carbon carrying halogen atom is sp³ hybridised
3. the substrate molecule is destabilised due to resonance
4. partial double bond character between carbon and
halogen
(a) 2 and 4 only (b) 1 and 4 only
(c) 2 and 3 only (d) 2, 3 and 4 only

Answer 1

Answer:

Aryl halides do not undergo nucleophilic substitution

reactions under ordinary conditions because

1. approach of nucleophile is retarded

2. carbon carrying halogen atom is sp³ hybridised

3. the substrate molecule is destabilised due to resonance

4. partial double bond character between carbon and

halogen

(a) 2 and 4 only

(b) 1 and 4 only

(c) 2 and 3 only

(d) 2, 3 and 4 only

Answer 2

Option 1 and 4 are correct.

Explanation:

• In an aryl halide, the halogen atom has free lone pairs that can be donated in the benzene ring.

• This forms the partial double character of the state, and has stronger bond than a single bond.

• The aryl halide is attached to a carbon atom that is sp2 hybrid.

• The aryl halide, when the halogen group is lost, the positive charge of the benzene ring is much lessened by means of resonance.

• So the nucleophilic substitution isn't very fesable, because the approach of nucleophile gets stuck because of the partial positive charge in all the 6 carbon atoms.

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