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Chapter 22: Q39. (page 914)

Question: Which ester, C or D, is more reactive in nucleophilic acyl substitution? Explain your reasoning.

Short Answer

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Answer

Compound C is more reactive than compound D.

Step by step solution

01

Step-by-Step SolutionStep 1: Reactivity of esters towards nucleophilic acyl substitution

Nucleophilic acyl substitution reactions are the reactions between an acyl groupR-C=O and electron-rich species (nucleophile).

The compounds in which the carbonyl carbon of the acyl group is electron-deficient are more reactive towards nucleophilic substitution reactions.

02

Skeletal structures of the given compounds

The skeletal structures of compounds C and D are as follows:

Structure of compound C

Structure of compound D

03

Reactivity of compounds C and D

Compound C consists of an electron-withdrawing nitro NO2 group, while compound D consists of an electron-donating methoxy-OCH3 group.

The presence of an electron-withdrawing group (EWG) increases the reactivity of the ester towards nucleophilic acyl substitution.

Therefore, compound C is more reactive than compound D.

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Most popular questions from this chapter

Question: Without reading ahead in Chapter 22, state whether it should be possible to carry out each of the following nucleophilic substitution reactions.

a.

b.

c.

d.

Question: Draw the products of each reaction.

a.

b.

c.

Question: Draw the products of each reaction.

a.

b.

c.

d.

Explain why metal hydride reduction gives an endo alcohol as the major product in one reaction given below and an exo alcohol as the major product in the other reaction.

Question: Explain why imidazolides are much more reactive than other amides in nucleophilic acyl substitution.
See all solutions

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