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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

Expert verified

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 group $R - C = O$ 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 ${NO}_{2}$ group, while compound D consists of an electron-donating methoxy $- {OCH}_{3}$ 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

Draw the product formed when the $α, β$ -unsaturated ketone A is treated with each reagent.

(a) NaBH₄, CH₃OH

(b) H₂ (1 equiv), Pd-C

(c) H₂ (excess), Pd-C

(d) [1] CH₃Li ; [2]H₂O

(e) [1] CH₃CH₂MgBr ; [2]H₂O

(f) [1] ${({CH}_{2} = {CH}_{2})}_{2}$ ; [2]H₂O

What product is formed when each compound is treated with either Ag₂O, NH₄OH or Na₂Cr₂O₇, H₂SO₄, H₂O?

Draw two different ways to prepare each ketone from an acid chloride and an organocuprate reagent.

a.

b.

Question: Fenofibric is a cholesterol-lowering medication that is converted to fenofibric acid, the active drug, by hydrolysis during metabolism. What is the structure of fenofibric acid?

Question: What product is formed when acetic acid is treated with each reagent: (a) ${CH}_{3} {NH}_{2}$ ; (b) ${CH}_{3} {NH}_{2}$ , then heat; (c) ${CH}_{3} {NH}_{2}$ + DCC?

See all solutions

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