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Chapter 15: Q44P (page 721)

Propose a mechanism for the reaction of an acyl chloride with acetate ion to form an acid anhydride

Short Answer

Expert verified

Mechanism followed as:

Step by step solution

01

Reaction of acyl chloride with acetate

It’s the reaction used for the formation of acidic anhydride on the reaction of the acyl chloride with sodium acetate followed by the removal of the sodium from sodium acetate and the chloride from acyl chloride the acetic anhydride formed.

02

Mechanism

Mechanism followed as:

  1. Removal of the sodium from the sodium acetate

  2. The acetate oxygen on reaction with acyl carbonyl so the electron density shifted to carbonyl oxygen having a negative charge.

  3. Again the electron density comes back from oxygen and again the carbonyl formation occurs and the leaving the chloride ion to occur

  4. Acetic anhydride formation occur

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Most popular questions from this chapter

Phosgene (COCl2) was used as a poison gas in World War I. What product would be formed from the reaction of phosgene with each of the following reagents?

a. one equivalent of methanol

b. excess methanol

c. excess propylamine

d. excess water

Problem:Propose a mechanism for the following reaction. (Hint: Number the carbons to help you see where they end up in the product.)

Problem: Which of the following reactions lead to the Formation of an amide?

Problem:What acyl chloride and amine are required to synthesize the following amides?

a. N-ethylbutanamide b. N,N-dimethylbenzamide

The aromas of many flowers and fruits are due to esters such as those shown in this problem. What are the common names of these esters? (Also see Problem 57.)
See all solutions

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