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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鈥檚 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

Which alkyl halides form the carboxylic acids listed hereafter reaction with sodium cyanide followed by heating the product in an acidic aqueous solution?

a. butyric acid

b. isovaleric acid

c. cyclohexane carboxylic acid

Two products, A and B, are obtained from the reaction of 1-bromobutane with NH3 . Compound A reacts with acetyl chloride to form C, and compound B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.

What alkyl bromide would you use in a Gabriel synthesis to prepare each of the following amines?

  1. Pentylamine

  2. Iso hexyl amine

  3. Benzylamine

  4. Cyclohexylamine

Name the following.

How could you use 1H NMR spectroscopy to distinguish the following esters?
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