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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

The reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, does not work with primary alcohols.

a. Propose a mechanism for the Ritter reaction.

b. Why does the Ritter reaction not work with primary alcohols?

c. How does the Ritter reaction differ from the acid-catalyzed hydrolysis of a nitrile to form an amide?

a. What is the product of the reaction of acetyl chloride withHO-? ThepKaof HCl is -7; thepKaofH2Ois 15.7.

b. What is the product of the reaction of acetamide withHO-? ThepKaofNH3is 36; thepKaofH2Ois 15.7.

Draw the structure for each of the following:

\(\begin{array}{}a.{\rm{ phenyl acetate}}\\b.{\rm{ }}\gamma {\rm{ - caprolactam}}\\c.{\rm{ sodium formate}}\\d.{\rm{ N - benzylethanamide}}\\e.{\rm{ }}\gamma {\rm{ - methylcaproic acid}}\\f.{\rm{ }}\beta {\rm{ - bromobutyramide}}\\g.{\rm{ ethyl 2 - chloropentanoate}}\\h.{\rm{cyclohexanecarbonyl chloride}}\\i.{\rm{ }}\alpha {\rm{ - chlorovaleric acid}}\\\end{array}\)

If propionyl chloride is added to one equivalent of methylamine, only a 50% yield of N-methylpropanamide is obtained. If, however, the acyl chloride is added to two equivalents of methylamine, the yield of N-methylpropanamide is almost 100%. Explain these observations.

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