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Chapter 15: Q79P (page 736)

Identify the major and minor products of the following reaction:

Short Answer

Expert verified

The carbonyl carbon of acid chloride is highly polar due to the electronegative groups connected to it. So the acyl chloride undergoes nucleophilic addition elimination reaction. A tetrahedral intermediate is produced in this reaction.

Step by step solution

01

Step-by-step-solutionStep 1: Reaction of acid chloride

The carbonyl carbon of acid chloride is highly polar due to the electronegative groups connected to it. So the acyl chloride undergoes nucleophilic addition elimination reaction. A tetrahedral intermediate is produced in this reaction.

02

Identifying the major and minor products of the reaction

The amine is a better nucleophile than the alcohol. The reactivity of acyl chloride makes it easily react with both nucleophiles. Hence, the steric hinderance is an important factor for determining the rate of formation of the products.

Major and minor products of the reaction

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Most popular questions from this chapter

Name the following:

a. Propose a mechanism for the reaction of acetic anhydride with water.

b. How does this mechanism differ from the mechanism for the reaction of acetic anhydride with an alcohol?

Which is longer, the carbon–oxygen single bond in a carboxylic acid or the carbon–oxygen bond in an alcohol? Why?

Which is a correct statement?

A. The delocalization energy of an ester is about 18 kcal/mol, and the delocalization energy of an amide is about 10 kcal/mol.

B. The delocalization energy of an ester is about 10 kcal/mol, and the delocalization energy of an amide is about 18 kcal/mol.

There are three carbon–oxygen bonds in methyl acetate.

a.What are their relative bond lengths?

b.What are the relative infrared (IR) stretching frequencies of these bonds?
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