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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

a. Which of the following reactions does not give the carbonyl product shown?

b. Which of the reactions that do not occur can be made to occur if an acid catalyst is added to the reaction mixture?

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

Name the following:

a. Propose a mechanism for the formation of succinic anhydride in the presence of acetic anhydride.

b. How does acetic anhydride make it easier to form the anhydride?

a. What species other than an acid can be used to increase the rate of the transesterification reaction that converts methyl acetate to propylacetate?

b. Explain why the rate of aminolysis of an ester cannot be increased by H+, HO-, or RO-.
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