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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

Draw the structure for each of the following:

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

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

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?

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

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

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
See all solutions

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