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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

Why, in the last step of the mechanism for hydroxide-ion promoted hydrolysis of an amide, is the amide ion protonated?

When butanoic acid and 18O-labelled methanol react under acidic conditions, what compounds are labelled when the reaction has reached equilibrium?

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?

We saw that acid anhydrides react with alcohols, water, and amines. In which of these reactions can the tetrahedral intermediate eliminate the carboxylate ion even if it does not lose a proton before the elimination step? Explain.

When treated with an equivalent of methanol, compound A, with the molecular formula C4H6Cl2O, forms the compound whose 1H NMR spectrum is shown here. Identify compound A.
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