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Chapter 15: Q32P (page 712)

Problem:Propose a mechanism for the following reaction. (Hint: Number the carbons to help you see where they end up in the product.)

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01

Acid-catalyzed ester formation

Alcohol reacted with acids to form the ester using acid as a catalyze.

Methanol reacted with acetic acid in the presence of acid catalyze forms methyl acetate (ester) as shown below.

Formation of methyl acetate

02

Mechanism of ester formation

In the first step, protonation occurs on the double first carbon, resulting in the formation of the most stable tertiary carbocation.

In the second step, the pair of electrons from the second pie bonds provides the nucleophile that adds to the carbocation. As a result of this reaction, a stable six-membered ring formed with the ester functional group, forming the desired given ester.

The formation of the ester is shown below.

Mechanism of ester formation

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Most popular questions from this chapter

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

Question: What product do you expect to obtain from each of the following reactions?

a.

b.

When a compound with molecular formula C11H14O2undergoes acid-catalyzed hydrolysis, one of the products that is isolated gives the following H1NMR spectrum. Identify the compound.

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?

Two products, A and B, are obtained from the reaction of 1-bromobutane with NH3 . Compound A reacts with acetyl chloride to form C, and compound B reacts with acetyl chloride to form D. The IR spectra of C and D are shown. Identify A, B, C, and D.
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