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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

An aqueous solution of a primary or secondary amine reacts with an acyl chloride to form an amide as the major product. However, if the amine is tertiary, an amide is not formed. What product isformed? Explain.

Catalytic antibodies catalyze a reaction by forcing the conformation of the substrate in the direction of the transition state. The synthesis of antibody is carried out in the presence of a transition state analog-a stable molecule that structurally resembles the transition state. This causes an antibody to be generated that recognizes and binds to the transition state, thereby stabilizing it. For example, the following transition state analog has been used to generate a catalytic antibody that catalyzes the hydrolysis of structurally similar ester:

a. Draw a possible transition state for the hydrolysis of the reaction.

b. The following transition state analog is used to generate a catalytic antibody for the catalysis of ester hydrolysis. Draw the structure of an ester whose rate of hydrolysis would be increased by this catalytic antibody.

c. Design a transition state analog that catalyzes amide hydrolysis at the amide group indicated.

The following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine CH2OH. Propose a mechanism to account for the inhibition and for the reactivation.

Name the following:

What reagent should be used to carry out the following reaction?
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