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Chapter 16: Q14P (page 750)

What is the product of the reaction of an ester with excess acetylide ion followed by the addition of pyridinium chloride?

Short Answer

Expert verified

The product is tertiary alcohol.

Step by step solution

01

Reaction of acetylide ion with ester

When ester is reacted with acetylide ion, it forms a ketone first.This is a type of nucleophilic addition-elimination reaction.

02

Step 2: Addition of pyridinium chloride

After the nucleophilic addition-elimination reaction, the ketone is then converted to a tertiary alcohol finally. This is a process of nucleophilic addition reaction. The complete reaction is given below:

Addition of pyridinium chloride

03

Use of pyridinium chloride in nucleophilic addition reaction

Pyridinium chloride helps in protonating the alkoxide ion. HCl or H3O+ is not used instead of pyridinium chloride because they cannot form triple bonds.

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Most popular questions from this chapter

  1. Propose a mechanism for the following reaction:
  2. What is the product of the following reaction?

Rank the following compounds from most reactive to least reactive toward nucleophilic addition:

a. Would you expect hemiacetals to be stable in basic solutions? Explain your answer.

b. Acetal formation must be catalyzed by an acid. Explain why it cannot be catalyzed by CH3O-

c. Can the rate of hydrate formation be increased by hydroxide ion as well as by acid? Explain.

a. Write the mechanism for the following reactions:

1. the acid-catalyzed hydrolysis of an imine to a carbonyl compound and a primary amine

2. the acid-catalyzed hydrolysis of an enamine to a carbonyl compound and a secondary amine

b. How do the two mechanisms differ?

Question:Using bromocyclohexane as a starting material, how could you synthesize the following compounds?
See all solutions

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