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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

List three different sets of reagents (each set consisting of a carbonyl compound and a Grignard reagent) that could be used to prepare each of the following tertiary alcohols

a. In an aqueous solution, d-glucose exists in equilibrium with two six-membered ring compounds. Draw the structures of these compounds.

b. Which of the six-membered ring compounds will be the major product?

Question:Explain why aldehydes and ketones react with a weak acid such as hydrogen cyanide but do not react with strong acids such as HCl or H2SO4 (other than being protonated by them).

Question: Propose a mechanism for each of the following reactions:

Question: Show two ways to convert an alkyl halide into a carboxylic acid that has one more carbon than the alkyl halide.
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