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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

Unlike a phosphonium ylide that reacts with an aldehyde or a ketone to form an alkene, a sulfonium ylide reacts with an aldehyde or a ketone to form an epoxide. Explain why one ylide forms an alkene, whereas the other forms an epoxide.

What amides would you react with LiAlH4 to form the following amines?

a. benzylmethylamine c. diethylamine

b. ethylamine d. triethylamine

Question:a.What would have been the product of the preceeding reaction with LiAlH4 if the keto group had not been protected?

b. What reagent could you use to reduce only the keto group?

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?

What are the products of the following reactions?
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