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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

Question: Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.

a.Propose a mechanism for the reaction.

b.What thiol will be formed if the alkyl halide employed is pentyl bromide?

Question: Fill in the boxes:

Identify compounds A and B:

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.

Show how the following compounds can be synthesized from cyclohexanol.

a.

b.

c.
See all solutions

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