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Chapter 9: Q9-10 Pa (page 278)

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

a.CH3CH2CH2C鈮�CH

Short Answer

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Answer

Method

1. a.CH3CH2CH2C鈮�CH+CH3Br鈫�CH3CH2CH2C鈮�CCH3

2.a.CH3C鈮�CH+CH3CH2CH2Br鈫�CH3CH2CH2C鈮�CCH3

Step by step solution

01

Alkylation

Migration of the alkyl group from one molecule to another via carbanion or carbocation formation

02

Alkylation of acetylide ion

Acetylide ion is a strong nucleophile that reacts with the electrophile like alkyl halide that replaces the halide and forms alkyne. Hence new C-C bond is formed, and the old C-Br bond is broken.

03

Illustration of the second mechanism

The attack of alkyne acts as a nucleophile and leads to the formation of a transition state, and the removal of halogen takes place.

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Most popular questions from this chapter

What products would you obtain by hydration of the following alkynes?

How would you carry out the following reactions to introduce deuterium into organic molecules?

(a)

b.

c.

d.

Each of the following syntheses requires more than one step. How

would you carry them out?

(a)

(b)

Using any alkyne needed, how would you prepare the following alkenes?

(c) 3-Methyl-1-pentene

Terminal alkynes react with and water to yield bromo ketones. For example:

Propose a mechanism for the reaction. To what reaction of alkenes is

the process analogous?
See all solutions

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