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.
$a . {CH}_{3} {CH}_{2} {CH}_{2} C \equiv CH$

Short Answer

Expert verified

Answer

Method

1. $a . {CH}_{3} {CH}_{2} {CH}_{2} C \equiv CH + {CH}_{3} Br \to {CH}_{3} {CH}_{2} {CH}_{2} C \equiv {CCH}_{3}$

2. $a . {CH}_{3} C \equiv CH + {CH}_{3} {CH}_{2} {CH}_{2} Br \to {CH}_{3} {CH}_{2} {CH}_{2} C \equiv {CCH}_{3}$

Step by step solution

Alkylation

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

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.

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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Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.
$a . {CH}_{3} {CH}_{2} {CH}_{2} C \equiv CH$

Short Answer

Step by step solution

Alkylation

Alkylation of acetylide ion

Illustration of the second mechanism

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Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.a.CH3CH2CH2C≡CH

Short Answer

Step by step solution

Alkylation

Alkylation of acetylide ion

Illustration of the second mechanism

One App. One Place for Learning.

Most popular questions from this chapter

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Nuclear Chemistry

Chemical Reactions

The Earths Atmosphere

Organic Chemistry

Making Measurements

Study anywhere. Anytime. Across all devices.

Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.
$a . {CH}_{3} {CH}_{2} {CH}_{2} C \equiv CH$