The two alkenes shown below were synthesized from alkynes. Identify the alkyl br

Question

The two alkenes shown below were synthesized from alkynes. Identify the alkyl bromides that were reacted with acetylene to form the alkyne, and the method of alkyne reduction.

A)

1. The alkyl bromide used for alkylation of the 'left' side (as drawn) of acetylene:

2. The alkyl bromide used for alkylation of the 'right' side (as drawn) of acetylene:

3. The method of alkyne reduction:

B)

1. The alkyl bromide used for alkylation of the 'left' side (as drawn) of acetylene:

2. The alkyl bromide used for alkylation of the 'right' side (as drawn) of acetylene:

3. The method of alkyne reduction:

a. CH3(CH2)6CH2Br b. CH3(CH2)11CH2Br c. CH3(CH2)3CH2Br d. (CH3)2CHCH2Br e. CH3CH2CH(CH3)CH2CH2Br

Explanation / Answer

Solution :-

A)

1. The alkyl bromide used for alkylation of the 'left' side (as drawn) of acetylene

Solution :- Answer is option D that is (CH3)2CHCH2Br

2. The alkyl bromide used for alkylation of the 'right' side (as drawn) of acetylene:

Solution :- Answer is option c. that is CH3(CH2)3CH2Br

3. The method of alkyne reduction:

Solution :- Li/NH3 is used to reduce the convert the alkyne triple bond to the trans alkene.

B)

1. The alkyl bromide used for alkylation of the 'left' side (as drawn) of acetylene

Solution :- answer is option d. that is (CH3)2CHCH2Br

2. The alkyl bromide used for alkylation of the 'right' side (as drawn) of acetylene:

Solution :- answer is option c. that is CH3(CH2)3CH2Br

3. The method of alkyne reduction:

Solution :- H2/Lindlars is used to reduce the alkyne triple bond to the cis alkene.

The alkyl halides are selected by looking at the number of the carbons in the chain on each side of the alkene structures.

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