How to prepare the following substance from an alkyl halide through an SN2 reaction.

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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How to prepare the following substance from an alkyl halide through an SN2 reaction.
 
 
 
 
 
 
 
H-C=C-CH2CH,CH3
Transcribed Image Text:H-C=C-CH2CH,CH3
Expert Solution
Step 1

We can form terminal alkyne through E² elimination reaction.

Explanation: 

First of all we should know these concepts: 

1) in E¹ elimination reaction there should be a good leaving group. After removal of leaving group carbocation is generated and then hydrogen is taken out by base. So it is unimolecular reaction.

2) in E² elimination reaction both leaving group that is carbon-halogen and carbon-hydrogen  break at a time which occurs in one step mechanism and form C=C (pi bond).

But Here there is possibility of formation of saytzeff product and hoffman product.

But if we take bulky base or less concentrate base then Hoffman product will be major product and less hindered proton will remove

If we take less bulky base or concentrated base then more hindered site proton will remove and hoffman product will be majore product.

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