Why is the following reaction sequence not an efficient approach to the desired product?4-CEC-H2)1) NaNH23) NANH24) CH3BRCEC-Br(NOT produced)O NANH2 is used in the reduction of alkynes to trans alkenesO Br is not a good enough leaving groupO The secondary alkyl halide could undergo an elimination reactionO The terminal alkyne is not acidic enough to be deprotonated

terminal alkynes contains acidic hydrogens eg: acetylene (ethyne), 1-propyne etc this acidic H…

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Why is the following reaction sequence not an efficient approach to the desired product?

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.50P

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Concept explainers

Alkynes

Alkynes are organic compounds that contain at least one triple bond between carbon-carbon atoms. They are a series of unsaturated compounds with a general molecular formula, CnH2n-2.

Question

Why is the following reaction sequence not an efficient approach to the desired product?
4-CEC-H
2)
1) NaNH2
3) NANH2
4) CH3BR
CEC-
Br
(NOT produced)
O NANH2 is used in the reduction of alkynes to trans alkenes
O Br is not a good enough leaving group
O The secondary alkyl halide could undergo an elimination reaction
O The terminal alkyne is not acidic enough to be deprotonated

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