A student wanted to synthesize 4-(5-methylhex-3-yn-1-yl)phenol. The student's key step was to be the Sn2 reaction of an acetylide with 4-(2-bromoethyl)phenol. However, the student isolated none of the desired product. What went wrong? Draw the two products the student isolated instead. Assume a 1:1 mixture of reagents. Br 4-(2-bromoethyl)phenol HO HO :c=C- 4-(5-methylhex-3-yn-1-yl)phenol acetylide Draw the two products the student isolated instead. Select Draw Rings More Erase H Br

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
Chapter18: Functional Derivatives Of Carboxylic Acids
Section: Chapter Questions
Problem 18.70P
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A student wanted to synthesize 4-(5-methylhex-3-yn-1-yl)phenol. The student's key step was to be the SN2 reaction of an
acetylide with 4-(2-bromoethyl)phenol. However, the student isolated none of the desired product. What went wrong?
Draw the two products the student isolated instead. Assume a 1:1 mixture of reagents.
Br
4-(2-bromoethyl)phenol
но
HO
:c=C-
4-(5-methylhex-3-yn-1-yl)phenol
acetylide
Draw the two products the student isolated instead.
Select
Draw
Rings
More
Erase
C
H
Br
Transcribed Image Text:A student wanted to synthesize 4-(5-methylhex-3-yn-1-yl)phenol. The student's key step was to be the SN2 reaction of an acetylide with 4-(2-bromoethyl)phenol. However, the student isolated none of the desired product. What went wrong? Draw the two products the student isolated instead. Assume a 1:1 mixture of reagents. Br 4-(2-bromoethyl)phenol но HO :c=C- 4-(5-methylhex-3-yn-1-yl)phenol acetylide Draw the two products the student isolated instead. Select Draw Rings More Erase C H Br
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