1. CH3CH,Br + CH3CH,SH NH2 2. HO, H20 H2N NH2 ethanethiol НAN thiourea urea

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
Chapter17: Carboxylic Acids
Section: Chapter Questions
Problem 17.45P
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Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.

a. Propose a mechanism for the reaction.

b. What thiol will be formed if the alkyl halide employed is pentyl bromide?

1. CH3CH,Br
+ CH3CH,SH
NH2 2. HO, H20
H2N
NH2
ethanethiol
НAN
thiourea
urea
Transcribed Image Text:1. CH3CH,Br + CH3CH,SH NH2 2. HO, H20 H2N NH2 ethanethiol НAN thiourea urea
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