Cyanohydrin formation is useful because of the further chemistry that can be carried out on

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
Chapter23: Amines
Section: Chapter Questions
Problem 23.57P
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(a) Cyanohydrin formation is useful because of the further chemistry that can be carried out on
the product. A nitrile can be reduced to yield a primary amine and also hydrolyzed to yield
a carboxylic acid. Thus, cyanohydrin formation provides a method of transforming an
aldehyde or ketone into a different functional group. Identify a series of synthetic
transformation of the following reaction starting with benzaldehyde:
(iii)
(v)
(i)
H.
(vi)
(iv)
(b) Treatment of an aldehyde or ketone with cyanide ion (:C=N), followed by protonation of
the tetrahedral alkoxide ion intermediate, gives a cyanohydrin. Show the structure of the
cyanohydrin obtained from cyclohexanone, with mechanistic explanation.
HCN
Transcribed Image Text:(a) Cyanohydrin formation is useful because of the further chemistry that can be carried out on the product. A nitrile can be reduced to yield a primary amine and also hydrolyzed to yield a carboxylic acid. Thus, cyanohydrin formation provides a method of transforming an aldehyde or ketone into a different functional group. Identify a series of synthetic transformation of the following reaction starting with benzaldehyde: (iii) (v) (i) H. (vi) (iv) (b) Treatment of an aldehyde or ketone with cyanide ion (:C=N), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin. Show the structure of the cyanohydrin obtained from cyclohexanone, with mechanistic explanation. HCN
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