Consider the data below to answer the following questions. Cyanohydrins are important intermediates in the synthesis of a-hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. HO H HCEN H-3- HO' NaOH HO cyanohychin a. a nucleophilic substitution b. an electrophilic addition C10 OH CH-COOH A. The reaction of an aldehyde with hydrogen cyanide is an example of + NaCN + H₂O reaction. H- C. an electrophilic substitution d. a nucleophilic addition B. Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.

Chemistry for Today: General, Organic, and Biochemistry
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Chapter16: Amines And Amides
Section: Chapter Questions
Problem 16.54E
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Consider the data below to answer the following questions.
Cyanohydrins are important intermediates in the synthesis of a-hydroxycarboxylic acids from ketones
and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic
acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a
cyanohydrin is treated with aqueous base the original carbonyl compound is isolated.
HO
H
HCEN
H-3-
HO'
NaOH
HO
cyanohychin
a.
a nucleophilic substitution
b.
an electrophilic addition
C10
OH
CH-COOH
A. The reaction of an aldehyde with hydrogen cyanide is an example of
+ NaCN + H₂O
reaction.
H-
C.
an electrophilic substitution
d. a nucleophilic addition
B. Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.
Transcribed Image Text:Consider the data below to answer the following questions. Cyanohydrins are important intermediates in the synthesis of a-hydroxycarboxylic acids from ketones and aldehydes. The nitrile functional group can be hydrolyzed by aqueous acid to yield a carboxylic acid. Nitriles can also be hydrolyzed to carboxylic acids using aqueous base. Unfortunately, when a cyanohydrin is treated with aqueous base the original carbonyl compound is isolated. HO H HCEN H-3- HO' NaOH HO cyanohychin a. a nucleophilic substitution b. an electrophilic addition C10 OH CH-COOH A. The reaction of an aldehyde with hydrogen cyanide is an example of + NaCN + H₂O reaction. H- C. an electrophilic substitution d. a nucleophilic addition B. Identify the electrophile in the reaction of benzaldehyde with hydrogen cyanide.
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