Problem

Show how you would accomplish the following syntheses. (a) acetophenone acetophen...

Show how you would accomplish the following syntheses.

(a) acetophenone acetophenone cyanohydrin

(b) cyclopentanecarbaldehyde 2-cyclopentyl-2-hydroxyacetic acid

(c) hexan-1-ol 2-hydroxyheptanoic acid

Step-by-Step Solution

Solution 1

(a) Acetophenone cyanohydrins are formed by the reaction of acetophenone with liquid HCN with a catalytic amount of sodium cyanide.

Step #2 of 3

(b) Cyclopentanecarbaldehyde first reacts with HCN to given cyclopentanecarbaldehyde cyanohydrin which further reacts with aqueous acid to given 2-cyclopentyl-2-hydroxy acetic acid.

Step #3 of 3

(c ) First 1-hexanol is oxidized to 1-hexanal. 1-hexanal reacts with HCN to given

hexanal cyanohydrins which further reacts with aqueous acid to give 2-hydroxy

heptanoic acid.

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Solutions For Problems in Chapter 18

73SP
74SP

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