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Chapter 18: Q15P (page 942)

Propose a mechanism for each cyanohydrin synthesis just shown.

Short Answer

Expert verified

The conjugate base of hydrogen cyanide (HCN) is cyanide ion (CN-) . Cyanide ion is considered to be a strong base as well as a strong nucleophile also. Cynaide ion can attack carbonyl compounds (aldehydes and ketones) to form an additional product which is more commonly known as the cyanohydrins

Step by step solution

01

Cyanohydrins

The conjugate base of hydrogen cyanide (HCN) is cyanide ion (CN-) . Cyanide ion is considered to be a strong base as well as a strong nucleophile also. Cynaide ion can attack carbonyl compounds (aldehydes and ketones) to form an additional product which is more commonly known as the cyanohydrins

02

Mechansim for the synthesis of each cyanohydrin

The formation of cyanohydrin is a type of base-catalyzed addition to a carbonyl group where a strong nucleophile (CN-) adds in the first step to give an alkoxide which on protonation in the second step forms the cyanohydrin.

(propanol) (propanol cyanohydrin)

(butane-2-one) (butane-2-one cyanohydrin)

(di-tert-butylketone)

Ketones hindered by the presence of large alkyl groups usually react very slowly with hydrogen cyanide and give poor yields of cyanohydrins. Poor yield is due to steric effects.

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Most popular questions from this chapter

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or asymmetrical alkynes. Show what products would be from hydration fo each compound.

(a) hex-3-yne

(b) hex-2-yne

(c) hex-1-yne

(d) cyclodecyne

(e) 3-methylcyclodecyne

For each compound,

  1. Name the functional group,
  2. Show what compounds result from complete hydrolysis.

Propose mechanisms for

(a) the acid-catalyzed hydration of chloral to form chloral hydrate.

(b) the base-catalyzed hydration of acetone to form acetone hydrate

In the absence of water, ophthalaldehyde has the structure shown. Its strong IR absorption is at 1687 cm-1; the proton NMR data are shown by the structure. In the presence of water, a new compound is formed that has a strong IR absorption around 3400 cm-1 and no absortion in the C=0 region. propose a structure of X consistent with this information and suggest how X consistent with this information and suggest how X was formed.

Propose a mechanism for the acid-catalyzed reaction of benzaldehyde with methanol to give benzaldehyde dimethyl acetal.
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