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The Cannizaro Reaction

Cyclohexanone...

Question

Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethytcyclohexanone does not. Explain why ?

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Solution

Cyclohexanes form cyanohydrins according to the following equation, as refer to the IMAGE $01$ .
In this case, the nucleophile $C N^{-}$ can easily attack with out any steric hindrance. However, in case of $2, 2, 6 - t r i - m e t h y l - c y c l o - h e x a n o n e$ , metyl groups at $α -$ position offer steric hindrance, as a result $C ⊝ N$ group cannot attack effectively.
As refer to IMAGE $02$ . For this reason, it does not form a cyanohydrin.

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Similar questions

Q. Give a plausible explanation for the following.

Cyclohexanone forms cyanohydrins in good yield but

2, 2, 6

- trimethyl cyclohexanone does not.

Q. Give plausible explanation for each of the following:
(i) Cyclohexanone forms cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not.
(ii) There are two

N H_{2}

groups in semicarbazide. However, only one is involved in the formation of semicarbazones.
(iii) During the preparation of esters from a carboxylic acid and an alcohol in the presence of an acid catalyst, the water or the ester should be removed as soon as it is formed.

Q. Consider the following statements
(i) Out of two

- N H_{2}

groups in semicarbazide only one is involved in formation of semicarbazones.
(ii) Cyclohexane froms cyanohydrin in good yield but

2, 2, 6 - t r i m e t h y l c y c l o h e x a n o n e

does not.
(iii) The

α - h y d r o g e n s

in aldehydes and ketones are acidic.

Q. (a) Give a possible explanation for each one of the following:
(i) There are two

- N H_{2}

, groups in semicarbazide. However, only one such group is involved in the formation of semicarbazones.
(ii) Cyclohexanone forms cyanohydrin in good yield but 2, 4, 6-trimethylcyclohexanone does not.
(b) An organic compound with molecular formula

C_{9} H_{10} O

forms 2, 4, -DNP derivative, reduces Tollens' reagent and undergoes Cannizzaro's reaction. On vigorous oxidation it gives 1, 2-benzene-di-carboxylic acid. Identify the compound?

Q. A carbonyl compound does not reduce Tollen's reagent or Fehling's solution but gives a positive iodoform test. It forms a cyanohydrin with

H C N

. The compound is:

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