Q19-5P Treatment of an aldehyde or keto... [FREE SOLUTION]

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Chapter 19: Q19-5P (page 613)

Treatment of an aldehyde or ketone with cyanide ion ( ${}^{-}: C 鈮� N$ ), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin.
Show the structure of the cyanohydrin obtained from cyclohexanone.

Short Answer

Expert verified

Cyanohydrin formation occurs by adding 鈥渘ucleophile cyanide (CN)鈥� to the carbonyl carbon of aldehyde/ketone.

The formation of cyanohydrin leads to the following changes:

The formation of an alkoxide ion intermediate by pushing an electron pair from the C=O bond to the oxygen atom.
Carbonyl carbon hybridization change from ${sp}^{2} 鈫� {sp}^{3}$ .

Step by step solution

Step-by-Step SolutionStep 1:Formation of Cyanohydrin

Cyanohydrin formation occurs by adding 鈥渘ucleophile cyanide (CN)鈥� to the carbonyl carbon of aldehyde/ketone.

The formation of cyanohydrin leads to the following changes:

The formation of an alkoxide ion intermediate by pushing an electron pair from the C=O bond to the oxygen atom.
Carbonyl carbon hybridization change from ${sp}^{2} 鈫� {sp}^{3}$ .

Step 2:Structure of Cyanohydrin formed

The nucleophile addition of cyanide ion on the carbonyl carbon of cyclohexanone (ketone) occurs in the following steps:

Cyanide anion adds to the positively polarized carbon to form a tetrahedral intermediate.
This intermediate is protonated to yield the cyanohydrin.

The formation and structure of the cyanohydrin are shown as follows:

Structure of cyanohydrin formed

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91影视

Treatment of an aldehyde or ketone with cyanide ion ( ${}^{-}: C 鈮� N$ ), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin.
Show the structure of the cyanohydrin obtained from cyclohexanone.

Short Answer

Step by step solution

Step-by-Step SolutionStep 1:Formation of Cyanohydrin

Step 2:Structure of Cyanohydrin formed

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91影视

Treatment of an aldehyde or ketone with cyanide ion (:-C鈮�N), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin.Show the structure of the cyanohydrin obtained from cyclohexanone.

Short Answer

Step by step solution

Step-by-Step SolutionStep 1:Formation of Cyanohydrin

Step 2:Structure of Cyanohydrin formed

One App. One Place for Learning.

Most popular questions from this chapter

Recommended explanations on Chemistry Textbooks

Chemistry Branches

Ionic and Molecular Compounds

Chemical Analysis

Making Measurements

Physical Chemistry

Nuclear Chemistry

Study anywhere. Anytime. Across all devices.

Treatment of an aldehyde or ketone with cyanide ion ( ${}^{-}: C 鈮� N$ ), followed by protonation of the tetrahedral alkoxide ion intermediate, gives a cyanohydrin.
Show the structure of the cyanohydrin obtained from cyclohexanone.