Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook

Bruice 8th Edition

Ch. 16 - Reactions of Aldehydes and Ketones • More Reactions of Carboxylic Acid Derivatives

Problem 16

Chapter 17, Problem 16

Can a cyanohydrin be prepared by treating a ketone with sodium cyanide?

Verified step by step guidance

Identify the functional groups involved: A cyanohydrin is formed from a ketone or aldehyde and contains a hydroxyl group (-OH) and a cyano group (-CN) attached to the same carbon.

Understand the reaction mechanism: The reaction involves nucleophilic addition of the cyanide ion (CN⁻) to the carbonyl carbon of the ketone.

Consider the role of sodium cyanide: Sodium cyanide (NaCN) provides the cyanide ion (CN⁻) necessary for the nucleophilic attack on the carbonyl carbon.

Recognize the conditions required: The reaction typically occurs in the presence of an acid, such as HCl, to protonate the oxygen and stabilize the intermediate, leading to the formation of the cyanohydrin.

Conclude the feasibility: Yes, a cyanohydrin can be prepared by treating a ketone with sodium cyanide under the appropriate acidic conditions.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Cyanohydrin Formation

Cyanohydrins are organic compounds formed when a carbonyl compound, such as an aldehyde or ketone, reacts with hydrogen cyanide (HCN) or a cyanide salt. This reaction involves the nucleophilic addition of the cyanide ion to the carbonyl carbon, leading to the formation of a hydroxyl group and a cyano group on the same carbon atom.

Nucleophilic Addition

Nucleophilic addition is a fundamental reaction mechanism in organic chemistry where a nucleophile attacks an electrophilic carbon atom, typically found in carbonyl groups. In the case of cyanohydrin formation, the cyanide ion acts as the nucleophile, attacking the electrophilic carbon of the ketone, resulting in the formation of a new carbon-carbon bond.

Role of Sodium Cyanide

Sodium cyanide (NaCN) is a source of cyanide ions in organic reactions. When treating a ketone with sodium cyanide, the cyanide ion generated can effectively participate in nucleophilic addition to the carbonyl group of the ketone, facilitating the formation of a cyanohydrin. This reaction is significant in organic synthesis for introducing functional groups into molecules.

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Related Practice

Textbook Question

Show how the following compounds can be prepared, using ethyne as one of the starting materials:

2. 1-phenyl-2-butyn-1-ol

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Textbook Question

What alcohols are obtained from the reduction of the following compounds with sodium borohydride?

c. 4-tert-butylcyclohexanone

d. acetophenone

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Textbook Question

What products are obtained from the reaction of the following compounds with LiAlH₄ followed by treatment with dilute acid?

a. ethyl butanoate

b. benzoic acid

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Textbook Question

Explain why ethyne should be alkylated before, rather than after, nucleophilic addition.

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Textbook Question

What is the product of the reaction of an ester with excess acetylide ion followed by the addition of pyridinium chloride?

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Textbook Question

What alcohols are obtained from the reduction of the following compounds with sodium borohydride?

a. 2-methylpropanal

b. cyclohexanone

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