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

Bruice8th EditionOrganic ChemistryISBN: 9780135213711당신이 사용하는 게 아니라요?교과서 변경

Bruice 8th Edition

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

문제 16

16장, 문제 16

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

검증된 단계별 안내

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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이 영상 해법은 위 문제에 도움이 된다고 튜터들이 추천한 것입니다.

영상 길이:

주요 개념

질문에 올바르게 답하기 위해 반드시 이해해야 하는 핵심 개념들은 다음과 같습니다.

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.