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 20c,d

Chapter 17, Problem 20c,d

What alcohols are obtained from the reduction of the following compounds with sodium borohydride?
c. 4-tert-butylcyclohexanone
d. acetophenone

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Identify the functional group in each compound. For 4-tert-butylcyclohexanone, the functional group is a ketone (C=O) attached to a cyclohexane ring with a tert-butyl group at the 4-position. For acetophenone, the functional group is also a ketone (C=O) attached to a benzene ring with a methyl group on the carbonyl carbon.

Understand the role of sodium borohydride (NaBH₄). Sodium borohydride is a reducing agent that selectively reduces ketones and aldehydes to their corresponding alcohols. It donates a hydride ion (H⁻) to the carbonyl carbon, converting the C=O bond into a C-OH bond.

For 4-tert-butylcyclohexanone, the reduction will occur at the ketone group. The hydride ion from NaBH₄ will attack the carbonyl carbon, breaking the double bond and forming a secondary alcohol. The tert-butyl group remains unchanged.

For acetophenone, the reduction will also occur at the ketone group. The hydride ion will attack the carbonyl carbon, converting the ketone into a secondary alcohol. The benzene ring and the methyl group remain unchanged.

After the reduction, the products are alcohols. For 4-tert-butylcyclohexanone, the product is 4-tert-butylcyclohexanol. For acetophenone, the product is 1-phenylethanol. These alcohols are formed as a result of the reduction of the ketone groups in the original compounds.

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Key Concepts

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

Reduction Reactions

Reduction reactions involve the gain of electrons or hydrogen, or the loss of oxygen in a chemical species. In organic chemistry, this often refers to the conversion of carbonyl compounds (like ketones and aldehydes) into alcohols. Sodium borohydride (NaBH4) is a common reducing agent used for this purpose, as it selectively reduces ketones and aldehydes to their corresponding alcohols.

Sodium Borohydride

Sodium borohydride is a powerful and selective reducing agent commonly used in organic synthesis. It is particularly effective for reducing ketones and aldehydes to alcohols without affecting other functional groups. Its mild nature allows for the reduction of sensitive compounds, making it a preferred choice in laboratory settings for producing alcohols from carbonyl precursors.

Structure of Alcohols

Alcohols are organic compounds characterized by the presence of one or more hydroxyl (-OH) groups attached to a carbon atom. The structure of the starting carbonyl compound influences the structure of the resulting alcohol. For example, the reduction of 4-tert-butylcyclohexanone will yield a tertiary alcohol, while the reduction of acetophenone will yield a secondary alcohol, reflecting the different carbon environments in these compounds.

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