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Chapter 11: Problem 37

Acetone on reduction with \(\mathrm{NaBH}_{4}\) gives 2 -Propanol.

Short Answer

Expert verified
Answer: The product formed in the reduction of acetone with sodium borohydride is 2-propanol. The basic mechanism of this reaction involves a nucleophilic attack by a hydride ion (H-) from NaBH4 on the electrophilic carbon of the carbonyl group in acetone, followed by hydrogen abstraction to form 2-propanol.

Step by step solution

01

Identify the reactants

We have two reactants in this reaction: 1. Acetone (CH3)2CO: A carbonyl compound, in which a carbonyl group is flanked by two methyl groups. 2. Sodium borohydride (NaBH4): A commonly used reducing agent in organic chemistry.
02

Understand the role of the reducing agent

Sodium borohydride (NaBH4) is a selective reducing agent that is used to reduce ketones and aldehydes into alcohols. NaBH4 specifically reduces the carbonyl group (C=O) to an alcohol group (C-O-H).
03

Write the reaction equation

Write the balanced chemical equation for the reduction of acetone to 2-propanol: (CH3)2CO + NaBH4 → (CH3)2CHOH + NaBO2 This equation shows acetone (CH3)2CO reacting with sodium borohydride (NaBH4) to produce 2-propanol ((CH3)2CHOH) and a sodium borate side product (NaBO2).
04

Understand the reaction mechanism

The reaction mechanism for the reduction of acetone by NaBH4 involves the following steps: 1. The hydrogen from NaBH4's hydride group (H-) acts as a nucleophile, attacking the electrophilic carbon atom of the carbonyl group in acetone. 2. This forms a new carbon-hydrogen bond, turning the carbonyl group into an alkoxide ion intermediate (-O-). 3. Finally, the oxygen of the alkoxide intermediate abstracts a hydrogen from water or an alcohol, resulting in the hydroxyl group (OH) and forming 2-propanol.
05

Describe the final product

2-Propanol (also known as isopropanol) is an alcohol with the chemical formula (CH3)2CHOH. It has a hydroxyl group (OH) attached to the second carbon atom in a three-carbon chain (propane). In summary, the given exercise involves the reduction of acetone with NaBH4 to produce 2-propanol through the process of nucleophilic attack and hydrogen abstraction.

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