Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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**Reduction of a Ketone Using Sodium Borodeuteride (NaBD₄) in Ethanol (EtOH)**

*Chemical Reaction:*

The following image illustrates a two-step chemical reaction process for the reduction of a ketone functional group. 

1. The reactant is a ketone compound. In this specific case, the structure displays a four-carbon chain with a ketone group (C=O) attached to the second carbon atom.
  
2. The first step of the reaction involves the addition of Sodium Borodeuteride (NaBD₄) in Ethanol (EtOH). Sodium Borodeuteride is a deuterated reducing agent often used to convert ketones into alcohols.
  
3. The second step involves the addition of an aqueous acidic workup (H₃O⁺), which is essential to neutralize the reaction mixture and to protonate the intermediate product to finally yield the corresponding alcohol.

**Structure Description:**

- The structure on the left shows a ketone (a carbon double-bonded to an oxygen atom, C=O) attached to a secondary carbon (R-C-R1 configuration).
- The reducing agent is specified as NaBD₄, indicating deuterium (D) is used instead of hydrogen (H).
- The reaction conditions include ethanol (EtOH) as the solvent.
- The protonation step is indicated by H₃O⁺ (hydronium ion).

**Explanation:**

Ketones are typically reduced to secondary alcohols. Initially, the deuterated borohydride (NaBD₄) donates a deuteride (D⁻) ion to the carbonyl carbon of the ketone. This reduction step results in the formation of an alkoxide intermediate. This intermediate is then protonated (H⁺) during the acidic workup to yield the final alcohol product, where the carbonyl oxygen is replaced with a hydroxyl group (OH) and the hydrogen at the formerly carbonyl carbon is replaced with deuterium (resulting from NaBD₄).

This reaction is commonly used in organic chemistry laboratories to introduce deuterium into molecules for tracing studies or pharmacokinetic profiling due to the presence of deuterium.
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Transcribed Image Text:**Reduction of a Ketone Using Sodium Borodeuteride (NaBD₄) in Ethanol (EtOH)** *Chemical Reaction:* The following image illustrates a two-step chemical reaction process for the reduction of a ketone functional group. 1. The reactant is a ketone compound. In this specific case, the structure displays a four-carbon chain with a ketone group (C=O) attached to the second carbon atom. 2. The first step of the reaction involves the addition of Sodium Borodeuteride (NaBD₄) in Ethanol (EtOH). Sodium Borodeuteride is a deuterated reducing agent often used to convert ketones into alcohols. 3. The second step involves the addition of an aqueous acidic workup (H₃O⁺), which is essential to neutralize the reaction mixture and to protonate the intermediate product to finally yield the corresponding alcohol. **Structure Description:** - The structure on the left shows a ketone (a carbon double-bonded to an oxygen atom, C=O) attached to a secondary carbon (R-C-R1 configuration). - The reducing agent is specified as NaBD₄, indicating deuterium (D) is used instead of hydrogen (H). - The reaction conditions include ethanol (EtOH) as the solvent. - The protonation step is indicated by H₃O⁺ (hydronium ion). **Explanation:** Ketones are typically reduced to secondary alcohols. Initially, the deuterated borohydride (NaBD₄) donates a deuteride (D⁻) ion to the carbonyl carbon of the ketone. This reduction step results in the formation of an alkoxide intermediate. This intermediate is then protonated (H⁺) during the acidic workup to yield the final alcohol product, where the carbonyl oxygen is replaced with a hydroxyl group (OH) and the hydrogen at the formerly carbonyl carbon is replaced with deuterium (resulting from NaBD₄). This reaction is commonly used in organic chemistry laboratories to introduce deuterium into molecules for tracing studies or pharmacokinetic profiling due to the presence of deuterium.
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