Which product forms when an aldehyde is oxidized by silver oxide?

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Multiple Choice

Which product forms when an aldehyde is oxidized by silver oxide?

Explanation:
Oxidizing an aldehyde with silver oxide follows the idea behind Tollens’ test: aldehydes are readily oxidized further to a carboxyl-containing product. In the basic, ammonia-containing solution, the aldehyde loses electrons to become a carboxylate (RCOO−) while Ag+ in Ag2O is reduced to metallic silver. After an acid workup, the carboxylate is converted to the carboxylic acid (RCOOH). That’s why the product is a carboxylic acid. This reagent isn’t set up to produce an alcohol or an ester from an aldehyde, and it doesn’t preserve the aldehyde as-is, so those options don’t fit. The key point is that the aldehyde is oxidized one more step to a carboxyl group under this oxidizing condition.

Oxidizing an aldehyde with silver oxide follows the idea behind Tollens’ test: aldehydes are readily oxidized further to a carboxyl-containing product. In the basic, ammonia-containing solution, the aldehyde loses electrons to become a carboxylate (RCOO−) while Ag+ in Ag2O is reduced to metallic silver. After an acid workup, the carboxylate is converted to the carboxylic acid (RCOOH). That’s why the product is a carboxylic acid.

This reagent isn’t set up to produce an alcohol or an ester from an aldehyde, and it doesn’t preserve the aldehyde as-is, so those options don’t fit. The key point is that the aldehyde is oxidized one more step to a carboxyl group under this oxidizing condition.

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