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Chemistry

Chemistry · Aldehydes and Ketones

Work through this past-paper style MCQ, then read the full explanation. Practice more chemistry questions on mMCQ with adaptive drills and topic analytics.

Question

During reduction of aldehydes with NaBH4, which of the following intermediate is formed?

Options
  • A

    Carbanion

  • B

    Carbocation

  • C

    Carbene

  • D

    Alkoxide ion

Explanation

When aldehydes are reduced using NaBH4, the key intermediate formed is an alkoxide ion. The hydride ion (H-) from NaBH4 attacks the electrophilic carbonyl carbon of the aldehyde, forming an alkoxide intermediate. This intermediate is then protonated to yield the corresponding alcohol.

The other options are incorrect:

Carbanions are not involved as the mechanism does not require electron pair donation to carbon.

Carbocations are not formed because the reaction conditions do not favor the generation of positively charged carbon species.

Carbenes are not relevant as they do not participate in hydride transfer reactions.

A carbanion is a negatively charged carbon atom with extra electrons. In the reduction of aldehydes with NaBH4, a carbanion is not formed because the reaction mechanism involves hydride ion transfer rather than electron pair shifts that form carbanions.

A carbocation is a positively charged carbon atom with an incomplete octet. The reduction of aldehydes with NaBH4 does not involve the formation of carbocations, as the BH4- ion acts as a hydride donor, not an acid that would generate such species.

A carbene is a neutral species with a divalent carbon atom. Carbenes are not formed during the reduction of aldehydes with NaBH4, as the reaction involves hydride transfer rather than the creation of divalent carbon intermediates.

The BH4- ion from NaBH4 donates a hydride ion to the carbonyl carbon of the aldehyde, resulting in the formation of an alkoxide intermediate. This species is characterized by a negatively charged oxygen that is later protonated to form the corresponding alcohol.

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