Carbonyl Attack

Carbonyl attack is a fundamental organic chemistry process in which a nucleophile forms a bond to the electrophilic carbon of a carbonyl group. The reaction occurs because the polarized carbon-oxygen bond gives the carbon partial positive character; as the nucleophile approaches, the carbonyl pi bond shifts toward oxygen, producing a tetrahedral intermediate that can undergo proton transfer or elimination. This mechanism underlies nucleophilic addition to aldehydes and ketones and nucleophilic acyl substitution in carboxylic acid derivatives. Understanding carbonyl attack helps explain reactions used to synthesize alcohols, amides, esters, and other important compounds in laboratory research and industrial chemistry.

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Education

JoVE Core - Civil Engineering

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Research

JoVE Journal - Chemistry

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2025

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction. Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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