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Organic Chemistry and Analysis

The nucleophilic addition mechanism

  • 1 thing to know
  • Components 02 and 03

Overview

Recall questions on why the carbonyl carbon is electrophilic, the hydride and cyanide attacks, the intermediate formed, and the protonation that completes it.

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Process

What happens to the π bond during nucleophilic addition to a carbonyl, what intermediate forms, and which reagent detects a carbonyl group?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    In the mechanism of NaBH₄ reduction, what species acts as the nucleophile?

    Model answer

    The hydride ion (H⁻)

  2. 2

    Which atom does the hydride ion attack during the NaBH₄ reduction mechanism?

    Model answer

    The electrophilic carbonyl carbon

  3. 3

    After hydride attack in the NaBH₄ mechanism, what protonates the organic intermediate?

    Model answer

    Water

  4. 4

    In the HCN addition mechanism, which species performs the initial nucleophilic attack?

    Model answer

    The cyanide ion (CN⁻)

  5. 5

    Why does the cyanide ion attack the carbonyl carbon during HCN addition?

    Model answer

    Because the carbonyl carbon carries a partial positive charge (δ+), making it electrophilic

  6. 6

    In the HCN mechanism, what provides the proton in the subsequent protonation stage?

    Model answer

    H₂O or H⁺

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AThe first step is Cl• + O₃ → ClO• + O₂.
BThe second step is ClO• + O → Cl• + O₂.
CThe overall equation is O₃ + O → 2O₂.

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In ClO⁻, chlorine has oxidation number +1.
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