Write the stepwise mechanism of nucleophilic addition reactions in the carbonyl compounds.
Ans. Nucleophilic addition reactions in carbonyl compounds involve the attack of a nucleophile on the electrophilic carbon of the carbonyl group, resulting in the formation of a tetrahedral intermediate. Here’s a stepwise mechanism for nucleophilic addition reactions in carbonyl compounds, taking the example of an aldehyde or ketone:
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Nucleophilic Attack:
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The nucleophile (Nu:-) attacks the partially positive carbon atom of the carbonyl group.
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The nucleophile donates its electron pair to the electrophilic carbon, breaking the π bond between the carbon and oxygen.
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The electrons from the π bond move towards the oxygen atom, creating a negative charge on oxygen.
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Formation of Tetrahedral Intermediate:
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The attack of the nucleophile forms a tetrahedral intermediate.
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The carbon atom of the carbonyl group now has four substituents: the nucleophile (Nu:-), a hydrogen atom (in aldehydes), an alkyl group (in ketones), and the oxygen atom.
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The oxygen atom carries a negative charge.
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Proton Transfer (in some cases):
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In some cases, especially in the presence of acidic conditions, a proton transfer may occur.
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A proton from the solvent or another molecule is transferred to the oxygen atom.
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This results in the neutralization of the negative charge on oxygen and the formation of the final product.
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Deprotonation (in some cases):
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In basic conditions, deprotonation may occur instead of proton transfer.
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A proton from the solvent or the surrounding medium may abstract a proton from the resulting intermediate.
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This results in the formation of the final product with a negatively charged oxygen atom.
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Product Formation:
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The final step involves the collapse of the tetrahedral intermediate.
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The π bond between the carbon and oxygen reforms, expelling the leaving group (O: or H: depending on the conditions).
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The product of the nucleophilic addition reaction is formed, with the nucleophile attached to the former carbonyl carbon.
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