Asked in PMC Practice Test 10 (2021) 2021Moderate

When a nucleophilic reagent attacks on alcohols, what happens?

Correct answer: A. C - O bond breaks

  • A. C - O bond breaks
  • B. H bond breaks
  • C. Increase in acidity
  • D. Dehydration occurs

Explanation

Option A: When a nucleophilic reagent attacks an alcohol, the nucleophile interacts with the carbon atom in the alcohol molecule. This interaction leads to the breaking of the carbon-oxygen (C-O) bond in the alcohol. The nucleophile replaces the oxygen atom, resulting in the formation of a new compound with the nucleophile bonded to the carbon atom, while the leaving group, typically an oxygen-containing fragment, departs from the molecule. This process is known as nucleophilic substitution, where the C-O bond in the alcohol is broken and a new bond is formed with the nucleophile.Option B: H bond breaks: In the context of nucleophilic attack on alcohols, the breaking of hydrogen (H) bonds is less likely to occur. Nucleophilic reagents typically target the carbon atom of the alcohol rather than the hydrogen atom.Option C: Increase in acidity: Nucleophilic attack on an alcohol does not typically result in an increase in acidity. Acidity refers to the ability of a compound to donate a proton (H+), and nucleophilic attack involves the donation or sharing of electron pairs by the nucleophile with the carbon atom of the alcohol.Option D: Dehydration occurs: Dehydration refers to the removal of a water molecule from a compound. When a nucleophilic reagent attacks an alcohol, it can lead to the elimination of a water molecule, resulting in the formation of a new compound with the loss of water. This process often involves the use of a strong acid or a strong dehydrating agent.

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About Alcohols

Alcohols contain a hydroxyl group attached to a saturated carbon atom and are classified as primary, secondary or tertiary. Their nomenclature, hydrogen bonding, acidity, oxidation, dehydration, reaction with sodium and conversion to haloalkanes are covered, along with the distinction between alcohols and phenols, where the hydroxyl group is attached directly to an aromatic ring.

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