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Question 47

The major products A and B in the following set of reactions are:

The starting material in this reaction sequence is a cyanohydrin (specifically, acetone cyanohydrin). To form major product A, the reactant is treated with lithium aluminum hydride (LiAlH₄) followed by acidic workup. LiAlH₄ is a strong reducing agent that specifically targets the nitrile group (-CN) and reduces it to a primary amine (-CH₂NH₂). Because it does not react with tertiary alcohols, the hydroxyl group (-OH) remains completely intact, resulting in an amino alcohol for product A. To form major product B, the reactant is subjected to strongly acidic conditions using hydronium ions and sulfuric acid (H₃O⁺ / H₂SO₄). This triggers two consecutive reactions. First, the acid completely hydrolyzes the nitrile group (-CN) into a carboxylic acid group (-COOH). Immediately following this, the strong dehydrating nature of sulfuric acid causes the elimination of the tertiary hydroxyl group (-OH) along with a hydrogen from an adjacent methyl group. This dehydration forms a stable, conjugated carbon-carbon double bond, yielding an alpha, beta-unsaturated carboxylic acid as product B.

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