Single correct option
Propanoic acid is treated successively with (i) / red , then ; (ii) excess ; (iii) / dilute at . The final organic product, as actually obtained, is
- A. 2-hydroxypropanoic acid, a single optically active enantiomer
- B. 2-hydroxypropanoic acid, a racemic (optically inactive) mixture
- C. 3-hydroxypropanoic acid, optically inactive
- D. propenoic acid, optically inactive
Show answer and solution
Answer: (B) 2-hydroxypropanoic acid, a racemic (optically inactive) mixture
(i) Hell-Volhard-Zelinsky bromination replaces an -hydrogen: . (ii) Nucleophilic substitution by excess gives 2-aminopropanoic acid (alanine). (iii) The primary amino group on the aliphatic -carbon reacts with nitrous acid to give a diazonium salt that is displaced by water, forming 2-hydroxypropanoic (lactic) acid with loss of . The -carbon is a stereocentre, but the HVZ step is not stereoselective and the later steps do not create a single enantiomer from an achiral precursor, so the product is racemic and optically inactive.
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