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NEETChemistryAldehydes and Ketones

Consider the reaction of methyl 2-(2-oxopropyl)benzoate with NaBH ₄ , followed by heating with concentrated H ₂ SO ₄ . What is the major organic product formed?

Options

  1. A1-(Prop-1-en-1-yl)-2-vinylbenzene
  2. BMethyl 2-allylbenzoate
  3. CMethyl 2-(2-hydroxypropyl)benzoate
  4. DMethyl 2-(prop-1-en-1-yl)benzoate

Correct answer

D. Methyl 2-(prop-1-en-1-yl)benzoate

Step-by-step solution

NaBH ₄ is a mild reducing agent. It exhibits chemoselectivity by reducing the ketone group in the 2-oxopropyl side chain to a secondary alcohol, but it does not reduce the ester group. The intermediate formed is methyl 2-(2-hydroxypropyl)benzoate. Heating with concentrated H ₂ SO ₄ leads to the acid-catalyzed dehydration of the secondary alcohol. Dehydration can yield two possible alkenes. According to Zaitsev's rule and thermodynamic stability, the double bond forms in conjugation with the aromatic ring rather tha

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