JEE MainChemistryAlcohols Phenols and Ethers
Acetophenone is subjected to the following sequence of reactions: (i) CH₃MgBr , followed by H₃O^+ (ii) Conc. H₂SO₄ , (iii) B₂H₆ followed by H₂O₂ / OH^- (iv) Pyridinium chlorochromate (PCC) The major product formed at the end of the sequence is :
Options
- A2-Phenylpropanoic acid
- B1-Phenyl-1-propanone
- C2-Phenylpropanal
- D2-Phenyl-2-propanol
Correct answer
C. 2-Phenylpropanal
Step-by-step solution
Step 1: Acetophenone reacts with methylmagnesium bromide (Grignard reagent) followed by acidic workup to undergo nucleophilic addition, forming a tertiary alcohol, 2-phenyl-2-propanol. Step 2: Heating 2-phenyl-2-propanol with concentrated H₂SO₄ causes acid-catalyzed dehydration, yielding 2-phenylpropene as the major product. Step 3: Hydroboration-oxidation of 2-phenylpropene with B₂H₆ followed by H₂O₂ / OH^- results in anti-Markovnikov addition of water, producing the primary alcohol, 2-phenyl-1-propanol. Step 4: P