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2-Bromopropane reacts with Mg in dry ether to give a product which on treatment with HCHO forms an addition product. The addition product on hydrolysis forms

  • A.1-butanol
  • B.2-butanol
  • C.2-propanol
  • D.2-methyl-1-propanol
  • E.2-methyl-2-propanol

Answer: D

The final product is 2-methyl-1-propanol.

2-Bromopropane and magnesium give the Grignard reagent (CH3)2CHMgBr. It adds to formaldehyde (HCHO), and hydrolysis of the adduct gives a primary alcohol with one more carbon:

(CH3)2CH-MgBr + HCHO → (CH3)2CH-CH2OMgBr → (CH3)2CH-CH2OH

(CH3)2CHCH2OH is 2-methyl-1-propanol. Formaldehyde always gives a primary alcohol, which rules out the secondary and tertiary alcohols; 1-butanol has a straight chain, but the isopropyl group keeps the branch.

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