The number of compounds from the following which can undergo reaction with Br2/KOH (alcoholic) to give respective products and these respective products can also be obtained separately by Gabriel phthalimide reaction is : [figure]
- 5
- 4
- 3
- 6
Answer
(3) 3
Solution
Hofmann bromamide degradation works only for primary amides (R-CONH2) and gives R-NH2 (one carbon less). The N-substituted amides C6H11CONHCH2CH3 and (CH3)3CCONHCH3 do not react.
Products of the four primary amides:
C6H5CONH2 C6H5NH2 (aniline): ✗ by Gabriel — as per NCERT, aryl halides do not undergo nucleophilic substitution with the phthalimide anion
C6H5CH2CONH2 C6H5CH2NH2 (benzylamine): ✓ (from benzyl chloride)
CH3CONH2 CH3NH2 (methanamine): ✓ (from methyl halide)
C6H11CONH2 C6H11NH2 (cyclohexanamine): ✓ (from cyclohexyl halide)
∴ Number of compounds = 3
Answer: (3)