A [(ii) H3O+](i) NaOH B [(ii) H2SO4, ](i) EtOH C 'A' shows positive Lassaigne's test for N and its molar mass is 121. 'B' gives effervescence with aq NaHCO3. 'C' gives fruity smell. Identify A, B and C from the following.
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Answer
(3) [figure]
Solution
'B' gives effervescence (CO2) with aq. NaHCO3 B is a carboxylic acid.
'C' (fruity smell) is an ester, formed from B by esterification with EtOH / conc. H2SO4.
'A' contains N, has molar mass 121 and gives the acid on hydrolysis with NaOH followed by H3O+ A is an amide.
Benzamide, C6H5CONH2: 7(12) + 7(1) + 14 + 16 = 121 ✓
C6H5CONH2 [(ii) H3O+](i) NaOH C6H5COOH [(ii) H2SO4, ](i) EtOH C6H5COOC2H5
(benzamide → benzoic acid → ethyl benzoate)
Other options: in (1) aminobenzaldehyde has no α-H (no aldol) and its products contain no –COOH; in (2) C6H5CH2NHNH2 has molar mass 122; in (4) NaOH does not convert –CHO into –COOH, and EtOH does not convert –NH2 into –NHEt.
Answer: (3)