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In the following reaction sequence starting from cyclohexane carboxamide, find x = the number of oxygen atoms in compound D: cyclohexane carboxamide --Br2/KOH--> A --HNO2/H2O--> B --conc. H2SO4, heat--> C --KMnO4/H+, heat--> D --LiAlH4--> E --SOCl2 (1 eq.)--> F --NaH--> G --cyclisation--> H

1. 1
2. 2
3. 3
4. 4

Correct answer: 4

Solution

Step-by-step: A: Cyclohexane carboxamide + Br2/KOH (Hofmann degradation) -> cyclohexylamine (A). B: Cyclohexylamine + HNO2 (NaNO2/HCl or HNO2) -> diazonium salt -> cyclohexanol (B) (in H2O, diazonium decomposes to give alcohol). C: Cyclohexanol + conc. H2SO4/heat -> cyclohexene (C) (dehydration/elimination). D: Cyclohexene + KMnO4/H+/heat (hot acidic) -> oxidative cleavage of the C=C in the ring -> ring opens -> hexanedioic acid (adipic acid: HOOC-(CH2)4-COOH) (D). Number of O atoms in adipic acid = 4 (two COOH groups, each with 2 O). So x = 4.

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