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Choose the Best Answer · Q16

Q.Identify the compound (A) in the following reaction
(a cyclohexane ring carrying an exocyclic =CH-C6H5 double bond) →ii) Zn/H2Oi) O3\xrightarrow[\text{ii) Zn/H}_2\text{O}]{\text{i) O}_3} cyclohexanone + (A)

(a) an aromatic ring with -CHO (benzaldehyde)
(b) a saturated cyclohexane ring with -CHO (cyclohexanecarbaldehyde)
(c) an aromatic ring with -OH (phenol)
(d) an aromatic ring with -COOH (benzoic acid)
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Step 1. The starting material is a cyclohexane ring with an EXOCYCLIC double bond, ring-C=CH-C6H5 (a benzylidenecyclohexane), reacted with O3 then Zn/H2O -- a standard reductive ozonolysis, cleaving that one C=C bond into two separate carbonyl fragments.

Step 2. The RING carbon of the double bond becomes a ring C=O -- since it is flanked by two ring CH2 groups (no H on that alkene carbon itself, both substituents being ring carbons), this fragment is a ketone: cyclohexanone (already given as the other, main product in the question).

Step 3. The EXOCYCLIC carbon of the double bond, =CH-C6H5, carries one phenyl group and one H, so on cleavage it becomes an aldehyde: C6H5-CHO, benzaldehyde -- this is compound (A). …

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