[figure] 'P' is
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Answer
(3) [figure]
Solution
(i) KOH (alc.): dehydrobromination of the vicinal dibromide gives 1-bromocyclooctene.
(ii) NaNH2: a second dehydrobromination gives cyclooctyne (the smallest isolable cycloalkyne).
(iii) Hg2+/H+: hydration of the C≡C gives an enol, which tautomerises to cyclooctanone.
(iv) Zn-Hg/H+ (Clemmensen reduction): >C=O >CH2, giving cyclooctane.
C8H14Br2 alc. KOH C8H13Br NaNH2 C8H12 Hg2+/H+ C8H14O Zn-Hg/H+ C8H16
P = cyclooctane.
Answer: (3)