[figure] Identify (P)
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Answer
(4) [figure]
Solution
Step 1: Zn, removes the two vicinal Br atoms (dehalogenation) a C=C bond is formed between the two carbons that carried Br.
Step 2: H+ of HBr adds to the double bond a 2° carbocation is formed next to either the ethyl-bearing or the methyl-bearing ring carbon.
A 1,2-hydride shift converts this 2° carbocation into a more stable 3° carbocation.
The 3° carbocation on the methyl-bearing carbon has 7 α-H atoms (3 of CH3 + 2 + 2 of the ring CH2 groups), while the one on the ethyl-bearing carbon has only 6 α-H atoms (2 of CH2CH3 + 2 + 2),
the carbocation on the carbon carrying CH3 is more stabilised by hyperconjugation.
Br- attacks this carbocation:
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(P) is 1-bromo-3-ethyl-1-methylcyclopentane, i.e. option (4).
Answer: (4)