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Question

Give steps involved in the conversion of 1-iodo-2-methylcylopentane to 1-methylcyclopentanol.


A

KOH; Hg(OAc)2 and H2O; NaBH4

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B

KOH; NaOH+CaO; Zn

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C

KOH; LiAlH4; Na

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D

KOH; NaBH4; Zn

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Solution

The correct option is A

KOH; Hg(OAc)2 and H2O; NaBH4


The first is the E2 elimination that gives the trisubstituted alkene as the major product. The resulting alkene (major product) is subjected to oxymercuration-demercuration to get the required product: 1-methylcyclopentanol.


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