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Question

Suppose the double bonded methylene group of 1-bromo-2-propene is labelled with 13C,H213C=CH−CH2Br. What product will be formed by methanolysis of this substrate?

A
H213C=CHCH2OCH3 and H2C=CH13CHOCH3
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B
H2C=13CHCH2OCH3
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C
H213C=CHCH2OCH3
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D
H2C=CH13CH2OCH3
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Solution

The correct option is A H213C=CHCH2OCH3 and H2C=CH13CHOCH3
Two products are obtained. In the first product, the bromine atom is replaced by the methoxy group. In the second product, the Br atom is replaced by the methoxy group and the double bond is also rearranged.
13CH2=CHCH2BrCH2OH−−−−HBr13CH2=CHCH2OCH3+CH2=CH13CH2OCH3

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