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Question

Which of the following reaction is feasible for the preparation of 1-propoxy-2 methyl propane?

A
Williamson's synthesis of (Me2CHCH2ONa+MeCH2CH2Cl)
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B
Williamson's synthesis of (Me2CHCH2Cl+MeCH2CH2ONa)
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C
Alkoxymercuration-demercuration of (Me2C=CH2+MeCH2CH2OH)
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D
Alkoxy mercuration demercuration of propene with Me2CHCH2OH
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Solution

The correct options are
C Williamson's synthesis of (Me2CHCH2ONa+MeCH2CH2Cl)
D Williamson's synthesis of (Me2CHCH2Cl+MeCH2CH2ONa)


The reactions in options A and B are feasible for the preparation of 1-propoxy-2 methyl propane.

Alkoxy mercuration-demercuration of (Me2C=CH2+MeCH2CH2OH) or Alkoxy mercuration-demercuration of propene with Me2CHCH2OH will give the regioisomer of 1-propoxy-2 methyl propane as alkoxy group will be attached to more substituted C atom of C=C double bond.

Options A and B are correct.

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