Problem: Which is the best way to prepare 3-methoxypentane via the Williamson method? A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140'CB). CH3OH + (CH3)2CHCH2CH2OH+ H2SO4, 140' CC). CH3ONa + (CH3CH2)2CHBrD). CH3I + (CH3CH2)2CHONa

FREE Expert Solution

Williamson ether synthesis → Follows SN2 mechanism → prefers least substituted LG and alkoxide as nucleophile

Analyzing each reaction:

A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140°C → alcohol + H2SO → acid-catalyzed hydration

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Problem Details

Which is the best way to prepare 3-methoxypentane via the Williamson method? 

A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140'C

B). CH3OH + (CH3)2CHCH2CH2OH+ H2SO4, 140' C

C). CH3ONa + (CH3CH2)2CHBr

D). CH3I + (CH3CH2)2CHONa

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