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

Question

Which is the best way to prepare 3-methoxypentane via the Williamson method? ( please explain why) A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140'C B). CH3OH + (CH3)2 CHCH2CH2OH+ H2SO4, 140' C C). CH3ONa + (CH3CH2)2CHBr D). CH3 I + (CH3CH2)2CHONa Which is the best way to prepare 3-methoxypentane via the Williamson method? ( please explain why) A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140'C B). CH3OH + (CH3)2 CHCH2CH2OH+ H2SO4, 140' C C). CH3ONa + (CH3CH2)2CHBr D). CH3 I + (CH3CH2)2CHONa Which is the best way to prepare 3-methoxypentane via the Williamson method? ( please explain why) A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140'C B). CH3OH + (CH3)2 CHCH2CH2OH+ H2SO4, 140' C C). CH3ONa + (CH3CH2)2CHBr D). CH3 I + (CH3CH2)2CHONa A). CH3OH + CH3CH2CHOHCH2CH3 + H2SO4, 140'C B). CH3OH + (CH3)2 CHCH2CH2OH+ H2SO4, 140' C C). CH3ONa + (CH3CH2)2CHBr D). CH3 I + (CH3CH2)2CHONa

Explanation / Answer

This method is suitable for the preparation of a wide variety of unsymmetric ethers. The nucleophilic substitution of halides with alkoxides leads to the desired products.

If the halides are sterically demanding and there are accessible protons in the ?-position, the alkoxide will act as a base, and side products derived from elimination are isolated instead.

Option D

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