# Problem: Which sequence of reactions below gives the highest yield of ethyl isopropyl ether? CH3CH2OCH(CH3)2    ethyl isopropyl ether A) (1) CH3CH2OH + Na     (2) (CH 3)2CHBr B) (1) (CH3)2CHOH + Na   (2) CH 3CH2Br C) (1) (CH3)2CHOH + Na   (2) CH 3CH2OH D) (1) CH3CH2OH  + Na    (2) (CH 3)2CHOH

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###### Problem Details

Which sequence of reactions below gives the highest yield of ethyl isopropyl ether?

CH3CH2OCH(CH3)2    ethyl isopropyl ether

A) (1) CH3CH2OH + Na     (2) (CH 3)2CHBr

B) (1) (CH3)2CHOH + Na   (2) CH 3CH2Br

C) (1) (CH3)2CHOH + Na   (2) CH 3CH2OH

D) (1) CH3CH2OH  + Na    (2) (CH 3)2CHOH

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Our tutors have indicated that to solve this problem you will need to apply the Williamson Ether Retrosynthesis concept. If you need more Williamson Ether Retrosynthesis practice, you can also practice Williamson Ether Retrosynthesis practice problems.

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Based on our data, we think this problem is relevant for Professor Thimmaiah's class at University of Washington Bothell.