Problem: Starting with optically pure (R) or (S)-2-butanol which method below would give the best yield of the following ether? a) (1) (R)-2-butanol + TsCl    (2) CH 3ONa b) (1) (S)-2-butanol + TsCl     (2) CH 3ONa c) (1) (R)-2-butanol + Na       (2) CH 3I d) (1) (S)-2-butanol + Na       (2) CH 3I

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Problem Details

Starting with optically pure (R) or (S)-2-butanol which method below would give the best yield of the following ether?

a) (1) (R)-2-butanol + TsCl    (2) CH 3ONa

b) (1) (S)-2-butanol + TsCl     (2) CH 3ONa

c) (1) (R)-2-butanol + Na       (2) CH 3I

d) (1) (S)-2-butanol + Na       (2) CH 3I

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Based on our data, we think this problem is relevant for Professor Song's class at University of the District of Columbia.