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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.