[orbital_90]

Hello,
I just have a question about making ethers. (This is from our study session for Org. Chem 2)
The question is:

Which pair of reagents would produce the highest yield of (R)-2-ethoxybutane?

a) sodium (S)-2-butoxide + iodoethane
b) sodium (R)-2-butoxide + iodoethane
c) sodium ethoxide + (S)-2-iodobutane
d) sodium ethoxide + (R)-2-iodobutane
e) both B and C

[discodermolide]

What do you think the answer to this is?

[orgopete]

Hint, if elimination were the competing reaction, which reactions would be most likely to undergo elimination?