[burntbread07]

How can you show how you would convert (R)-2-heptanol into (R)-2-heptanethiol?

At first I thought adding NaSH would be fine until I came across this website:
http://pubs.acs.org/cgi-bin/abstract.cgi/jafcau/2004/52/i02/abs/jf035008h.html
http://pubs.acs.org/isubscribe/journals/jafcau/52/i02/figures/jf035008hh00001.html

I don't see how this can be expected from an undergrad orgo student, only 5 weeks in.  Would an SN2 reaction involving 2-heptanol and NaSH be sufficient?  Or does that not readily occur, meaning another step has to be included in the process?

[Yggdrasil]

I don't think that your prof would necessarily expect you to include tosylation or thioacetylation steps in your answer. 

However, as written, your answer is incorrect.  What product would you expect in an SN2 reaction between (R)-2-heptanol and NaSH?

[burntbread07]

(R)-2-heptanol + NaSH ---> (?)-2-heptanethiol + NaOH

Does the reaction with NaSH invert the configuration, resulting in (S)-2-heptanethiol?

[Yggdrasil]

Yes, SN2 reactions result in inversion.

[adam]

One way:
First running a mitsunobu reaction, to invert the configuration of the alcohol, and then once you have the S-heptanol, convert the alcohol in a good leaving group and run a Sn2 reaction.

Maybe is possible to do the direct mitsunobu reaction using as a Nucleophile HS-R (is more acidic than the alcohol and shoulb be work...) but I'm not sure.