Which Nucleophile should I use?

[pharoh123]

Homework Statement

If I react butanol with toluenesulfonyl chloride (you can see that molcule here: http://sbillinghurst.files.wordpress.com/2010/03/440px-p-toluenesulfonyl_chloride_structure-svg.png) and Et3N and use H3C-CN as solvent what do I get?

The Attempt at a Solution

I know the first step is ejecting the Cl from the toluenesulfonyl chloride and then connecting the toluenesulfonyl group to the O from the butanol.
Then I deprotonoted the O with the toluenesulfonyl group with the Et3N using an acid/base reaction. I am then left with an excellent leaving group but I'm not sure what the nucleophile could be; the only good one I find is the Cl- I expulsed from the toluenesulfonyl chloride. Is that right?

 

[Mandeep Deka]

In Et3N there is a lone pair on N atom, which can behave as a nucleophile, but due to the three 'Et' groups, it becomes bulky and cannot act as a nucleophile. So, it acts as a base and an elimination reaction takes place, leading to the formation of but-1-ene!