I have been considering the following reactions (text book problem):
[1]: R-CL + N(CH3)3 => R-N+(CH3)3Cl-
and
[2]: N(CH3)3 + HCnF2n+1 <=> N(CH3)3H+ -CnF2n+1
to get the products of [1] and [2] to yield,
[3]: R-CnF2n+1 + HCl
My problem is that I am not sure if reaction [2] will form the equilibrium shown. Can the tert amine increase the polarity of the hydrogen-carbon of the n-HydroFluoroCarbon sufficiently to yield [3] ?
I believe so but am not certain. The H-C bond should have a small polarity due to the e-withdrawing nature of the fluorines of the HFC and I feel that the tert-amine will partially donate its e-pair to the partially positive H thus augmenting the polarity of the H-C bond.