[Carbo Mirakli]

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 + HC_nF_2n+1 <=> N(CH₃)₃H^{+ -}C_nF_2n+1

to get the products of [1] and [2] to yield,

[3]: R-C_nF_2n+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.

[Carbo Mirakli]

An example of reaction [2] using Fluoroform:

N(CH₃)₃ + HCF₃ <=> N(CH₃)₃H^{+ -}CF₃
[/b]
Can anyone corroborate that this example will occur to a sufficient extent that reaction [3] will proceed ? another take on it ?

reaction [3]:

R-N⁺(CH₃)₃Cl^- + N(CH₃)₃H^{+ -}CF₃ => R-CF₃ + HCl