A research paper in the Journal of the American Chemical Society describes the p
ID: 890318 • Letter: A
Question
A research paper in the Journal of the American Chemical Society describes the preparation of trifluoromethanol, CF3OH, and trifluoromethylamine, CF3NH2, two compounds that had not been prepared until recently because of their tendency to lose HF to form multiple bonds. The compounds were found to be reasonably stable at temperatures around 0 degree C. The authors of the paper report that "CF3OH is certainly not a typical alcohol but rather an acid." They also say that "CF3OH is of surprisingly high volatility" (meaning that it has a much lower boiling point than expected). For CF3NH2, they report that "the basic character of CF3NH2 is lower than the basicity of normal organic bases like (CH3)3N." How would you rationalize each of the three observations quoted? On the basis of the information given above, complete the following equation and show which way equilibrium will lie. CF3NH3+ Cl- + (CH3)3 N rightarrowExplanation / Answer
first statement
CF3OH -----> CF3O- + H+
generally alcohols are week acids but CF3OH is more acidic almost like acid this is because the conjugate base generated from CF3OH is stabilised by CF3 group through inductive effect because F will exhibit strong -I effect
statement-2
this is because the hydrogen bonding between the molecules will decrease because of fluorine atoms thats why boiling point will decrease.
statement -3
here basicity means electron donating capacity CH3 groups are electron donating groups so all three alkyl groups will donate electrons to the nitrogen so nitrogen will become more basicity
where as CF3 group is electron with drawing group that will decrease the electron density at the nitrogen so basicity will decrease.
b)
CF3N+H3Cl- + (CH3)3N -----------> CF3NH2 + (CH3)3N+HCl-
equlibrium is shift towards right
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