Why is the rate of quaternization of #"triethylamine"# FASTER than that of #HC{CH_2CH_2}_3N#, #"quinuclidine"#?

1 Answer
Feb 17, 2018

Are you sure this is the case?

Explanation:

You have got TWO tertiary amines....#Et_3N# versus #HC{CH_2CH_2}_3N#..for the bicyclo-amine, the hot end, the nitrogen lone-pair is arguably more exposed, and LESS sterically encumbered than the lone pair on triethylamine. In any case, I would like to see some data that establish the faster reaction rate of quinuclidine under bond-making conditions, with respect to the two amines....

In both instances, the product will be a quaternary ammonium salt...