The leaving group in an E2 reaction acts as a what?

[johnwandering]

A problem from BR Orgo:

In Hofmann Elimination, the amine acts as:
A.) both a nucleophile and a base
B.) a nucleophile only
C.) both an electrophile and a base
D.) an electrophile only

I am very very perplexed by this problem. I answered C in a heart beat because
1.) the amine picks off CH3 from I- in the beginning of the reaction ---> acting as a base
2.) the amine is released later via E2 reaction as a Leaving group ---> hence acting as an electrophile.


But BR decided to go with A, because of the identity of the free amine AFTER the reaction has ended.


Was this a misstep by BR? Why is their answer superior to my own?

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[SH3]

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[johnwandering]

A leaving group is an electrophile right?

 

[pm1]

A leaving group is an electrophile right?

No. Electrophile is what is being attacked by the nucleophile. While leaving groups are the substituents leaving the electrophile behind.

 

[SaintJude]

I think this is a weird question. In the hoffman elimination, the hydroxide group acts as a base.
And amine is usually a nucleophile b/c of the lone pairs, which confers electron density