[Q]Destroyer orgo #65

[hunterpostbacst]

The question is which one reacts fastest in an SN1 type between t-butylbromide and t-butyliodide.

My understanding is that both are 3rd degrees and I would see which one has a better leaving group.
Absolutely, compared to Br, I is a better leaving group in general.

However, in protic solvent, isn't Br is a better leaving group?

In kaplan blue book, the bigger size it is, the more nucleophile it is only in protic.

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[lonhosilver]

the one with the iodine because it is a better leaving group... if everything is equal in terms of carbocation and solvent(and it looks like it is from what u wrote) then you look at the hailde/leaving group and the the stregth of the leaving groups is(in terms of halides):

I>Br>Cl>F