Well
This is a protonated solution which presupposes the SN1
ROH -> attacks HCl to make ROH2+ and Cl-
the H2O leaves, R+ is left behind. Now for R+ to be most stable you should have a tert alkyl to stabilize the positive charge
This allows Cl- to now act as a nucleophile to attack. giving you RCl
Wow, I've probably done at least a hundred orgo problems about SN1/SN2 and never knew this before. I just figured since Cl- is strong, the alcohol would become ROH2, and the Cl- would attack this for SN2. I had no idea the H20 group left first.
yeah, whenever you see an alcohol or ketone oxygen in an acidic solution , just assume that the oxygen gets a hydrogen first.
If the oxygen has 2 hydrogens, it is a good leaving group and usually leaves of it's own accord due to it being water. So you'd assume that would be the next step. would leave a carbocation which you'd need electron cloud stabilization for like a tertiary substituted carbon.
I just barely remembered that tidbit from orgo (2005-2006)... oh and maybe some studying from 2009 when I took mcat then.
Yeah ROH2+ the H2O is an awesome leaving group because when it leaves it's neutral, as opposed to ROH --> OH- leaving = poor LG
Yes, polar protic favors SN1 because it reduces nucleophile/base strength, thereby hindering SN2/E2. And yes, SN1 are faster with tertiary and secondary substrate.
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