Comments on: The Most Annoying Exceptions in Org 1 (Part 2)

By: DM

DM — Sun, 27 Sep 2020 07:04:14 +0000

Another on: very poor leaving groups (as F-) lead to Hofmann products. The reason is due to electronic reasons (similar to what is happening electronically with quaternary ammonium leading to amine leaving group).

By: James Ashenhurst

James Ashenhurst — Thu, 05 Sep 2019 18:33:37 +0000

In reply to karishma. Would just be neopentyl alcohol. SN2. Although the reaction would be pretty slow.

By: mks

mks — Sat, 22 Sep 2018 07:55:46 +0000

Excellent!. I agree with you: I wish such sites were present when i was beginning to learn chemistry way back when

By: karishma

karishma — Sat, 03 Dec 2016 17:07:02 +0000

Then what is the product formed when neopentyl bromide reacts with NaOH?? N whats the mechanism behind it?

By: Edison

Edison — Fri, 11 Mar 2016 07:52:32 +0000

It seems the attempt to clear common Misconceptions is the main focus here.

By: Shruti

Shruti — Wed, 02 Mar 2016 05:39:21 +0000

Hi James!
I am an Indian student, preparing for my medical entrances. I have loved organic from the very beginning but somehow there were always some uncertanities in my mind while solving questions. You have cleared many of my concepts with your easy explanation which our professors fail to do. Thank you! God bless you.

By: James

James — Tue, 16 Jun 2015 02:21:50 +0000

In reply to Nathalie. Well, there's "racemization". So both (R) and (S) will form. One of those stereocenters will represent retention of configuration, the other will represent inversion.

By: Nathalie

Nathalie — Fri, 12 Jun 2015 11:24:57 +0000

In reply to James. Hi James, that comment confused me a bit. How is there inversion in a Sn1 reaction? I thought inversion was specifically in Sn2 reactions. On another note, really appreciate your awesome "breakdowns" of complicated mechanisms. Thank you for all your work!

By: D. Blanco

D. Blanco — Sun, 29 Mar 2015 10:30:17 +0000

These are not “exceptions” (parts 1 and 2). You create them by starting from wrong (or half-true) statements. It’s not didactic to explain things wrong and later complete the explanations calling them “exceptions”. Explain everything from the beginning, it’s less sensationalist, but people will understand it better. This is just a humble advice after having taught Organic Chemistry for 25 years.

By: James

James — Mon, 09 Mar 2015 03:19:35 +0000

In reply to Linsu.

Thanks for commenting!
It’s similar, but not quite the same, as an SN1, because it does not go through a free carbocation. The difference is stereochemistry. In an SN1, there is both retention and inversion of stereochem. In the opening of epoxides under acidic conditions, there is only inversion. So it is ‘SN1-like’.