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Topic: Question on substitution mechanism  (Read 1952 times)

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Offline Firehchicken

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Question on substitution mechanism
« on: January 29, 2018, 08:00:34 AM »
So the question is : Which of the following mechanisms are acceptable for the reaction on the right to occur.

Answer to this question is choice C). I do not understand why.

I know that mechanism C is unacceptable cuz u cant have the electrons flowing to the nucleophile.

However, I cant see why mechanism A is incorrect. Likewise, I also cant see why Mechanisms B and D are correct.

What's the big deal with electrons moving around the oxygen??


Offline Babcock_Hall

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Re: Question on substitution mechanism
« Reply #1 on: January 29, 2018, 08:37:24 AM »
With respect to your last question, it may be that this motion is intended to portray an addition-elimination mechanism, meaning a mechanism in which the nucleophile adds in the first step and the leaving group departs in a subsequent step.  With respect to any of these mechanisms, I would give some thought to the question of whether or not a good leaving group is present.

Offline Firehchicken

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Re: Question on substitution mechanism
« Reply #2 on: January 29, 2018, 08:58:11 AM »
With respect to your last question, it may be that this motion is intended to portray an addition-elimination mechanism, meaning a mechanism in which the nucleophile adds in the first step and the leaving group departs in a subsequent step.  With respect to any of these mechanisms, I would give some thought to the question of whether or not a good leaving group is present.

I see. NH2 being a poor leaving group

Offline sjb

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Re: Question on substitution mechanism
« Reply #3 on: February 01, 2018, 06:56:31 AM »
Have you had any other thoughts why the others are incorrect? Hint - what does the arrow mean?

As to why the tetrahedral intermediate is implicated - I believe in some cases it has been isolated.

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