November 30, 2022, 06:45:05 AM
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Topic: Organic Chemistry Problem  (Read 852 times)

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Offline JoeyBob

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Organic Chemistry Problem
« on: January 31, 2020, 09:00:20 PM »
Can someone explain WHY my mechanism doesn't work and SHOW me the proper mechanism for the answer. I asked this quest. before but the answers weren't very good.

Yes, I know it's an elimination. I want to know WHY it's an elimination and not my way and HOW the elimination occurs. Because I don't understand it and i'll actually need an explanation to gain an understanding.

Offline JoeyBob

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Re: Organic Chemistry Problem
« Reply #1 on: January 31, 2020, 09:20:17 PM »
Is it because it's not diluted acid and the acid protonates the oxygen twice, forming a water leaving group?


Offline JoeyBob

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Re: Organic Chemistry Problem
« Reply #2 on: January 31, 2020, 09:23:13 PM »
Is it because it's not diluted acid and the acid protonates the oxygen twice, forming a water leaving group?

But then where do the electrons for the elimination come from if the water takes two when leaving, leaving behind a cation?

Offline hollytara

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Re: Organic Chemistry Problem
« Reply #3 on: January 31, 2020, 10:27:26 PM »
From the H+ that is also lost, leaving behind the electron pair.

Check out the book by Jakob Fredlos - has just enough details!

Offline JoeyBob

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Re: Organic Chemistry Problem
« Reply #4 on: January 31, 2020, 11:57:47 PM »
From the H+ that is also lost, leaving behind the electron pair.

Check out the book by Jakob Fredlos - has just enough details!

So like this?

Offline kriggy

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Re: Organic Chemistry Problem
« Reply #5 on: February 01, 2020, 07:29:15 AM »
Not quite but almost. Since its tertiary alcohol it will likely go  through carbocation rather than single step

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