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Topic: Carbonyl Substitution Reaction  (Read 2250 times)

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Offline Mushrooomboy

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Carbonyl Substitution Reaction
« on: November 11, 2012, 12:16:17 PM »
Hi, so I'm wondering if I did this substitution reaction right. The only thing that the book did differently is that, it didn't transfer the proton to the other oxygen. I'm wondering is the mechanism that I wrote is still valid or not? It's question 7a by the way, I've attached the question and my answer. Any input would be greatly appreciated  ;D

Offline discodermolide

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Re: Carbonyl Substitution Reaction
« Reply #1 on: November 11, 2012, 02:01:25 PM »
You are making an acid anhydride. After you hydrolysed the acid chloride to the acid what do you think happens then?
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Offline Mushrooomboy

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Re: Carbonyl Substitution Reaction
« Reply #2 on: November 11, 2012, 06:21:06 PM »
2 of the intermediates will come together, the C=O from 1 will attack the ketone on the other to form the product, right?

Offline Mushrooomboy

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Re: Carbonyl Substitution Reaction
« Reply #3 on: November 11, 2012, 06:21:29 PM »
the 2 electrons from the C=O pi bond I mean

Offline discodermolide

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Re: Carbonyl Substitution Reaction
« Reply #4 on: November 11, 2012, 10:06:38 PM »
2 of the intermediates will come together, the C=O from 1 will attack the ketone on the other to form the product, right?

They sound like long lost lovers :P
The compounds are not ketones, one is an carboxylic acid chloride, the other is a carboxylic acid. If water can attack (hydrolyse) the acid chloride what do you think the carboxylic acid can do?
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