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Topic: ester nomenclature?  (Read 2799 times)

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Offline Adamk

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ester nomenclature?
« on: March 24, 2013, 02:21:06 PM »
Can anyone identify these ester nomenclatures please?

Offline Arkcon

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Re: ester nomenclature?
« Reply #1 on: March 24, 2013, 02:24:08 PM »
Per forum rules you should show your attempts at solving the problem before receiving help.

Can you begin to solve these on your own?  What are the names of at least one or two of the carbon chains on either side ot the oxygen in these two ethers?
Hey, I'm not judging.  I just like to shoot straight.  I'm a man of science.

Offline discodermolide

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Re: ester nomenclature?
« Reply #2 on: March 24, 2013, 02:24:45 PM »
The first is propyl benzoate, the second is methyl 4-methylpentanoate.
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Offline Adamk

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Re: ester nomenclature?
« Reply #3 on: March 24, 2013, 02:30:41 PM »
I am pretty sure that the first two are correct. I'm having trouble figuring out how to put the 2 together to form the product.

Offline discodermolide

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Re: ester nomenclature?
« Reply #4 on: March 24, 2013, 02:48:51 PM »
So your reaction is acetyl chloride + dimethylamine to give a product?
How do amines react with acid chlorides?
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Offline Adamk

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Re: ester nomenclature?
« Reply #5 on: March 24, 2013, 02:58:44 PM »
Yes, the question asks for the 3 products that are left after those 2 react together. Acid chlorides react with amines to form amides, I think? I'm having trouble on how to draw the molecule that has the 2 put together. I know that the protonated amine will be left, along with a molecule of the original acid chloride. I know that the nucleophile adds to the carbonyl carbon which forms a tetrahedral intermediate and that the tetrahedral intermediate loses a proton. I also know that the chlorine is eliminated because the chloride ion is a weaker base.

Offline discodermolide

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Re: ester nomenclature?
« Reply #6 on: March 24, 2013, 03:06:36 PM »
Yes acid chlorides react with amines to give amides, in this case this one.
CC(N(C)C)=O
If you have an excess of dimethylamine, you will get dimethylamine hydrochloride, C[NH2+]C.[Cl-].
In the case of equivalent amounts you will end up with a mixture of all three compounds.
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