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Topic: Racemic mixture of mandelic acid and aminobutane.  (Read 3617 times)

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Offline actionbasterd

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Racemic mixture of mandelic acid and aminobutane.
« on: October 19, 2011, 10:58:29 PM »
Racemic mixture of mandelic acid + aminobutane = 2 products.

I have no idea how to begin here. I do have a reference to look at for the racemic mix of AMINOBUTANE and pure mandelic acid, but not the other way around, and I am lost.
Thanks so much.

A guess would be that the OH that is near the doulbe bond O would be replaced with the whole structure of aminobutane EXCEPT for the fact that the H2N would be an HN. Then, the diastereomer of this is the other product. This is just a guess.

Offline discodermolide

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Re: Racemic mixture of mandelic acid and aminobutane.
« Reply #1 on: October 20, 2011, 01:14:25 AM »
Racemic mixture of mandelic acid + aminobutane = 2 products.

I have no idea how to begin here. I do have a reference to look at for the racemic mix of AMINOBUTANE and pure mandelic acid, but not the other way around, and I am lost.
Thanks so much.

A guess would be that the OH that is near the doulbe bond O would be replaced with the whole structure of aminobutane EXCEPT for the fact that the H2N would be an HN. Then, the diastereomer of this is the other product. This is just a guess.

I assume you are using one of the chiral mandelic acids? If that is the case you have here an acid/base reaction producing a salt.
One of the components is chiral so you have two compounds (salts) a diastereoisomeric mixture.
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Offline fledarmus

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Re: Racemic mixture of mandelic acid and aminobutane.
« Reply #2 on: October 20, 2011, 08:24:34 AM »
Just aminobutane? Not 1-aminobutane or 2-aminobutane?

This is an acid/base reaction as discodermolide said - the mandelic acid is deprotonated and the aminobutane is protonated, and you get a salt formed from the deprotonated acid and the protonated amine. Each salt is a different product with different properties - how many salts will you get? In your racemic mixture, you have both (R)-mandelic acid and (S)-mandelic acid. You have a reference that tells you how many compounds you get when you react a single enantiomer of mandelic acid with a racemic mixture of (I'm guessing) (R) and (S) 2-aminobutane - does the number of compounds you actualy see tell you anything about the mixture you went in with?

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