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Author Topic: how to prepare these products  (Read 1648 times)

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whyohme

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how to prepare these products
« on: August 24, 2012, 02:06:17 PM »



how to get butanoic acid and hexanoic acid at the same time from 1-bromopentane?

Thanks!
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discodermolide

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Re: how to prepare these products
« Reply #1 on: August 24, 2012, 02:16:55 PM »



how to get butanoic acid and hexanoic acid at the same time from 1-bromopentane?

Thanks!

Hexanoic acid is easy, butanoic acid need a bit more thought.
Have you any ideas?
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whyohme

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Re: how to prepare these products
« Reply #2 on: August 24, 2012, 04:25:49 PM »



how to get butanoic acid and hexanoic acid at the same time from 1-bromopentane?

Thanks!

Hexanoic acid is easy, butanoic acid need a bit more thought.
Have you any ideas?



I came up with this. I have no idea how to obtain hexanoic acid. I dont find any example shows "more-carboned product" example. please help. thanks
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discodermolide

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Re: how to prepare these products
« Reply #3 on: August 24, 2012, 06:08:46 PM »

That's OK for the first one.
The second one is you make a Grignard reagent with magnesium then treat it with CO2. There the chain goes from 5 carbons to 6!
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orgopete

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Re: how to prepare these products
« Reply #4 on: August 24, 2012, 06:08:51 PM »

You might want to check the reagents for the elimination so you don't get substitution, but otherwise fine.

Hexanoic acid hint, if bromopentane is made into a nucleophile, then what electrophile will give the acid upon workup?
A second option is if bromopentane is the electrophile, what one carbon nucleophile will give the same oxidation state as a carboxylic acid (it will give a carboxylic acid after hydrolysis)?
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whyohme

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Re: how to prepare these products
« Reply #5 on: August 24, 2012, 06:57:28 PM »

That's OK for the first one.
The second one is you make a Grignard reagent with magnesium then treat it with CO2. There the chain goes from 5 carbons to 6!


thank you
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whyohme

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Re: how to prepare these products
« Reply #6 on: August 24, 2012, 07:09:49 PM »

You might want to check the reagents for the elimination so you don't get substitution, but otherwise fine.

Hexanoic acid hint, if bromopentane is made into a nucleophile, then what electrophile will give the acid upon workup?
A second option is if bromopentane is the electrophile, what one carbon nucleophile will give the same oxidation state as a carboxylic acid (it will give a carboxylic acid after hydrolysis)?

if bromopentane is electrophile, CO2 will be the nucleophile ?   
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orgopete

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Re: how to prepare these products
« Reply #7 on: August 25, 2012, 05:29:47 AM »

No CO2 is an electrophile. The carbon will accept electrons, for example from a Grignard reagent. You need the carbon to possess electrons than can be donated. Hint, it is a one carbon nucleophile with a nitrogen attached.
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