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Topic: Hydrate of an Aldehyde  (Read 4012 times)

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Offline AlphaScent

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Hydrate of an Aldehyde
« on: September 10, 2014, 01:18:13 PM »
I was reading on organic-chemistry.org about Jones reagent and it says if an aldehyde is able to form the hydrate it will be further oxidized to the carboxylic acid.

Why would an aldehyde not form a hydrate?  What would hinder it?

If I have a aldehyde alpha branched from a longer chain wouldnt it oxidize to the acid??

I am wondering what would hinder the oxidation??

Vinyl, allylic??
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Offline phth

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Re: Hydrate of an Aldehyde
« Reply #1 on: September 10, 2014, 04:40:11 PM »
Im guessing sterics, next to EDG, solvent.  Jones will form epoxides on double bonds (allylic) as a side reaction and carbocation shift (allylic). Take away acetal by distilling.  Jones reagent can cause explosions.
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Offline AlphaScent

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Re: Hydrate of an Aldehyde
« Reply #2 on: September 11, 2014, 09:28:21 AM »
This is what I am trying to do.  I do no think I should have a probelm.
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Offline discodermolide

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Re: Hydrate of an Aldehyde
« Reply #3 on: September 11, 2014, 10:42:37 AM »
You would be better with a Pinnick oxidation.
http://en.wikipedia.org/wiki/Pinnick_oxidation

The Jones reagent, Cr is, well I don't like it :o
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Offline AlphaScent

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Re: Hydrate of an Aldehyde
« Reply #4 on: September 11, 2014, 10:56:20 AM »
That seems more than a feasible way to go.

Do you just have a grudge against Chromium??? 

Nasty work up I assume?!?!
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Offline discodermolide

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Re: Hydrate of an Aldehyde
« Reply #5 on: September 11, 2014, 11:01:21 AM »
Work-up is s#*$. Hate Cr oxidants.
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Offline AlphaScent

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Re: Hydrate of an Aldehyde
« Reply #6 on: September 11, 2014, 11:03:08 AM »
I concur.  Dread them.
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Offline discodermolide

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Re: Hydrate of an Aldehyde
« Reply #7 on: September 11, 2014, 11:06:14 AM »
Very clever this forum it changed my s#*$ to s#*$ :o
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Offline AlphaScent

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Re: Hydrate of an Aldehyde
« Reply #8 on: September 11, 2014, 02:56:17 PM »
Yes.  I have tried to cuss on here before and it changes what you write.  f&#$.
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Offline discodermolide

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Re: Hydrate of an Aldehyde
« Reply #9 on: September 11, 2014, 03:14:14 PM »
I was not cussing, it was valid chemical terminology!
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Offline AlphaScent

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Re: Hydrate of an Aldehyde
« Reply #10 on: September 11, 2014, 03:20:07 PM »
hahaha  ;D
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Offline AWK

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Re: Hydrate of an Aldehyde
« Reply #11 on: September 12, 2014, 05:58:13 AM »
Quote
Why would an aldehyde not form a hydrate?  What would hinder it?

Some aldehydes form quite stable hydrates, eg CCl3CHO. The majority of aldehydes exist as partial
hydrates in aqueous solution.
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