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Topic: hydrolysis reaction  (Read 4215 times)

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Offline tcraw033

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hydrolysis reaction
« on: November 14, 2008, 01:20:34 PM »
I have this molecule and im supposed to show the hydrolysis of it there is two products and I have tried absolutley everything I think that the pentane ring on the right will have a double bond O coming off of it and the ring on the left will open up and have an OH group but nothing is working plese help.  The molecule is attached

Offline macman104

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Re: hydrolysis reaction
« Reply #1 on: November 14, 2008, 01:38:41 PM »
You should recognize the acetal functional group (1 carbon bonded to two "ethers").

http://bama.ua.edu/~kshaughn/chem232/resources/mechanisms/review/revacet/revacet1.htm

Offline tcraw033

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Re: hydrolysis reaction
« Reply #2 on: November 14, 2008, 01:44:36 PM »
Ok so which oxygen would be protonated?

Offline azmanam

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Re: hydrolysis reaction
« Reply #3 on: November 14, 2008, 01:56:46 PM »
Try them both.  See which one you like better.
Knowing why you got a question wrong is better than knowing that you got a question right.

Offline tcraw033

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Re: hydrolysis reaction
« Reply #4 on: November 14, 2008, 02:08:54 PM »
So I got most of the answer I have 0.9/1 and the hint says that: Normally, an acetal hydrolyzes to a carbonyl compound (ketone or aldehyde) and an alcohol under acidic conditions. In this particular case, though, entropy causes the hydroxy aldehyde to exist mostly in what form?   I have attached what i put as an answer im quite lost on where to go from here

Offline azmanam

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Re: hydrolysis reaction
« Reply #5 on: November 14, 2008, 02:15:50 PM »
All of organic chemistry works the same way: find a nucleophile, find an electrophile, nucleophiles attack electrophiles, repeat...

Take a look at your hydroxy aldehyde.  Is there a nucleophile?  Is there an electrophile?  Have the nucleophile attack the electrophile.
Knowing why you got a question wrong is better than knowing that you got a question right.

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