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Topic: What are the products of these reactions?  (Read 3936 times)

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Offline IoanaD

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What are the products of these reactions?
« on: November 04, 2009, 03:23:07 AM »
Both of these reactions take place in the presence of an acid catalyst. For the second reaction I believe we get a cyclical compound like cyclic acetal (except instead of one of the oxygens there's a sulfur). Correct me if I'm wrong,
For the first reaction I'm kind of stuck... I'd really appreciate some enlightenment :S

Offline orgoclear

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Re: What are the products of these reactions?
« Reply #1 on: November 04, 2009, 03:25:27 AM »
for the first one, think about cleavage of the ester.

Offline azmanam

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Re: What are the products of these reactions?
« Reply #2 on: November 04, 2009, 06:06:30 AM »
the first one isn't an ester, it's a hemiacetal.  Think of what happens to hemiacetals under the reaction conditions
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Offline IoanaD

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Re: What are the products of these reactions?
« Reply #3 on: November 04, 2009, 09:51:14 AM »
AH! i don't know how i could miss that..hemiacetals react with an alcohol in the presence of an acid catalyst to produce an acetal! Ok, thanks for the eye-opener. I had the lecture on this today...
Is this correct for the second one?

Offline orgopete

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Re: What are the products of these reactions?
« Reply #4 on: November 04, 2009, 10:36:41 AM »
Yes, and if you apply the same mechanism to the first one, you should arrive at the correct answer for it as well. Hint, you are half-way there.
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Offline IoanaD

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Re: What are the products of these reactions?
« Reply #5 on: November 04, 2009, 08:50:15 PM »
So the first one would be something like this...i'm sorry, i've just begun working with these reactions.

Offline Scatter

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Re: What are the products of these reactions?
« Reply #6 on: November 04, 2009, 08:59:29 PM »
Don't apologize, you're doing great!  :)

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