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Topic: Esters & Epoxides - What to look for in solving?  (Read 3105 times)

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Offline disneygurl2010

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Esters & Epoxides - What to look for in solving?
« on: February 05, 2012, 03:51:17 PM »
Esters & Epoxides - What to look for in solving these different problems?

Offline discodermolide

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Re: Esters & Epoxides - What to look for in solving?
« Reply #1 on: February 05, 2012, 04:32:54 PM »
Esters & Epoxides - What to look for in solving these different problems?

What are your ideas here?
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Offline disneygurl2010

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Re: Esters & Epoxides - What to look for in solving?
« Reply #2 on: February 05, 2012, 05:08:14 PM »
I'm thinking for the first one, since there is a strong based present, the epoxide will break up.  The one with R,R-(+)-diethyltartrate will form an epoxide pointing down in space.  The 3rd, I am not quite sure where to start =/

Offline discodermolide

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Re: Esters & Epoxides - What to look for in solving?
« Reply #3 on: February 05, 2012, 05:11:53 PM »
I'm thinking for the first one, since there is a strong based present, the epoxide will break up.  The one with R,R-(+)-diethyltartrate will form an epoxide pointing down in space.  The 3rd, I am not quite sure where to start =/

I think you got them mixed up. Please start again from the top going sequentially down the list. Then I might understand what you are saying.
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Offline disneygurl2010

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Re: Esters & Epoxides - What to look for in solving?
« Reply #4 on: February 05, 2012, 05:24:27 PM »
For the first one, I think that TsOH is a strong acid but MeOH is a strong base..?  so it would perhaps break the epoxide into an alkane in the final product?

For the second, EtN I know is a good amine base but I am not sure where to go from here.

For the last, the solvent at the bottom makes a product that has an epoxide with the ring but perhaps it has chirality and points up?

Offline discodermolide

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Re: Esters & Epoxides - What to look for in solving?
« Reply #5 on: February 05, 2012, 05:30:50 PM »
For the first one, I think that TsOH is a strong acid but MeOH is a strong base..?  so it would perhaps break the epoxide into an alkane in the final product?

For the second, EtN I know is a good amine base but I am not sure where to go from here.

For the last, the solvent at the bottom makes a product that has an epoxide with the ring but perhaps it has chirality and points up?

The first one is a simple acid catalyzed epoxied opening to give an alcohol.
The second is a protection of the primary alcohol.
The third is a Sharpless epoxidation.
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