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Topic: Draw the major organic product of the following?  (Read 18425 times)

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Offline theanonymous

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Draw the major organic product of the following?
« on: March 25, 2013, 06:10:54 PM »
Question 5)


From my notes in class, this is what I have:

On the first ester equivalent, the alpha proton is removed creating a nucleophilic carbon of the enolate ion. This nucleophilic alpha-carbon attacks the electrophilic carbonyl carbon of the second ester equivalent which throws up the pi bond into a lone pair on the oxide oxygen to form the tetrahedral which intermediate, then comes back down to "spit out" the alkoxide ion which quickly deprotonates the "carbonyl sandwiched" alpha proton. This leaves behind an enolate ion and the alcohol. The acid workup protons the enolate ion at carbon eventually. (May go through tautomerization.)

Species A:

CC[CH-]C(=O)OCC

This is wrong :(

I have one more submission left for species A.

Species B:

CCCC(O)OCC

This is wrong too :(
« Last Edit: March 25, 2013, 06:58:10 PM by theanonymous »
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Offline theanonymous

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Re: Urgent help needed with Saponification and other mechanisms!
« Reply #1 on: March 25, 2013, 06:19:19 PM »
Question 6)



This is a similar problem

Question 9)



I completely messed up on this one


Question 11)




This one looked similar to 6 and 5 but I STILL got it wrong :'(
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #2 on: March 25, 2013, 07:50:30 PM »
 ??? ???
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Offline discodermolide

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Re: Draw the major organic product of the following?
« Reply #3 on: March 25, 2013, 08:14:34 PM »
questions 5, and 9 are Claisen condensations http://en.wikipedia.org/wiki/Claisen_condensation
question 11 is an aldol condensation.
question 6 we have done already and has nothing to do with the other reactions.
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #4 on: March 25, 2013, 08:29:13 PM »
Quote from: discodermolide on March 25, 2013, 08:14:34 PM
questions 5, and 9 are Claisen condensations http://en.wikipedia.org/wiki/Claisen_condensation
question 11 is an aldol condensation.
question 6 we have done already and has nothing to do with the other reactions.

For 5, is species A this then?

CCOC(=O)CCCC(C)=O
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Offline discodermolide

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Re: Draw the major organic product of the following?
« Reply #5 on: March 25, 2013, 08:40:07 PM »
No that is not species A. The proton alpha to the carbonyl of one ester attacks the carbonyl of the other ester.
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #6 on: March 25, 2013, 09:05:06 PM »
Quote from: discodermolide on March 25, 2013, 08:40:07 PM
No that is not species A. The proton alpha to the carbonyl of one ester attacks the carbonyl of the other ester.

Is the answer CCCC(=O)C(CC)C(=O)OCC?
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Offline discodermolide

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Re: Draw the major organic product of the following?
« Reply #7 on: March 25, 2013, 09:12:48 PM »
That is correct.
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #8 on: March 25, 2013, 09:16:36 PM »
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #9 on: March 25, 2013, 09:17:53 PM »
Quote from: discodermolide on March 25, 2013, 09:12:48 PM
That is correct.

Oh no :(

It says it's wrong...
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Offline discodermolide

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Re: Draw the major organic product of the following?
« Reply #10 on: March 25, 2013, 09:20:47 PM »
Well the condensation of two equivalents of this ester should give
CCCC(C(CC)C(OCC)=O)=O
I suppose you could also get this
CCCC(C(C(CCC)=O)(CC)C(OCC)=O)=O
as the middle hydrogen of the first product is then the most acidic one.
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #11 on: March 25, 2013, 09:23:27 PM »
Quote from: discodermolide on March 25, 2013, 09:20:47 PM
Well the condensation of two equivalents of this ester should give
CCCC(C(CC)C(OCC)=O)=O

Idk :(
I've used 3/3 submissions for that one...

So I suppose species B isn't CC[O-]?
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Offline discodermolide

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Re: Draw the major organic product of the following?
« Reply #12 on: March 25, 2013, 09:26:48 PM »
Sorry I added a bit to my last post.
I think B could be ethoxide.
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Offline theanonymous

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Re: Draw the major organic product of the following?
« Reply #13 on: March 25, 2013, 09:30:25 PM »
Quote from: discodermolide on March 25, 2013, 09:26:48 PM
Sorry I added a bit to my last post.
I think B could be ethoxide.

Species B isn't ethoxide :(
I hate Webassign...
3/3 submissions used for species B...

No hope for the last one.
I have to wait until tomorrow morning at 9:45 AM to see the answers/if your answers were close :(

What about number 6? You said that it's not like the other reactions?
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Offline discodermolide

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Re: Draw the major organic product of the following?
« Reply #14 on: March 25, 2013, 09:34:49 PM »
Sorry I was referring to one of your previous posts. The images are a bit small on my screen and with my eyesight!
Let me think about number 6.
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