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Topic: A couple of carbondyl and aromatic questions.  (Read 24467 times)

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Offline orgopete

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Re: A couple of carbondyl and aromatic questions.
« Reply #45 on: May 19, 2012, 04:30:20 AM »
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@Twickel, As frustrating as you are finding the chemistry, we are finding a similar frustration. I used to advise students to number the atoms to avoid making a wrong connection. In one of your posts, you have indeed numbered your starting material and yet failed to draw the correct product. For me, that is frustrating.

For your last problem, I could say to eliminate the weakest base, but with the structure so sloppily drawn, I am not sure what might be the result. If it is the result of a correctly drawn intermediate, it would be the correct product (to that point).
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Offline discodermolide

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Re: A couple of carbondyl and aromatic questions.
« Reply #46 on: May 19, 2012, 05:07:35 AM »
(Quote is link to reply #43)
@Twickel, As frustrating as you are finding the chemistry, we are finding a similar frustration. I used to advise students to number the atoms to avoid making a wrong connection. In one of your posts, you have indeed numbered your starting material and yet failed to draw the correct product. For me, that is frustrating.

For your last problem, I could say to eliminate the weakest base, but with the structure so sloppily drawn, I am not sure what might be the result. If it is the result of a correctly drawn intermediate, it would be the correct product (to that point).


I'm not sure Mr Twickel knows what the weakest base is. He is panicking and making errors. He needs to slow down and think.
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Offline Twickel

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Re: A couple of carbondyl and aromatic questions.
« Reply #47 on: May 19, 2012, 05:40:04 AM »
Ok, yes I have been drawing my products poorly I guess I am rushing too much and this is effecting my thinking, getting anxious because we have only had lectures on carbonyl chemistry, we have no tutorials ( do not know why) the tuts jumped straight from aromatics to quantam chemistry. This is also my first ever organic chem course I have taken.



So I formed the tetrehedral product, I then lose OEt-, not sure if I am correct but I thought, the Oet- that has left the tetrehedral carbon is a strong enough base to remove a hydrogen alpha to the di carbonyls, this is the driving force of the reaction, but there is a step somewhere in which you can add alkyl halides via Sn2, let me try I will draw as neat as possible.

Offline Dan

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Re: A couple of carbondyl and aromatic questions.
« Reply #48 on: May 19, 2012, 05:53:52 AM »
Looks good, but you ought to draw out the mechanism for the hydrolysis/deprotection step for your class.

I will add a little to orgopete's comment: The most frustrating thing for me here was the fact that you were posting several different versions of the same question. For example, you posted 3 versions of Q1, and each version had different multiple choice answers. Only one of the versions you posted actually had the correct answer as an option, because you copied the question down incorrectly. Take your time, read the question twice, and be careful - it will save you time in the long run.
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Offline Twickel

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Re: A couple of carbondyl and aromatic questions.
« Reply #49 on: May 19, 2012, 06:15:45 AM »
Yes, I did not realise until you mentioned it today, will try to organise myself better in the future.

Thank you to everyone for all the help.

Offline discodermolide

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Re: A couple of carbondyl and aromatic questions.
« Reply #50 on: May 19, 2012, 06:47:22 AM »
Yes, I did not realise until you mentioned it today, will try to organise myself better in the future.

Thank you to everyone for all the help.



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Offline Twickel

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Re: A couple of carbondyl and aromatic questions.
« Reply #51 on: May 19, 2012, 07:07:03 AM »
Thanks for those diagrams, I print them fill them in and stick them to my notes.

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