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  1. #1
    In the clinch Semtex's Avatar
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    Chemistry Question for chem majors regarding aldol condensation (7k reps)(srs)

    We did a lab on aldol condensation where we basically reacted benzaldehyde + acetone with NaOH to create dibenzalacetone. We calculated the limiting reactant and whatnot but there are a couple questions on the hand out I don't know how to answer.

    1) Draw the structure of the expected product of the aldol condensation of 4-methylbenzaldehyde and acetonphenone.

    2) A possible side product of the reaction is self-condensation of acetone. Draw the structure of this side product. Explain how the experimental procedure is setup to minimize the formation of the side product.

    I don't even know how to answer these questions. 7k reps for some help brahs.
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  2. #2
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    Hey bro, can you make me MDMA, LSD and mescaline?

    I see that you're in California.
    For every neg that I get I will get repped tenfold.

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  3. #3
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    Originally Posted by Semtex View Post
    We did a lab on aldol condensation where we basically reacted benzaldehyde + acetone with NaOH to create dibenzalacetone. We calculated the limiting reactant and whatnot but there are a couple questions on the hand out I don't know how to answer.

    1) Draw the structure of the expected product of the aldol condensation of 4-methylbenzaldehyde and acetonphenone.

    2) A possible side product of the reaction is self-condensation of acetone. Draw the structure of this side product. Explain how the experimental procedure is setup to minimize the formation of the side product.

    I don't even know how to answer these questions. 7k reps for some help brahs.
    Sounds like Chemistry for arts and science majors to me...
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  4. #4
    Registered User fecalneek's Avatar
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    i did this lab a few weeks ago. give me a minute, i'll try the 1st question.
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  5. #5
    In the clinch Semtex's Avatar
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    Originally Posted by Zestos View Post
    Hey bro, can you make me MDMA, LSD and mescaline?

    I see that you're in California.
    Originally Posted by TheCon View Post
    Sounds like Chemistry for arts and science majors to me...
    thanks for respecting the srs tag dip****s
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  6. #6
    In the clinch Semtex's Avatar
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    Originally Posted by littlenpup View Post
    i did this lab a few weeks ago. give me a minute, i'll try the 1st question.
    thanks brah.

    i missed the introduction to this lab so im kind of out of the loop.
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  7. #7
    Registered User Zestos's Avatar
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    Originally Posted by Semtex View Post
    thanks for respecting the srs tag dip****s
    I'm serious, PM me bro.
    For every neg that I get I will get repped tenfold.

    [Official] San Diego Brah
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  8. #8
    17 now brah Starred's Avatar
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    I don't know da answerz but I'm guessing number 2 iinvolves the use of NaOH instead of water so no backwards reaction can occur.
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  9. #9
    in on this Jaxy_Waxy's Avatar
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    I think I did these right... I hope I did these right. IIRC you just take the C=O of one molecule, change it to a C=C and attach it to the alpha carbon of the other molecule.

    cross-condensation of 4-methylbenzaldehyde and acetophenone:


    self-condensation of acetone:
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  10. #10
    In the clinch Semtex's Avatar
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    thx man im going to hope for more answers to confirm but reps nonetheless
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  11. #11
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    To be effective, you must view the acetone as an anonode. Then the strings of particles that will result will effect the methodyzime and fok you in you butt you stupid you read up to here.
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    this is how i did it



    lmao i know it looks ugly as **** but i think the general order of how its attached it correct. if it's not....oh well

    to the above guy^ one of your C=O groups is supposed to turn into OH so I don't think that's right. you're making an aldol, which is one alcohol and one aldehyde.
    Last edited by littlenpup; 04-26-2010 at 02:03 PM.
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  13. #13
    in on this Jaxy_Waxy's Avatar
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    Originally Posted by littlenpup View Post
    this is how i did it



    lmao i know it looks ugly as **** but i think the general order of how its attached it correct. if it's not....oh well

    to the above guy^ one of your C=O groups is supposed to turn into OH so I don't think that's right. you're making an aldol, which is one alcohol and one aldehyde.
    ah, yeah I included a dehydration to remove an H2O and make the alpha, beta unsaturated molecule. The saturated should be like this:

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  14. #14
    In the clinch Semtex's Avatar
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    Originally Posted by Jaxy_Waxy View Post
    I think I did these right... I hope I did these right. IIRC you just take the C=O of one molecule, change it to a C=C and attach it to the alpha carbon of the other molecule.

    cross-condensation of 4-methylbenzaldehyde and acetophenone:


    self-condensation of acetone:
    btw did you use a program to create the line structures or did you just get that off a website?

    Originally Posted by littlenpup View Post
    this is how i did it



    lmao i know it looks ugly as **** but i think the general order of how its attached it correct. if it's not....oh well

    to the above guy^ one of your C=O groups is supposed to turn into OH so I don't think that's right. you're making an aldol, which is one alcohol and one aldehyde.
    reps for trying
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  15. #15
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    Originally Posted by Jaxy_Waxy View Post
    I think I did these right... I hope I did these right. IIRC you just take the C=O of one molecule, change it to a C=C and attach it to the alpha carbon of the other molecule.

    cross-condensation of 4-methylbenzaldehyde and acetophenone:


    self-condensation of acetone:
    These are the correct structures for what the question asked.

    Specifically, in Acetone, there are 2 alpha-carbons, so one could see if you made the structure for the self acetone-aldol, it still leaves an alpha carbon open to become an enolate and do another aldol, basically making a long chain. The experiment you did used a compound that only has one alpha carbon in order to make sure this does not happen.

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  16. #16
    in on this Jaxy_Waxy's Avatar
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    Originally Posted by Lowporkwa View Post
    These are the correct structures for what the question asked.

    Specifically, in Acetone, there are 2 alpha-carbons, so one could see if you made the structure for the self acetone-aldol, it still leaves an alpha carbon open to become an enolate and do another aldol, basically making a long chain. The experiment you did used a compound that only has one alpha carbon in order to make sure this does not happen.

    (Graduate student, TA for Organic Chem)
    Ah good, that's a relief cause I have an exam on aldol and Claisen condensations in a week
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  17. #17
    Supercritical Lowporkwa's Avatar
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    Originally Posted by Jaxy_Waxy View Post
    Ah good, that's a relief cause I have an exam on aldol and Claisen condensations in a week
    Just study the mechanisms. Claisen and Aldol are pretty much the same thing. They are not complicated once you really start to see them and get used to them. They are very important in devising retrosynthetic problems (which professors LOVE to make you do). Get them and look for them on every synthesis problem you get!! My boss LOVES to put those on tests.
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