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Explanation of why alcohols and carboxylic acids tent to react with each other. Watch

    • Thread Starter

    If anyone can help me out with this question I would appreciate it.

    Explain why an alcohol and a carboxylic acid tend to react with each other. You should use the terms nucleophile, electronegativity, polar bond, delta positive, delta negative and lone pair of electrons.

    Honest answer, in a neutral solution they generally won’t react but my advice would be for you to think about the polarity of the C=O bond and the C-O bond in the alcohol and see if you can see how they might fit together.

    I would start this by thinking about the actual structure of the groups you are analysing,

    The alcohol:


    The Carboxylic acid:


    . Now consider which group has more electron withdrawing substituents (negative inductive effect (-I)).

    -) We can obviously see that the (-I) substituents are the Oxygens, that are extremely electronegative. The carboxylic acid has two of them, so therefore, two are going to be withdrawing electric charge from the carbon in C=O.

    So this particular carbon will be made extremely D++ (delta Positive).

    . The Alcohol group also has a polar bond since oxygen is more delta negative than the carbon. It has a lone pair of electrons. Since the carbonyl group has been made extremely d++ (or electrophilic), the lone pair of electrons on the R-O-H allow the alcohol to act as a nucleophile. It therefore can attack the carbonyl in a Nucleophilic addition-style reaction.

    Something like that.

    Please note that while this is a nice way of modelling the reaction, it doesn't explain in full detail how this reaction actually works.

    You actually require an Acid catalyst in order to make the carbonyl group electrophilic enough to allow for a 1,2 nucleophilic addition to occur, which is followed by a proton transfer and subsequent deprotonation at the end.

    This is actually called the fisher esterification and I'd highly recommend you read about it here to gain a more fundamental understanding that will serve you well if you go on to study higher level synthetic reactions (like the Aldol condensation).

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