Carboxylic Acids and Their Derivatives

by Adam Le Gresley, PhD

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    Related to the carbonyl functional group we discussed in the last lecture, I’d now like to introduce you to carboxylic acids and their derivatives; the derivates being, again, increasingly more useful from a synthetic perspective, as we will see. Carboxylic acids, as you can see on the board, have the general structure shown here where you have an R group which can be alkyl or aryl attached to a carbonyl and on that same carbon, that carbonyl carbon you have an OH group attached. This imparts an acidic quality as we will see and hence, the term as carboxylic acids. In this particular case, when you are using the… considering the nomenclature from an IUPAC perspective, what you do is you take away the “-e” at the end of the corresponding alkane and then you replace it with “-oic acid”. So, for example, in the case of a 2 carbon system ethane, we remove the “–e” and it is ethanoic acid. In the case of a 3 carbon system, including the carbonyl carbon such as propane, we would then call propanoic acid and butanoic, pentanoic and so on and so forth. Examples as I said are ethanoic acid which is otherwise known as acetic acid and here, the substitution nomenclature is also the same. Note that the carbonyl carbon has the priority and therefore, when you count back 1, 2, 3, 4, 5 to where the two substituents are you will call this 5,5-dimethylhexanoic acid. Always remember that the carbonyl carbon counts as that carbon. So, when you are looking at the chain, it is not a pentanoic acid, rather it is a hexanoic acid. So, we talked about acidity and acitum bases back in Module II and I’d briefly discussed the idea of induction and how this can improve...

    About the Lecture

    The lecture Carboxylic Acids and Their Derivatives by Adam Le Gresley, PhD is from the course Organic Chemistry. It contains the following chapters:

    • Carboxylic acids and their derivatives
    • Structure and acidity
    • Nomenclature
    • Nucleophilic substitution
    • Reactivity of carboxylic acids
    • Hydrolysis
    • Amides formation from esters
    • Exercise

    Included Quiz Questions

    1. benzaldehyde
    2. benzoic acid
    3. benzyl chloride
    4. benzophenone
    5. None of the above

    Author of lecture Carboxylic Acids and Their Derivatives

     Adam Le Gresley, PhD

    Adam Le Gresley, PhD

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