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Organic Chemistry: Reactivity levels

  1. Apr 27, 2009 #1
    This is a general Organic Chemistry question. How do the reactivities of the following compare?

    Acyl Chlorides, Esters, Anhydrides, Amides, Ketones, Aldehydes

    3. The attempt at a solution

    I know the following "ladder:"

    MOST REACTIVE

    acyl chloride
    anhydride
    ester
    amide

    LEAST REACTIVE


    I know also that aldehydes are more reactive than ketones. However, where do those two fit in according to the ladder layout?

    Thank you!
     
  2. jcsd
  3. Apr 28, 2009 #2

    chemisttree

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    Well acetone is certainly less reactive than an amide.
     
  4. Apr 28, 2009 #3
    It really depends what type of reaction you're considering. Simple nucleophilic addition to the carbonyl vs acyl substitution.
     
  5. Apr 28, 2009 #4
    Well the reactions we've been doing have concerned creating amides, reducing them, and reactions with carboxylic acids. Mostly substitution/elimination stuff, I suppose. This also falls in line with Gabriel synthesis, Mannich reactions, etc.

    Is there not just a general rule here?
     
  6. Apr 28, 2009 #5
    Well, if you're considering a substitution at a carbonyl, or more specifically, a beta elimination driven by carbonyl reformation. It's a good idea to look at the Pka of the leaving groups.
    R- ~ 50
    NH2 ~ 35
    RO- ~ 16
    RCO2- ~ 5
    Cl- ~ -7

    On the other hand, if you're just considering nucleophilic addition to the carbonyl, then electronic and steric effects are what you compare.
     
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