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  Reactions at the a-Carbon Homework Help - K-12 Grade Level, College Level Chemistry

Introduction to Reactions at the α-Carbon

Many aldehydes and ketones go through substitution reactions at an alpha carbon, as displayed in the diagram below (alpha-carbon atoms are colored blue). These reactions are acid or base catalyzed but in the example of halogenation the reaction makes an acid as one of the results, and so is autocatalytic. If the alpha-carbon is a chiral center, as in the second instance, the results of halogenation and isotopic exchange are racemic. Certainly, treatment of this ketone reactant with acid or base only serves to racemize it. Not all carbonyl compounds depict these features, the third ketone being an instance.

Two significant conclusions may be take place from these instances. First, these substitutions are limited to carbon atoms alpha to the carbonyl group. The Cyclohexanone (the first ketone) has two alpha-carbons and four potential substitutions (the alpha-hydrogens). One or all four of these hydrogens might be substituted, but none of remaining six hydrogens on the ring react, Depending on the reaction conditions,. The second ketone verifies that fact, only the alpha-carbon going through substitution, in spite of the existence of several other sites. 2nd, the substitutions are limited to hydrogen atoms. This is illustrated convincingly by the third ketone, which is structurally identical to the second but has no alpha-hydrogen.

- It is now manifest that the carbon-oxygen double bond functionality (C=O) is general to various

Distinct classes of compounds:

- The chemistry of this ubiquitous functional group will now be re-examined, but at carbon

Adjacent to the C=O, that is, the alpha carbon (α-C)

- The aforementioned compounds go through substitution reactions at their alpha carbons with several

Electrophiles under the acidic or basic conditions

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