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12.8: reacciones de sustitución de acilo con un carbono o hidruro nucleófilo

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  • Section 12.7: A look ahead: acyl substitution reactions with a carbon or hydride nucleophile

    Although we have seen many different types of nucleophilic acyl substitutions in this chapter, we have not yet encountered a reaction in which the incoming nucleophile is a carbanion or a hydride.  Recall that in the previous chapter on aldehydes and ketones, we also postponed discussion of nucleophilic carbonyl addition reactions in which a carbanion or a hydride is the nucleophile.  The reason for putting off these discussions is that these topics are both important enough and diverse enough to warrant their own dedicated chapters. 

    In the next chapter, we will see many carbonyl addition and acyl substitution reactions where the nucleophilic species is a stabilized carbanion.  Then in chapter 16, we will encounter many reactions in which a hydride plays the part of a nucleophile. In these chapters you will see how these two nucleophilic species are generated.  For now, see if you can predict the result of the following biochemical reactions.

    Exercise 12.10: predict the products of the following reactions, both of which are part of the biosynthesis of isoprenoid compounds such as cholesterol and lycopene:

    a) acetoacetyl CoA acetyltransferase


    b) HMG-CoA reductase