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10: Nucleophilic Carbonyl Addition Reactions

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    • 10.1: Prelude to Nucleophilic Carbonyl Addition Reactions
      Acetals are derived from aldehydes. The reactions that occur at the carbonyl carbon of aldehydes and ketones is absolutely central to the chemistry of carbohydrates such as starch and cellulose, and it is this chemistry that is the subject of the chapter we are about to begin.
    • 10.2: Nucleophilic Additions to Aldehydes and Ketones - An Overview
      Recall from chapter 1 that the ketone functional group is made up of a carbonyl bonded to two carbons, while in an aldehyde one (or both) of the neighboring atoms is a hydrogen.
    • 10.3: Hemiacetals, Hemiketals, and Hydrates
      One of the most important examples of a nucleophilic addition reaction in biochemistry, and in carbohydrate chemistry in particular, is the addition of an alcohol to a ketone or aldehyde. When an alcohol adds to an aldehyde, the result is called a hemiacetal; when an alcohol adds to a ketone the resulting product is a hemiketal.
    • 10.4: Acetals and Ketals
      Hemiacetals and hemiketals can react with a second alcohol nucleophile to form an acetal or ketal. The second alcohol may be the same as the first (ie. if R2=R3 in the scheme below), or different.
    • 10.5: N-glycosidic Bonds
      We have just seen that when a second alcohol attacks a hemiacetal or hemiketal, the result is an acetal or ketal, with the glycosidic bonds in carbohydrates providing a biochemical example. But if a hemiacetal is attacked not by a second alcohol but by an amine, what results is a kind of ‘mixed acetal’ in which the anomeric carbon is bonded to one oxygen and one nitrogen.
    • 10.6: Imines
      The electrophilic carbon atom of aldehydes and ketones can be the target of nucleophilic attack by amines as well as alcohols. The end result of attack by an amine nucleophile is a functional group in which the C=O double bond is replaced by a C=N double bond, and is known as an imine.
    • 10.7: A Look Ahead - Addition of Carbon and Hydride Nucleophiles to Carbonyls
      We have seen in this chapter a number of reactions in which oxygen and nitrogen nucleophiles add to carbonyl groups. Other nucleophiles are possible in carbonyl addition mechanisms: in chapters 12 and 13, for example, we will examine in detail some enzyme-catalyzed reactions where the attacking nucleophile is a resonance stabilized carbanion (usually an enolate ion).
    • 10.E: Nucleophilic Carbonyl Addition Reactions (Exercises)
    • 10.S: Nucleophilic Carbonyl Addition Reactions (Summary)