有机化学第九章1.ppt

Chapter 9Aldehydes and Ketones: Nucleophilic Addition Reaction. The nucleophilic addition of water to aldehydes and ketones is slow in pure water but is catalyzed by both acid and base. As always, the catalyst doesnt change the position of the equilibrium; it affects only the rate at which the hydration reaction occurs. * In this and the next two chapters, well discuss the most important and widely occurring functional group in both organic and biological chemistry-the carbonyl group, C=O. Carbonyl compounds are everywhere in nature. Most biologically important molecules contain carbonyl groups. 9.1 The Nature of Carbonyl Compounds Its useful to classify carbonyl compounds into two general categories based on the kinds of chemistry they undergo. The -H and -R in these compounds cant act as leaving groups in substitution reactions. The -OH, -OR, -Cl, -NH2, and -OCOR in these compounds can act as leaving groups in substitution reactions. The carbon-oxygen double bond of carbonyl groups is similar in some respects to the carbon-carbon double bond of alkenes. The oxygen also has two nonbonding pairs of electrons, which occupy its remaining two orbitals. Electronic structure of the carbonyl group polarized 9.2 Naming Aldehydes and Ketones Aldehydes are named by replacing the terminal -e of the corresponding alkane name with -al. The parent chain must contain the -CHO group, and the -CHO carbon is always numbered as carbon 1. 2-Ethyl-4-methylpentanal Propanal (Propionaldehyde) Ethanal (Acetaldehyde) For more complex aldehydes in which the -CHO group is attached to a ring, the suffix -carbaldehyde is used: Cyclohexanecarbaldehyde 2-Naphthalenecarbaldehyde Some simple and well-known aldehydes also have common names. √ √ √ Ketones are named by replacing the terminal -e of the corresponding alkane name with -one. The parent chain is the longest one that contains the ketone group, and numbering begins at the end neare