Organic Chemistry II For Dummies by John T. Moore

Author:John T. Moore
Language: eng
Format: epub
Publisher: John Wiley & Sons, Ltd.
Published: 2010-06-03T16:00:00+00:00

Taking Them a Step Further: Reactions of Aldehydes and Ketones

When considering the reaction of carbonyl groups, remember the polarity of the carbon-oxygen bond, the hybridization of the carbon atom (sp2), and the bond angles of the planar group. Figure 10-16 summarizes these features.

Figure 10-16: Important features to keep in mind when considering the reaction of carbonyl groups.

Strong reducing agents like sodium borohydride and lithium aluminum hydride are capable of reducing aldehydes to primary alcohols and ketones to secondary alcohols. The general reaction is the reverse of the reactions used to form aldehydes and ketones by the oxidation of primary and secondary alcohols, respectively (to review, see the earlier section “Oxidation reactions”). However, the mechanisms for reduction are different.

Nucleophilic attack of aldehydes and ketones

Figures 10-17 and 10-18 summarize the important reaction features of carbonyl chemistry. Remember that both of these processes are reversible, and note that the carbocation resonance structure is susceptible to nucleophilic attack.

Figure 10-17: Nucleophilic attack upon a carbonyl group.

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