Transcription of Ketones and Aldehydes - Rutgers University
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Ketones and Aldehydes - Rutgers University
Ch18 Ketones and Aldehydes (landscape) Page 1 Ketones and Aldehydes The carbonyl group is of central importance in organic chemistry because of its ubiquity. Without studying the carbonyl group in depth we have already encountered numerous examples of this functional group ( Ketones , Aldehydes , carboxylic acids, acid chlorides, etc). The simplest carbonyl compounds are Aldehydes and Ketones . A ketone has two alkyl (or aryl) groups bonded to the carbonyl carbon. An aldehyde has one alkyl (or aryl) group and one hydrogen bonded to the carbonyl carbon. Structure of the carbonyl group The carbonyl carbon is sp2 hybridized, and has a partially filled unhybridized p orbital perpendicular to the framework. RCHORCRO aldehydeketone Ch18 Ketones and Aldehydes (landscape) Page 2 The oxygen is also sp2 hybridized, with the 2 lone pairs occupying sp2 orbitals. This leaves one electron in a p orbital. These p orbitals form the carbon oxygen bond. The C=O double bond is like a C=C double bond except the carbonyl double bond is shorter and stronger.
The dithiane anion can react as a nucleophile with primary alkyl halides, and this alkylation generates a thioacetal. The hydrolysis of a thioacetal generates an aldehyde. Alternatively, the thioacetal can be further deprotonated and reacted with another (different) alkyl halide to generate a new thioacetal with two alkyl substituents.
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