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基础有机化学-醛和酮
2012-12-17 09:22:50 来源:有机化学网 浏览:89343

Aldehydes and Ketones

1. Nomenclature of Aldehydes and Ketones

Aldehydes and ketones are organic compounds which incorporate a carbonyl functional group, C=O. The carbon atom of this group has two remaining bonds that may be occupied by hydrogen or alkyl or aryl substituents. If at least one of these substituents is hydrogen, the compound is an aldehyde. If neither is hydrogen, the compound is a ketone.

The IUPAC system of nomenclature assigns a characteristic suffix to these classes, al to aldehydes and one to ketones. For example, H2C=O is methanal, more commonly called formaldehyde. Since an aldehyde carbonyl group must always lie at the end of a carbon chain, it is by default position #1, and therefore defines the numbering direction. A ketone carbonyl function may be located anywhere within a chain or ring, and its position is given by a locator number. Chain numbering normally starts from the end nearest the carbonyl group. In cyclic ketones the carbonyl group is assigned position #1, and this number is not cited in the name, unless more than one carbonyl group is present. If you are uncertain about the IUPAC rules for nomenclature you should review them now.
Examples of IUPAC names are provided (in blue) in the following diagram. Common names are in red, and derived names in black. In common names carbon atoms near the carbonyl group are often designated by Greek letters. The atom adjacent to the function is alpha, the next removed is beta and so on. Since ketones have two sets of neighboring atoms, one set is labeled α, β etc., and the other α', β'etc.

Very simple ketones, such as propanone and phenylethanone (first two examples in the left column), do not require a locator number, since there is only one possible site for a ketone carbonyl function. Likewise, locator numbers are omitted for the simple dialdehyde at the bottom left, since aldehyde functions must occupy the ends of carbon chains. The hydroxy butanal and propenal examples (2nd & 3rd from the top, left column) and the oxopropanal example (bottom right) illustrate the nomenclature priority of IUPAC suffixes. In all cases the aldehyde function has a higher status than either an alcohol, alkene or ketone and provides the nomenclature suffix. The other functional groups are treated as substituents. Because ketones are just below aldehydes in nomenclature suffix priority, the "oxo" substituent terminology is seldom needed.
Simple substituents incorporating a carbonyl group are often encountered. The generic name for such groups is acyl. Three examples of acyl groups having specific names are shown below.

 

2. Occurrence of Aldehydes and Ketones

Natural Products

Aldehydes and ketones are widespread in nature, often combined with other functional groups. Example are shown in the following diagram. The compounds in the top row are found chiefly in plants or microorganisms; those in the bottom row have animal origins. With the exception of the first three compounds (top row) these molecular structures are all