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iupac nomenclature of organic chemistry - Sciensage.info

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Page8<br />

Esters<br />

Esters (R-CO-O-R') are named as alkyl derivatives <strong>of</strong> carboxylic acids. The alkyl (R') group is named<br />

first. The R-CO-O part is then named as a separate word based on the carboxylic acid name, with the<br />

ending changed from -oic acid to -oate. For example, CH 3 CH 2 CH 2 CH 2 COOCH 3 is methyl pentanoate, and<br />

(CH 3 ) 2 CHCH 2 CH 2 COOCH 2 CH 3 is ethyl 4-methylpentanoate. For esters such as ethyl acetate<br />

(CH 3 COOCH 2 CH 3 ), ethyl formate (HCOOCH 2 CH 3 ) or dimethyl phthalate that are based on common<br />

acids, IUPAC recommends use <strong>of</strong> these established names, called retained names. The -oate changes to<br />

-ate.<br />

If the alkyl group is not attached at the end <strong>of</strong> the chain, the<br />

bond position to the ester group is infixed before "-yl":<br />

CH 3 CH 2 CH(CH 3 )OOCCH 2 CH 3 may be called but-2-yl<br />

propanoate or but-2-yl propionate.<br />

Amines and Amides<br />

Amines (R-NH 2 ) are named for the attached<br />

alkane chain with the suffix "-amine" (e.g.<br />

CH 3 NH 2 methanamine). If necessary, the<br />

bonding position is infixed: CH 3 CH 2 CH 2 NH 2<br />

propan-1-amine, CH 3 CHNH 2 CH 3 propan-2-<br />

amine. The prefix form is "amino-".<br />

For secondary amines (<strong>of</strong> the form R-NH-R), the longest carbon chain attached to the nitrogen atom<br />

becomes the primary name <strong>of</strong> the amine; the other chain is prefixed as an alkyl group with location<br />

prefix given as an italic N: CH 3 NHCH 2 CH 3 is N-methylethanamine. Tertiary amines (R-NR-R) are treated<br />

similarly: CH 3 CH 2 N(CH 3 )CH 2 CH 2 CH 3 is N-ethyl-N-methylpropanamine. Again, the substituent groups are<br />

ordered alphabetically.

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