A Nomenclature of Polyfunctional Organic Compounds

Appendix A Nomenclature of Polyfunctional Organic Compounds A-1 Appendix B Acidity Constants for Some Organic Compounds A-8 Appendix C Glossary A-10 Appendix D Answers to In-Text Problems A-30... 

Many organic compounds contain more than one functional group. When one of those functional groups is halo (X-) or alkoxy (RO-), these groups are named as substituents as described in Sections 7.2 and 9.3B. To name other polyfunctional compounds, we must learn which functional group is assigned a higher priority in the rules of nomenclature. Two steps are usually needed ... 

A polyfunctional organic molecule can contain many different kinds of functional groups, but for nomenclature purposes, we must choose just one suffix. It s not correct to use two sufhxes. Thus, keto ester 3 must be named either as a ketone with an -one. suffix or as an ester with an -oate suffix but can t be named as an -onoate. Similarly, amino alcohol 4 must be named either as an alcohol (-ol) or as an amine i-amine) but can t properly be named as an -olamine. The only exception to this rule is in naming compounds that have double or triple bonds. For example, the unsaturated acid H2C=CHCH2C00H is 3-butenoic acid, and the acetylenic alcohol HCSCCH2CH2CH2CH2OH is 5-hexyn-l-ol. 

Judging from the number of incorrect names that appear in the chemical literature, it s probably safe to say that relatively few practicing organic chemists are fully conversant with the rules of organic nomenclature. Simple hydrocarbons and monofunctional compounds present few difficulties because the basic rules for naming such compounds are logical and easy to understand. Problems, however, are often encountered with polyfunctional compounds. Whereas most chemists could correctly identify hydrocarbon 1 as 3-ethyl-2,5-dimethylheptane, rather few could correctly identify poly functional compound 2. Should we consider 2 as an ether As an ethyl ester As a ketone As an alkeae It is, of course, all four, but it has only one correct name ethyl 3-(4-methoxy-2-oxo-3-cyclohexenyl)propanoate. 

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