Organic Nomenclature

Organic Nomenclature CHEM 31.1

Wednesday, April 24, 13

Howard Zimmerman - professor of chemistry at University of Wisconsin-Madison, published hundred of papers in organic photochemistry, must among the most cited papers in the history of organic chemistry

There are so many organic compoundsCarboxylic acidsAnhydridesEstersAcyl HalidesAmidesNitrilesAldehydesKetonesAlcohols

ThiolsAminesEthersSulfidesAlkenesAlkynesHalidesNitroAlkanes

Aromatic compoundsBicyclic compoundsHeterocyclic compoundsCarbohydratesAmino acidsLipidsPolymersRadicalsOrganometallic compounds

The rules of systematic nomenclature is based on functional group priority.


Why organic nomenclature exists?

antipyretic drug explosive material

Nomenclature of compounds should contain within itself an explicit or implied relationship to the compound.

nonessential amino acid


1. paracetamol: N-(4-hydroxyphenyl)ethanamide: N-(4-hydroxyphenyl)acetamide-antipyretic drug, analgesic 2. TNT: 2,4,6-trinitrotoluene: 2-methyl-1,3,5-trinitrobenzene - standard measure of strengths of bombs and other explosives3. alanine: 2-aminopropanoic acid:

Name of organic compounds varies depending which is prioritize first

It is important to recognize that the rules of systematic nomenclature need not necessarily lead to a unique name for each compound, but must always lead to an unambiguous one.

Organic nomenclature is not restricted to the rules of IUPAC.


Because...

There are traditional, semi-systematic or trivial names, which are widely used for a core group of organic compounds.


1. propranolol: (RS)-1-(1-methylethylamino)-3-(1-naphthyloxy)propan-2-ol2. Adenosine triphosphate3. Purines and pyrimidines4. Sugars

Traditional names are indispensable


So what have we learned so far?- Name of organic compound must describe the structure completely. Preferably unique, but not necessary.

- Non-systematic names are indispensable (convert complex names to simpler ones).


Alkanes - the backbone

Parent chain: Greek prefix + suffix -aneSubstituent: Greek prefix + suffix -yl


Abbreviations: Me, Et, Pr, BuArranging substituents: alphabetize (ignore greek prefixes, except iso)10- dec11- undec12- dodec13- tridec14- tetradec20- eicos30- triacont40- tetracont100- hect



1. Cyclic alkanes: cyclo-2. Ring=parent if # of C in ring># of C in linear chain3. Complex substituents



note: sec-pentyl

Haloalkanes, Nitroalkanes & Azides

Halides, nitro & azido groups are always treated as substituents.


1. haloalkane: alkyl halide2. nitroalkane: prefix nitro-3. azides: prefix azido-, or alkyl azide

Haloalkanes, Nitroalkanes & Azides


1. perfluoro-, perchloro-, perbromo-, periodo-2. chloroform, fluoroform, iodoform, bromoform3. nitrosobenzene

Alkenes (RC=CR) & Alkynes (RCCR)


if as substituent:1. alkene=alkenyl2. alkyne=alkynyl

Alkenes (RC=CR) & Alkynes (RCCR)


1. acetylene, methylacetylene2. ethylene, propylene, isobutene, isoprene, allene3. vinyl, allyl, phenyl, methyleneNote: vinyl halide, allyl halide, allyl amine, cumulene (butatriene)

Ethers (ROR) & Sulfides (RSR)


1. simple thioethers: alkyl alkyl sulfide2. intermediate thioethers: n-akylthioalkane (treat alkylthio as substituent)3. complex thioethers: n-thioalkane (includes S)1. alkyl alkyl ether 2. n-alkoxyalkane (treat alkoxy as substituent)3. complex ethers: n-oxaalkane (O included in parent chain, n as location of O in chain)

Epoxides & Peroxides


1&2 applicable only for substituted oxiranes or epoxides/ethylene oxide1. n-alkene oxide: functional group treated similar to a double bond (n to determine location if not unambiguous)2. n-epoxyalkane: functional group treated as a substituent3. ring system (oxirane, oxetane, oxolane/tetrahydrofuran, oxane): n-alkyl-n-alkyloxirane (n are locants in the parent ring)peroxides: as suffix: peroxideas prefix: peroxy-

Amines (R3N)


1. alkylamine2. alkanamineSecondary amines: N-alkylalkylamine or N-alkylalkanamine (other one treated as substituent)Tertiary amines: N,N-alkylalkylalkylamine or N,N-alkylalkylalkanamineprefix: aminodiamines: 1,2-ethyldiamineN,N,N-trimethyl-1,2-ethyldiamineN,N,1-trimethyl-1,3-propylamine

Thiols (RSH)


1. n-alkanethiol/alkane-n-thiol2. as prefix: sulfanyl/mercapto

Alcohols (ROH)


1. alkyl alcohol2. alkanolprefix: hydroxy

Ketones (R(C=O)R)


1. alkyl alkyl ketone2. n-alkanone/alkan-n-onenote: n,n-alkanedioneprefix: oxo

Aldehydes (R(C=O)H)


1. alkanalas prefix: oxo- or formyl-common names: formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde

Nitriles (RCN)


1. alkanenitrile/-onitrile2. cyanoalkane (for simpler alkyl groups, treated as substituent)as prefix: cyano- isocyanide: phenyl isocyanide (suffix)isocyanato: prefix

Amides (R(C=O)NR2)


1. alkanamide2. if N is substituted: N-alkylalkanamide

Acyl Halides (R(C=O)X)


1. acyl halide2. alkanoyl halideas prefix: haloformyl-

Esters (RC(=O)R)


1. alkyl alkanoate

Anhydrides (RC(=O)OC(=O)R)


1. alkanoic anhydride

Carboxylic acids (RCOOH)


Aromatic Compounds


Aromatic compounds


Aromatic Compounds


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Organic Nomenclature