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 compounds

Carboxylic acids
Anhydrides
Esters
Acyl Halides
Amides
Nitriles
Aldehydes
Ketones
Alcohols
Thiols
Amines
Ethers
Sulfides
Alkenes
Alkynes
Halides
Nitro
Alkanes
Aromatic compounds
Bicyclic compounds
Heterocyclic compounds
Carbohydrates
Amino acids
Lipids
Polymers
Radicals
Organometallic compounds
The rules of systematic nomenclature is based on functional

group priority.
Why organic nomenclature exists?

Nomenclature of compounds should contain within itself an
explicit or implied relationship to the compound.
antipyretic drug
explosive material
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 explosives
3. 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.
2.
3.
4.
propranolol: (RS)-1-(1-methylethylamino)-3-(1-naphthyloxy)propan-2-ol
Adenosine triphosphate
Purines and pyrimidines
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 -ane
Substituent: Greek prefix + suffix -yl
Abbreviations: Me, Et, Pr, Bu

Arranging substituents: alphabetize (ignore greek prefixes, except iso)
10- dec
11- undec
12- dodec
13- tridec
14- tetradec
20- eicos
30- triacont
40- tetracont
100- hect
1. Cyclic alkanes: cyclo-

2. Ring=parent if # of C in ring># of C in linear chain
3. Complex substituents
note: sec-pentyl
Haloalkanes, Nitroalkanes & Azides
Halides, nitro & azido groups are always treated as

substituents.
1. haloalkane: alkyl halide

2. nitroalkane: prefix nitro-
3. azides: prefix azido-, or alkyl azide
Haloalkanes, Nitroalkanes & Azides
1. perfluoro-, perchloro-, perbromo-, periodo2. chloroform, fluoroform, iodoform, bromoform

3. nitrosobenzene
Alkenes (RC=CR) & Alkynes (RCCR)
if as substituent:
1. alkene=alkenyl
2. alkyne=alkynyl
Alkenes (RC=CR) & Alkynes (RCCR)
1. acetylene, methylacetylene
2. ethylene, propylene, isobutene, isoprene, allene
3. vinyl, allyl, phenyl, methylene
Note: vinyl halide, allyl halide, allyl amine, cumulene (butatriene)
Ethers (ROR) & Sulfides (RSR)
1. simple thioethers: alkyl alkyl sulfide

2. 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 oxide

1. 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 substituent
3. ring system (oxirane, oxetane, oxolane/tetrahydrofuran, oxane): n-alkyl-n-alkyloxirane (n
are locants in the parent ring)
peroxides:
as suffix: peroxide
as prefix: peroxy-
Amines (R3N)
1. alkylamine
2. alkanamine
Secondary amines: N-alkylalkylamine or N-alkylalkanamine (other one treated as substituent)
Tertiary amines: N,N-alkylalkylalkylamine or N,N-alkylalkylalkanamine
prefix: amino
diamines: 1,2-ethyldiamine
N,N,N-trimethyl-1,2-ethyldiamine
N,N,1-trimethyl-1,3-propylamine
Thiols (RSH)
1. n-alkanethiol/alkane-n-thiol
2. as prefix: sulfanyl/mercapto
Alcohols (ROH)
1. alkyl alcohol
2. alkanol
prefix: hydroxy
Ketones (R(C=O)R)
1. alkyl alkyl ketone

2. n-alkanone/alkan-n-one
note: n,n-alkanedione
prefix: oxo
Aldehydes (R(C=O)H)
1. alkanal
as prefix: oxo- or formyl-
common names: formaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, valeraldehyde
Nitriles (RCN)
1. alkanenitrile/-onitrile
2. cyanoalkane (for simpler alkyl groups, treated as substituent)
as prefix: cyano-
isocyanide: phenyl isocyanide (suffix)
isocyanato: prefix
Amides (R(C=O)NR2)
1. alkanamide
2. if N is substituted: N-alkylalkanamide
Acyl Halides (R(C=O)X)
1. acyl halide
2. alkanoyl halide
as 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

Organic Nomenclature

Încărcat de

Informații document

Drepturi de autor

Formate disponibile

Partajați acest document

Partajați sau inserați document

Opțiuni de partajare

Vi se pare util acest document?

Este necorespunzător acest conținut?

Drepturi de autor:

Formate disponibile

Organic Nomenclature

Încărcat de

Drepturi de autor:

Formate disponibile

Organic Nomenclature

Wednesday, April 24, 13

Howard Zimmerman - professor of chemistry at University of Wisconsin-Madison, published

There are so many organic compounds

The rules of systematic nomenclature is based on functional

Wednesday, April 24, 13

Why organic nomenclature exists?

Wednesday, April 24, 13

1. paracetamol: N-(4-hydroxyphenyl)ethanamide: N-(4-hydroxyphenyl)acetamide

Name of organic compounds varies depending