Quick Guide to Organic NomenclatureO

OO

O

OH

O

acetic acid diethyl etheror

ethyl etheror

ether

OH

ethanolor

ethyl alcoholor

alcoholor

hooch

acetone ethyl acetate

benzene

CO2H OMe CO2H

O

O

OHO

HOOH

OHHO

O

N

N

O

O

OCH3

O

H2N NH2

toluene benzoic acid anisole aspirin DEET

glucose cocaine sildenafil

RDX

cadaverine

caffeine

amoxicillin

CH4

CH3CH3

methane

ethane

propane

butane

pentane

hexane

heptane

octane

nonane

decane

undecane

dodecane

CH3OH

CH3CH2OH

methanol

ethanol

1-propanolor

propan-1-olor

n-propanolor

n-propyl alcohol

OH

OH

2-propanolor

iso-propanolor

iso-propyl alcohol

No compounds with the same name!

1-undecanol

2-undecanol

5-undecanol

OH

OHOH

OH5-undecanol

Pick longest carbon chain as base, assign numbers so that they are as low as possible

Are two compounds the same?Can they be “superimposed”?

Yes same compound

No different compounds

OH

OH

OH

OH

Are two compounds the same?OH

OH

OH

OH

Neither of these can be superimposed with any of the others

Therefore, each is different from one another and from the other two.

Flip over - same structure

Therefore, these are the same compound

All have the same molecular formula (C11H24O).

Therefore, the different compounds are structural isomers.

More complex alkanes1. Pick longest carbon chain as base (or, perhaps, cycloalkane or aromatic).2. Determine substituents; assign numbers so that you have the lowest set of numbers.3. Name is list of substituents in alphabetical order, preceeded by number.

Cl

F

More complex alkanes1. Pick longest carbon chain as base (or, perhaps, cycloalkane or aromatic).2. Determine substituents; assign numbers so that you have the lowest set of numbers.3. Name is list of substituents in alphabetical order, preceeded by number.

Cl

F Longest carbon chain = 8 : thus, it is an octane

Substituents: methyl, chloro, fluoro

Either 2, 5, 6 or 3, 4, 7 – go with 2, 5, 6

5-chloro-6-fluoro-2-methyloctane

All numbers and letters separated by dash.

NH2

Chain = 9: nonane

Base = nonylamine (NH2 – amine)

Substituents: 2 methyls

3,5-dimethyl-5-nonylamine

Chain = not applicable

Base = cyclohexanol (6 membered ring of carbons)

Substituents: bromo, amino, isopropyl

3-amino-2-bromo-5-isopropylcyclohexanol

HO NH2

Br

CH4

CH3CH3

methane

ethane

propane

butane

pentane

hexane

heptane

octane

nonane

decane

undecane

dodecane

CH4

CH2=CH2 ethene

propene

1-butene

2-pentene

3-hexene

3-heptene

1-octene

3-nonene

5-decene

4-undecene

dodec-3-ene

Cl OH

Chain = 12: dodecaneAlkene dodeceneBase = dodecenol (alcohol)

Substituents: chloro, phenyl (benzene ring), n-propyl

4-chloro-7-phenyl-6-n-propyldodec-3-en-2-ol