Chemistry Nomenclature

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Nomenclature rules

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1. Find the longest continuous carbon chain to determine the base name.

2. If there is more than one way to get the longest chain, choose the chain with the most substituents.

3. Number the carbons starting on the end closest to the first substituent. If both ends are equally close, start with the end that gives the second substituent the lower number, then the third, etc.

4. If there is more than one way to number the chain to give the substituents the lowest possible numbers, give the lower number to the substituent beginning with the letter closer to 'A.'

5. List the substituents in alphabetical order. Ignore numerical prefixes and hyphenated prefixes (e.g. 'tert-', and 'sec-'), but consider 'iso-' and 'cyclo-' If there is a complex substituent, the first letter of its prefix is considered in alphabetizing, even if it is a 'di,' 'tri', etc.

6. Name the substituents attached to the chain using the chain number as the locator. For multiple substituents, use 'di-,' 'tri', 'tetra-', etc. and separate numbers from letters using hyphens. If there is more than one substituent at the same location, the location must be listed separately for each substituent, e.g. '2,2-dimethyl'

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Halide substituents

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fluro-

chloro-

bromo-

iodo-

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Numerical prefixes

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1: meth-

2: eth-

3: prop-

4: but-

5: pent-

6: hex-

7: hep-

8: oct-

9: non-

10: dec-

11: undec-

12: dodec-

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Sec- prefix

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Indicates bonding through the secondary carbon

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Iso- prefix

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Indicates that the carbon chain ends in a fork or fishtail

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Tert- prefix

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Indicates bonding through the central (or tertiary) carbon

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IUPAC names

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Enclosed in parentheses and alphabetized by the first letter of the substituent

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Alkene

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Functional group with a double bond

Suffix: "ene"

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Alkyne

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Functional group with a triple bond

Suffix: "yne"

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Ether

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Substituent containing oxygen with a carbon chain on either side (not considered a functional group)

Common name:

1) Longest carbon chain is named first

2) the carbon chain on the other side of the oxygen is named

3) Suffix: "ether"

E.g. "ethyl methyl ether"

IUPAC name:

1) The shorter carbon chain is listed as a substituent by using its prefix.

2) The word "oxy" is used to refer to the ether.

3) The longer carbon chain is named as the main chain.

E.g. "methoxyethane"

Example of ether: "-OCH3"

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Amine

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Functional group containing nitrogen bonded to a carbon chain on at least one side

Suffix: "amine"

Substituents of the nitrogen are located at position "N"

Amine group as a substituent: amino group

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Alcohol

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Functional group containing "OH"

Suffix: "-ol"

Alcohol as a substituent: hydroxy group

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Ketone

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Functional group containing a carbonyl (C=O) bonded to two carbon chains

Suffix: "-one"

Ketone as a substituent: oxo group

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Aldehyde

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Functional group containing a carbonyl (C=O) bonded to a H on one side and a carbon chain on the other side

-Carbonyl carbon is always at position 1 so don't include the aldehyde's location in the name

Suffix: "-al"

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Carboxylic Acid

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Functional group containing a carboxyl, i.e. a carbonyl bonded to an "OH" on one side and a carbon chain on the other side

-Carboxyl carbon is always at position 1 so don't include the carboxylic acid's location in the name

Suffix: "-oic acid"

*If the main carbon chain is a ring structure, the carboxyl carbon is not part of the ring

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Ester

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Functional group in which oxygen is bonded to a carbonyl group on one side and a carbon chain on the other

-Carboxylic acid derivative

Carbonyl carbon is always at position 1 so don't include the ester's location in the name

Prefix: Name of carbon chain on other side of ester

Suffix: "-oate"

Example: "ethyl butanoate"

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Amide

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Functional group containing a N bonded to a carbonyl group

-Carboxylic acid derivative

-Carbonyl carbon is always at position 1 so don't include the amide's location in the name

-Suffix: -"amide"

-Substituents of the N are located at position "N"

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Nitrile

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Functional group containing a C triple-bonded to N

-Triple-bonded C is always at position 1 so don't include the nitrile's location in the name

-Suffix: "-nitrile"

-Nitrile substituent is called cyano group

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Priority for Functional Groups

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1. Carboxylic acid and its derivatives, i.e. amides, esters, and nitriles

2. Aldehydes

3. Ketones

4. Alcohols

5. Amines

6. Alkenes and alkynes

*Functional groups are named as part of the main chain (not as substituents), but the main chain should be numbered so that the carbon to which the functional group is attached receives the lowest number

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Benzene with a simple substituent attached

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ethylbenzene, propylbenzene, butylbenzene, etc.

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Benzene with an aldehyde attached

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Benzaldehyde

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Benzene with a carboxylic acid attached

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Benzoic acid

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Common name for benzene with a methyl group attached

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toluene

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Common name for benzene with a hydroxy group attached

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phenol

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Common name for benzene with an amino group attached

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aniline

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Common name for benzene with an OCH3 (an ether) attached

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anisole

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Common name for benzene with an ethylene attached

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styrene

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Common name for benzene with two methyl groups attached to adjacent carbons

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xylene

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Ortho position

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Substituents attached to adjacent carbons on a ring (two ortho positions available)

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Meta position

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Substituents separated by one carbon on a ring (two meta positions available)

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Para position

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Substituents on opposite sides of a ring (one para position available)