Lievens, January 2012

University of California, Davis Chemistry 118 Series

Basic IUPAC Nomenclature I

Straight Chain Alkanes

• Straight chain alkanes have only carbon and hydrogen atoms.

• Formula is CxH(2x+2)

• All the carbons in alkanes are sp3 hybridized and in straight chain alkanes
all the carbons are linked in a straight line. (Exactly two ends)

• Straight chain alkanes are named for the number of carbons in the chain.

• All straight chain alkane names end in –ane; which shows that the only
functional group present is alkanes.

Basic Straight Chain Alkanes C1 - C10

C1 methane CH4 CH4

C2 ethane CH3CH3

C3 propane CH3CH2CH3

C4 butane CH3(CH2)2CH3

C5 pentane CH3(CH2)3CH3

C6 hexane CH3(CH2)4CH3

C7 heptane CH3(CH2)5CH3

C8 octane CH3(CH2)6CH3

C9 nonane CH3(CH2)7CH3

C10 decane CH3(CH2)8CH3

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Advanced Straight Chain Alkanes C11 – C20

C11 undecane CH3(CH2)9CH3

C12 dodecane CH3(CH2)10CH3

C13 tridecane CH3(CH2)11CH3

C14 tetradecane CH3(CH2)12CH3

C15 pentadecane CH3(CH2)13CH3

C16 hexadecane CH3(CH2)14CH3

C17 heptadecane CH3(CH2)15CH3

C18 octadecane CH3(CH2)16CH3

C19 nonadecane CH3(CH2)17CH3

C20 icosane CH3(CH2)18CH3

Notes:
• With 5 or more carbons straight chain alkanes count generally using
Greek prefixes.
• Memorizing 1-10 is sufficient for 8A, students in 118A should know 1-
20.

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Basic IUPAC Nomenclature II

Alkyl Groups

• You can make an alkane into an alkyl group by removing a hydrogen.

• Alkyl groups of straight chains are named by dropping the ending –ane
and adding the ending –yl to the base name of the chain.

H H H H H H
H C H H C H C C H H C C
H H H H H H
a methane molecule a methyl group an ethane molecule an ethyl group

• Once we get to three or more carbons there are choices. We can form
straight chain or branched alkyl groups.

H H H H H H H H H
H C C C H C C C H H C C C H
H H H H H H H H
a propyl group a propane molecule an isopropyl group
a straight chain or a branched chain
n-alkyl substituent substituent

• Many smaller branched alkyl groups get common names. These names
are old fashioned, but are still often used. The following common names
are in general use and should be remembered.

H H H
isopropyl H C C C H
X
the iso- prefix is included in alphabetization
H H

H H H
isobutyl H C C C X the iso- prefix is included in alphabetization
H C H
H H
H

H H H H
sec-butyl H C C C C H the sec- prefix is italicized and separate
H H H X from the name and is NOT included in
alphabetization.
H
H H
H C
tert-butyl H C C the tert- prefix is italicized and separate
H C X from the name and is NOT included in
H H alphabetization.
H

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

• Branched alkyl groups can also be named by IUPAC by treating each

branch as a substituent off the main chain. When naming branched alkyl
groups using IUPAC the carbon attached to the point of interest (e.g. main
chain) is carbon one.

methyl
Common IUPAC
2
H H H 1

isopropyl H C C C H 1-methylethyl
X
H H
methyl

H H H
isobutyl H C C C X 2-methylpropyl
2
3 1
H C H
H H
H
methyl
H H H H 2

sec-butyl H C C C C H
1 3
1-methylpropyl
H H H X

H
H H methyl
H C
tert-butyl H C C 1,1-dimethylethyl *
H C 2
1 X
H H
H
* Unlike
most prefixes di-, tri-, tetra- etc prefixes in branched substituents count
towards alphabetical order. e.g., 1,1-Dimethylethyl rather than 1,1-diMethylethyl.

Notes:
• Alkyl groups are generally substituents meaning they have a bond
attached to something of note (e.g., halogens, amines, alcohols, ethers,
longer chains).

• Alkyl groups are never complete molecules on their own.

• The variable –R represents any alkyl group.

• iso- groups generally have the form (CH3)2CH-X

• sec- groups attach via a secondary carbon

• tert- groups attach via a tertiary carbon

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Basic IUPAC Nomenclature III

Branched Chain Alkanes/Haloalkanes

• Branched chain alkanes have only carbon and hydrogen atoms.

haloalkanes have a halogen (F, Cl, Br, I)

• Formulas are CnH(2n+2) for alkanes or CnH(2n+2-y)Xy for haloalkanes

• All the carbons in alkanes are sp3 hybridized and in branched chain
alkanes the chain forks. (More than two ends)

•IUPAC Nomenclature of branched alkanes follows these steps:

1) Find the longest chain of continuous carbons. This is now the main
chain. Name this chain as if it were a straight chain alkane.
a. If two chains are the same length choose the one with more
branches.
2) Count the carbons in the main chain left to right and right to left. The
direction you first run into a substituent is the direction use to number
the chain.
a. If the numbers are the same go to the next nearest substituent
b. If the numbers are exactly the same regardless of direction the
lower numbers go to the first substituent in alphabetical order.
3) Give each substituent a number according to which carbon itʼs
attached to.
4) List the substituents in alphabetical order in front of the main chain.
a. Branched substituents get parenthesis around them
b. Numbers are separated from numbers by commas
c. Numbers are separated from words by hyphens
5) Multiple straight chain substituents of the same kind are combined and
given a prefix to indicate the number (di-, tri-, tetra-). These prefixes do
not count towards alphabetical order. If the substituent is branched
(bis-, tris-, tetrakis-) are used.
Notes:
• Sometimes it helps to think of each carbon in the main chain as a house
on a street. The substituents that live there each get an address (number)
according to which house (carbon) they live at.
• Once youʼve found your main chain circling or labeling it can show you
what you still have left to name as substituents
• To find the longest chain pick an end and follow it to the first branch. Make
sure you have the longest end on that branch. Follow the chain to the next
branch selecting the longest continuing chain each time you find a branch
until you run out of molecule.
• F- is Fluoro, Cl- is Chloro, Br- is Bromo, I- is Iodo. They get no special
priority

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Examples:

Cl Br

Br
Compound A Compound B

Cl Br
1)

Br
a nonane an octane

We could have started in the lower left We could start at the lower left
or ended in the upper right and gotten methyl and the result would be
the same length, but this chain has 5 exactly the same.
substituents rather than 3 or 4.

Cl Br
2) 5
3 7 3
4 6
1 2 7 8 6 5 4 2
1
Br
8
9
Left to right we get substituents at Left to right we get substituents at
positions 2,3,5,7,and 8 positions 2, 5, 6, and 7.
Right to left we also get substituents at Right to left we also get substituents at
postions 2,3,5,7, and 8. postions 2,3,4, and 7.
The first substituent L-->R is Chloro, 2 = 2 so we go on to the next
the first substituent R-->L is Methyl. substituent and 3 < 5 so we use R--> L
C comes first so L-->R is correct.

3) Cl Br
3 5 7 3
4 6
1 2 7 8 6 5 4 2
1
Br
8
9
2-bromo
2-chloro 3-bromo
3-ethyl 4-isopropyl or 4-(1-methylethyl)
5-methyl 7-methyl
7-ethyl
8-methyl

4,5)

2-chloro-3,7-diethyl-5,8-methylnonane 2,3-dibromo-4-isopropyl-7-methyloctane
or
2,3-dibromo-7-methyl-4-(1-methylethyl)octane

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Practice Alkane and Haloalkane Nomenclature:

I
Compound A
Compound B Compound C

Cl Br
Cl
Cl

Cl Br
Br
Compound D
Compound E
Compound F
Br
F Cl
Br
Compound G Cl
Compound H Compound I

Cl Br

Cl
Br
Compound J
Compound K Compound L
Cl
Br Br
F
Br Br
Compound M
Compound N
Compound O

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Practice Alkane and Haloalkane Nomenclature Key:

Compound A: 2,2-dimethylhexane

Compound B: 4-isopropyl-3,6-dimethyloctane or
3,6-dimethyl-4-(1-methylethyl)octane

Compound C: 4-ethyl-4-iodo-3,6-dimethyloctane

Compound D: 6,7-dibromo-2,3-dichlorononane

Compound E: 7-bromo-8-chloro-3,3-diethyldecane

Compound F; 5-sec-butyl-3-chloro-6-ethyl-2-methylnonane or
3-chloro-6-ethyl-2-methyl-5-(1-methylpropyl)nonane

Compound G: 2,3-dibromo-2,4,4-trimethylpentane

Compound H: 5-ethyl-1-fluoro-6,6-dimethylheptane

Compound I: 3,4-dichloro-7,8-dimethyldecane

Compound J: 3-ethyl-2,6,7-trimethylnonane

Compound K: 5-sec-butyl-2-chloro-6-isopropyldecane or
2-chloro-6-(1-methylethyl)-5-(1-methylpropyl)decane

Compound L: 6,7-dibromo-1-chloro-4-isobutyloctane or
6,7-dibromo-1-chloro-4-(2-methylpropyl)octane

Compound M: 2-chloro-3-fluorobutane

Compound N: 2,2,3,3-tetrabromo-5,6-diethyloctane

Compound O: 4-ethyl-2,3-dimethylhexane

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Basic IUPAC Nomenclature IV

Cycloalkanes

• Cycloalkanes have only carbon and hydrogen atoms.

• Formulas are CnH(2n)

• All the carbons in alkanes are sp3 hybridized and in a cycloalkane a ring is
formed. (No ends)

• Cycloalkanes can be substituted like regular alkanes

•IUPAC Nomenclature of cycloalkanes follows these steps:

1) Find the ring. This is now the main chain. Count the carbons and name
chain as if it were a straight chain alkane. Add the prefix cyclo- to the
name to get the full base name of the ring.
2) If there are substituents:
a. 1 substituent  the carbon the substituent is attached to is
carbon-1. There is no need to number the substituent.
b. 2 substituents  the substituents will have the same numbers,
so the first in alphabetical order will be at carbon-1. Substituents
should be numbered.
c. 3 or more substituents  Number substituents so that the
lowest possible numbers are used. If there is a tie use
alphabetical order.
3) Give each substituent a number according to which carbon itʼs
attached to.
4) List the substituents in alphabetical order in front of the main chain.
a. Branched substituents get parenthesis around them
b. Numbers are separated from numbers by commas
c. Numbers are separated from words by hyphens
5) Multiple straight chain substituents of the same kind are combined and
given a prefix to indicate the number (di-, tri-, tetra-). These prefixes do
not count towards alphabetical order. If the substituent is branched
(bis-, tris-, tetrakis-) are used.
6) Indicate stereochemistry using cis- or trans- prefixes for disubstituted
rings or R,S labels for multiply substituted rings.
Notes:
• Cycloalkanes can become cycloalkyl substituents

• Two substituents on the same carbon are almost always 1,1-disubstituted.

• Cis-substituents are on the same side and sound similar, trans-

substituents are on opposite sides and you have to go across the ring.

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Examples:

Cl Cl

Compound C Compound D

Cl Cl
1)

a cyclohexane a cyclopentane

Cl Cl
2)
1 1
2 5
2
3 3 4

butyl comes before propyl 1, 1, 3, 4 is lower than 1, 2, 4, 4

and 1,3 is lower than 1, 5 (1,1 always wins)
ethyl comes before methyl so we
go counterclockwise

Cl Cl
3)
1 1
2 5
2
3 3 4

1-sec-butyl or 1-methylpropyl 1-chloro

3-propyl 1-chloro
3-ethyl
4-methyl
4,5)

1-sec-butyl-3-propylcyclohexane 1,1-dichloro-3-ethyl-4-methylcyclopentane
or
1-(1'-methylpropyl)-3-propylcyclohexane

(R) Cl Cl
6)
(R)
(S)
(S) (S)

same side = cis ethyl = #1 CH, #2 CH2CCl2, #3 CH2CH3, #4 H

=S
methyl = #1 CH, #2 CH2CCl2, #3 CH3, #4 H
=S

cis-1-sec-butyl-3-propylcyclohexane (3S,4S)-1,1-dichloro-3-ethyl-4-methylcyclopentane
or
cis-1-(1'-methylpropyl)-3-propylcyclohexane

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Practice Cycloalkane Nomenclature:

CH3
Br

Cl
Cl
Compound A Compound B Compound C

Br
Cl

Cl

Compound D Compound E Compound F

Cl
Cl Cl

F
Compound G Compound H Compound I

Br
Br

Cl
F

Compound J Compound K Compound L

Br
Br

Compound M Compound O
Compound N

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Lievens, January 2012
University of California, Davis Chemistry 118 Series

Practice Cycloalkane Nomenclature Key:

Compound A: 3-bromo-2-chloro-1-ethyl-4-methylcyclohexane

Compound B: trans-1-chloro-2-isopropylcyclobutane or
trans-1-chloro-2-(1-methylethyl)cyclobutane or
(1R,2S)-1-chloro-2-(1-methylethyl)cyclobutane

Compound C: 1-butyl-2-sec-butyl-4-tert-butylcyclooctane or
1-butyl-4-(1,1-dimethylethyl)-2-(1-methylpropyl)cyclooctane

Compound D: 2-bromo-1,1-dichlorocyclopropane

Compound E: 1,3-diethyl-5-isopropylcycloheptane or
1,3-diethyl-5-(1-methylethyl)cycloheptane

Compound F: cis-1-ethyl-3-isobutylcyclopentane or
cis-1-ethyl-3-(2-methypropyl)cyclopentane or
(1R,3R)-1-ethyl-3-(2-methypropyl)cyclopentane

Compound G: trans-1-ethyl-3-isopropylcyclopentane or
trans-1-ethyl-3-(1-methyethyl)cyclopentane or
(1R,3R)-1-ethyl-3-(1-methyethyl)cyclopentane

Compound H: 1-sec-butyl-2-chloro-4-ethyl-3-methylcyclohexane or
3-chloro-1-ethyl-2-methyl-4-(1-methylpropyl)cyclohexane

Compound I: 1,1-dichloro-4-fluoro-5-propylcycloheptane

Compound J: 2-chloro-5-cyclobutyl-4-ethylheptane

Compound K: cis-1-bromo-4-tert-butylcyclohexane or
cis-1-bromo-4-(1,1-dimethylethyl)cyclohexane

Compound L: 3-bromo-2-cyclopentyl-4-ethyl-6-fluoroheptane

Compound M: 1,2-dibromo-3-ethyl-5-isopropylcyclohexane or
1,2-dibromo-3-ethyl-5-(1-methylethyl)cyclohexane

Compound N: trans-1-cyclopropyl-3-propylcyclohexane or
(1R,3R)-1-cyclopropyl-3-propylcyclohexane

Compound O: cis-1-isopropyl-4-propylcyclooctane
cis-1-(1-methylethyl)-4-propylcyclooctane
(1S,4R)-1-(1-methylethyl)-4-propylcyclooctane

12