Naming Hydrocarbons

(nomenclature)

Handout: Hydrocarbons: IUPAC names

Drawing structures: its all good

H
C

2-butene
H
H

H3C
H

H3C CH CH CH3

C
H

CH
H3C
H3C

CH

CH3

CH3
CH3

This is called the

condensed structure On a test, choose a method
that shows all Hs

CH3CH=CHCH3
Using brackets can also shorten some formulas:
CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3

Background: formulas for HCs

Alkanes= CnH2n+2, enes= CnH2n, ynes= CnH2n-2

Remember enes, then think of what would
happen if bond was single or triple instead.
Provides some useful information (e.g. for
compositional analysis, or to check work)
Cannot always tell hydrocarbon type based on
numbers (e.g. propyne vs. propadiene)
Q - how many hydrogens in each of these:
6 carbon alkane
14
Alkene: C22H
44
H3C
CH3
8 (2x5 - 2 = 10 - 2)

Naming: common vs. IUPAC

Common names used in the 1800s are still
used for some compounds today:
O

H
C
H
OH
Formic acid

C
C
Acetylene

C
H3C
CH3
Acetone

The International Union of Pure and Applied

Chemistry (IUPAC) was established in 1900s
Frequent revisions to nomenclature
Systematic method allows an infinite number of
compounds to be named given a few rules

Basic names of hydrocarbons

Hydrocarbon names are based on: 1) class 2)

# of C, 3) side chain type and 4) position
1) name will end in -ane, -ene, or -yne
2) the number of carbons is given by a Prefix
1 meth- 2 eth- 3 prop- 4 but- 5 pent6 hex- 7 hept- 8 oct- 9 non- 10 dec Actually, all end in a, but a is dropped when
next to a vowel. E.g. a 6 C alkene is hexene
Q - What names would be given to these:
7C, 9C alkane heptane, nonane
2C, 4C alkyne ethyne, butyne
1C, 3C alkene does not exist, propene

Mnemonic for first four prefixes

First four prefixes

MethEthPropBut-

Monkeys
Eat
Peeled
Bananas

Other prefixes

Decade
Decimal
Decathalon

Pent Oct Dec Hex-, Hept-, Non-

Numbering carbons
Q- draw pentene
A- Wheres the bond?
We number C atoms

H3C
5
1

1-pentene

4
2

2
4

1
5

Thus, naming compounds with multiple bonds is more

complex than previously indicated
Only if 2+ possibilities exist, are #s needed
Always give double bond the lowest number
Q - Name these

2-butene
H3C

H3C

C
H

H
C

C2H4
CH3
Ethene
CH3 3-nonyne

Multiple multiple bonds

H3C

CH3 2,3-heptadiene

H3C

2,4,6-nonatriyne

CH2
CH3

Give 1st bond (1st point of difference) lowest #

include di, tri, tetra, penta, etc. before ene/yne
Comma between #s, hyphen between #-letter
You do not need to know ene + yne

H
H

H
C

HC

2-butyne
H

H2C

CH2

CH

1,2,4-pentatriene
CH3CH2CH2CH=C=CH2 1,2-hexadiene
H

Cyclic structures

H
H

H
H

C
C

H
Cyclic structures are circular
C C
Have cyclo in name
H
H
H
H
Benzene is not a cyclic structure
cyclopentane
Q- Draw these (note: carbons in a double bond
should be consecutive- 1 and 2, 5 and 6, etc.):
cyclobutene 1,3-cyclopentadiene cyclopropane
H

H2C

CH2

HC

CH

H
C

C
C
H

C
C
H

CH2

H2C

CH2

Naming side chains

CH3

H3C
CH3
Names are made up
of: side chains, root
2,3-dimethylpentane
CH3
Root is the longest possible HC chain
Must contain multiple bonds if present
Add -yl to get name of side chain
H3C
CH3
Common side chains include:
CH
CH3- methyl
CH3CH2- ethyl
*
CH3CH2CH2- propyl (CH3)2CH- isopropyl
iso (branched) is not an IUPAC convention
Br- (bromo), Cl- (chloro), F- (fluoro), I- (iodo)

Naming side chains

Example: use the rules on the bottom of
handout to name the following structure
CH2
CH3 CH2 C

CH2 CH3
CH2 C

CH3

CH3

Rule 1: choose the correct ending

ene

Naming side chains

CH2
CH3 CH2 C

CH2 CH3
CH2 C

CH3

CH3

Rule 2: longest carbon chain

ene

Naming side chains

CH2
CH3 CH2 C

CH2 CH3
CH2 C

CH3

CH3

Rule 3: attach prefix (according to # of C)

1-hexene
ene

Naming side chains

CH2
CH3 CH2 C

CH2 CH3
CH2 C

CH3

CH3

Rule 4: Assign numbers to each carbon

1-hexene

Naming side chains

CH2

CH2 CH3

CH3 CH2 C

CH2 C
3

CH3

CH3

Rule 4: Assign numbers to each carbon

1-hexene

Naming side chains

CH2

ethyl

CH2 CH3

CH3 CH2 C

CH2 C
3

CH3

CH3

methyl

methyl

Rule 5: Determine name for side chains

1-hexene

Naming side chains

CH2

ethyl

CH2 CH3

CH3 CH2 C

CH2 C
3

CH3

CH3

methyl

methyl

Rule 6: attach name of branches

2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene

Naming side chains

CH2

ethyl

CH2 CH3

CH3 CH2 C

CH2 C
3

CH3

CH3

methyl

methyl

Rule 7: list alphabetically

2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene

Naming side chains

CH2

ethyl

CH2 CH3

CH3 CH2 C

CH2 C
3

CH3

CH3

methyl

methyl

Rule 8,9: group similar branches

2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene

Naming side chains

CH2

ethyl

CH2 CH3

CH3 CH2 C

CH2 C
3

CH3

CH3

methyl

methyl

Rule 8,9: group similar branches

2-ethyl-4,4-dimethyl-1-hexene

Naming side chains

Try PE 1 on pg. 1019 (answer to a is wrong)
H3C

H3C

CH2
CH CH3

H2C

CH2

CH CH CH2 CH3
H3C

CH3

3-methylhexane

CH2 CH2 CH3

CH
CH3

4-ethyl-2,3-dimethylheptane

CH3

CH3

CH3

CH3 CH2 CH CH CH CH2 CH CH3

CH2 CH3

5-ethyl-2,4,6-trimethyloctane

Naming side chains

Name the structures below
CH3
H3C

CH

CH2
CH
CH3

H2C

H3C

H3C

3-ethyl-2-methylpentane

CH3

CH3

3-ethyl-1,5,5trimethylcyclohexene
CH3

More practice
Br

4-bromo-7-methyl-2-nonene

Br

2,5-dibromo-6-chloro-1,3-cycloheptadiene

Br
Cl

CH3
H3C

C
CH3

CH2 C
F

CH CH CH CH3

5-fluoro-7,7-dimethyl-2,4-octadiene

Pg. 1049 # 24.5, 24.6, 24.7, 24.14, 24.15

Ignore 24.15 e)

Pg. 1049
24.5 - Recall, the exceptions to organic
compounds are oxides of carbon, carbonates,
bicarbonates, cyanides.
b) is an oxide, d) bicarbonate, e) carbonate
24.6 - This is a straight chain molecule as all
carbons are consecutive.
24.7 - none are possible: a) one too few Hs
(should be CH3CH2CH3), b) one H too many
(should be CH2=CHCH2CH3), c) one H too
many (should be CH3CH=CHCH2CH3).

24.15
2,2-dimethyloctane

1,3-dimethylcyclopentane
1,1-diethylcyclohexane

6-ethyl-5-isopropyl-7-methyl-1-octene

H3C

Aromatic nomenclature
There are 2 naming methods
1) Numbering carbons
2) ortho, meta, para (stomp)

H3C

1,2-dimethylbenzene
orthodimethylbenzene
CH3

ST Ortho
H3C

Meta
Para

Benzene is very stable

(does not generally
undergo addition)

H3C

1,3-dimethylbenzene
metadimethylbenzene
H3C

CH3

1,4-dimethylbenzene
paradimethylbenzene

More practice
Build a molecule that can be named
according to the rules that we have talked
about. Make it challenging.
Place your model at a vacant lab station.
On a scrap piece of paper write the following:
1) your station number, 2) the structure of
your molecule, 3) the name of the structure.
Give this to your teacher.
Rotate through the stations, drawing the
structures and determining their names. At
the end of the class students will reveal the
answer with an explanation.

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