Naming Hydrocarbons

(nomenclature)

Handout: Hydrocarbons: IUPAC names

 Formulas for Hydrocarbons
• Alkanes= CnH2n+2

• Alkenes= CnH2n

• Alkynes= CnH2n-2
Mnemonic for first four prefixes

First four prefixes

• Meth- Monkeys
• Eth- Eat
• Prop- Peeled
• But- Bananas
 Other prefixes

• Pent-

?
Decade
• Oct-
Decimal • Dec-
Decathalon • Hex-, Hept-, Non-
 Hydrocarbons
Alkanes C C Alkenes C C
H H H H H H H H
H C C C C C H H C C C C C H
H H H H H H H H H H

Alkynes C C Aromatics H
H C H
H H H C C
H C C C C C H C C
H C H
H H H
H
 Numbering carbons
Q- Draw pentene H H 1-pentene
A- Where’s the bond? H3C C C C C H
5
1 4
2 3 2
4 1
5
We number C atoms
H H H H
• Always give double/triple bond the lowest
number
• Q – Name:
H
H3C 2-butene
C
C CH3
H
 Naming side chains
• Names are made up
of: side chains, root
• 2,3-dimethyl pentane
• Root is the longest possible HC chain
• Common side chains include:
CH3- methyl CH3CH2- ethyl

CH3CH2CH2- propyl
Br- (bromo), Cl- (chloro),
F(fluoro), I- (iodo)
 Naming side chains
Example: use the IUPAC rules

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 1: choose the correct ending

ene
 Naming side chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 2: longest carbon chain

ene
 Naming side chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

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

1-hexene
ene
 Naming side chains

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

CH3

Rule 4: Assign numbers to each carbon

1-hexene
 Naming side chains

CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3

Rule 4: Assign numbers to each carbon

1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 5: Determine name for side chains
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 6: attach name of branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 7: list alphabetically
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 8,9: group similar branches
2-ethyl-4-methyl-4-methyl-1-hexene
1-hexene
 Naming side chains

CH2 CH2 CH3

ethyl 1 5 6
CH3 CH2 C CH2 C CH3
2 3 4 methyl
CH3
methyl
Rule 8,9: group similar branches
2-ethyl-4,4-dimethyl-1-hexene
 Naming: common vs. IUPAC
• Common names used in the 1800’s are still
used for some compounds today:
O O
H C C H
C Acetylene C
H OH H3C CH3
Formic acid 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 pent-
6 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
 Multiple multiple bonds
H3C CH3 2,3-heptadiene

H3C C C C C C C CH2
2,4,6-nonatriyne 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 2-butyne HC C CH2
H C C C C H H2C CH
H H 1,2,4-pentatriene
CH3CH2CH2CH=C=CH2 1,2-hexadiene
 H H
Cyclic structures H C H
• Cyclic structures are circular H C C H

• Have “cyclo” in name C C

H H
• Benzene is not a cyclic structure H H
• 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 H
H2C CH2 C CH2
H H
C C
HC CH H2C CH2
C C
H H
 Drawing structures: it’s all good
H
2-butene C CH3
H H H3C C
H C C C C H H
CH CH3
H H H H H3C CH
H3C CH CH CH3 CH3
H3C
This is called the
“condensed structure” On a test, choose a
CH3CH=CHCH3 method that shows all Hs
Using brackets can also shorten some formulas:
CH3(CH2)4CH3 vs. CH3CH2CH2CH2CH2CH3
 Naming side chains

H3C CH2 H3C CH2 CH2 CH3

CH CH3 CH CH CH2 CH3
H2C CH2 H3C CH
CH3
CH3
3-methylhexane
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
CH CH2
H3C CH CH3 3-ethyl-2-methylpentane
H2C
CH3

H3C CH3
3-ethyl-1,5,5-
trimethylcyclohexene
CH3
H3C
 More practice

Br
Br Br
4-bromo-7-methyl-2-nonene
Cl
2,5-dibromo-6-chloro-1,3-cycloheptadiene
CH3
H3C C CH2 C CH CH CH CH3
CH3 F 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
 Aromatic nomenclature H3C

There are 2 naming methods

H3C
1) Numbering carbons
2) ortho, meta, para (stomp) 1,2-dimethylbenzene
orthodimethylbenzene
CH3

ST Ortho Meta
H3C

1,3-dimethylbenzene
H3C Para metadimethylbenzene
H3C CH3
Benzene is very stable (does
not generally undergo 1,4-dimethylbenzene
addition) paradimethylbenzene