Hydrocarbon Nomenclature

Naming Hydrocarbons
(nomenclature)
Drawing Structures: It’s All Good
H
2-butene C CH3
H H H3C C
H
H C C C C H CH CH3
H H H H H3C CH
CH3
H3C CH CH 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:
CH3CH2CH2CH2CH2CH3 vs. CH3(CH2)4CH3
Basic Naming of Hydrocarbons
Hydrocarbon names are based on: 1) type,
2) # of carbons, 3) side chain type and 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 methene, propene
Mnemonic for First Four Prefixes
First four prefixes

• Meth- Monkeys
• Eth- Eat
• Prop- Peeled
• But- Bananas
Other Prefixes
• Pent-
Decade
?
Decimal
• Oct-
• Dec-
Decathalon • Hex-, Hept-, Non-
Numbering Carbons
Q- draw pentene H H 1-pentene
A- Where’s the double H3C C C C C H
5
1 4
2 3 2
4 1
5
bond? We # C atoms.
H H H H
• Naming compounds with multiple bonds is
more complex than previously indicated.
• When 2+ possibilities exist, #s are needed.
• Always give double bond the lowest number.
• Q - Name these H
H 3C C C2H4
2-butene C CH3
H
ethene
H3C CH3 3-nonyne
Naming Side Chains CH3
• The names of molecules H C CH3
3
with branches are based
on: side chains, root
2,3-dimethylpentane CH3
• The “root” or “parent chain” is usually the

longest possible hydrocarbon chain.
• The root must include multiple bonds if they are
present. If a cyclic structure is present it will be
the root even if it is not the longest chain.
• Side chains are also called “side branches” or
“alkyl groups”. Their names end in -yl.
Common side chains :
-CH3 methyl, -CH2CH3 ethyl, -CH2CH2CH3 propyl
IUPAC Rules for Naming Hydrocarbons
1. Choose the correct ending: -ane, -ene, or -yne
2. Determine the longest carbon chain. Where a
double or triple bond is present, choose the
longest chain that includes this bond. If there is a
cyclic structure present, the longest chain starts
and stops within the cyclic structure.
3. Assign numbers to each C of the parent chain.
For alkenes and alkynes the first carbon of the
multiple bond should have the smallest number.
For alkanes the first branch (or first point of
difference) should have the lowest #. Carbons in a
multiple bond must be numbered consecutively.
4. Attach a prefix that corresponds to the number of
carbons in the parent chain. Add cyclo- to the
prefix if it is a cyclic structure.
IUPAC Rules for Naming Hydrocarbons
5. Determine the correct name for each branch
(“alkyl” groups include methyl, ethyl, propyl, etc.)
6. Attach the name of the branches alphabetically,
along with their carbon position, to the front of the
parent chain name. Separate numbers from
letters with hyphens (e.g. 4-ethyl-2-methyldecane)
7. When two or more branches are identical, use
prefixes (di-, tri-, etc.) (e.g. 2,4-dimethylhexane).
Numbers are separated with commas. Prefixes
are ignored when determining alphabetical order.
(e.g. 2,3,5-trimethyl-4-propylheptane)
8. When identical groups are on the same carbon,
repeat the number of this carbon in the name.
(e.g. 2,2-dimethylhexane)
Naming Side Chains
Example: use the rules on this handout
to name the following structure
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: determine the longest carbon chain

ene
Naming Side Chains
CH2 CH2 CH3
CH3 CH2 C CH2 C CH3
CH3
Rule 3: Assign numbers to each carbon

ene
Naming Side Chains
CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
Rule 3: Assign numbers to each carbon

ene
Naming Side Chains
CH2 CH2 CH3

1 5 6
CH3 CH2 C CH2 C CH3
2 3 4
CH3
Rule 4: attach prefix (according to # of Cs)

1-hexene
ene
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 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 7,8: 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 7,8: group similar branches
2-ethyl-4,4-dimethyl-1-hexene
Page 547-8 Questions 3, 5
CH3 CH CH2 CH3 CH3
propene CH3 CH CH C CH3
CH3 CH CH CH3
2,4-dimethyl-2-pentene
2-butene
CH C CH2 CH3
1-butyne
CH3 CH3
CH2 CH C CH2 CH3 CH3 C CH CH2
CH3 CH2 CH3

a) 3,3-dimethyl-1-pentene b) same
CH3 CH3
CH3 C C CH CH CH2
CH2 CH3
c) 5-ethyl-4-methyl-2-heptyne For more lessons, visit
www.chalkbored.com

Hydrocarbon Nomenclature

Uploaded by

Copyright:

Available Formats

Hydrocarbon Nomenclature

Uploaded by

Document Information

Original Title

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Hydrocarbon Nomenclature

Uploaded by

Copyright:

Available Formats

Naming Hydrocarbons

First four prefixes

• The “root” or “parent chain” is usually the

CH3 CH2 C CH2 C CH3

Rule 1: choose the correct ending

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

Rule 2: determine the longest carbon chain

CH2 CH2 CH3

CH3 CH2 C CH2 C CH3

Rule 3: Assign numbers to each carbon

CH2 CH2 CH3

Rule 3: Assign numbers to each carbon

CH2 CH2 CH3

Rule 4: attach prefix (according to # of Cs)

CH2 CH2 CH3

CH2 CH2 CH3

CH2 CH2 CH3

CH2 CH2 CH3

CH2 CH C CH2 CH3 CH3 C CH CH2

CH3 CH2 CH3

You might also like