Naming Hydrocarbons
(nomenclature)
Organic Compounds
• __________ Compounds - any covalently
bonded compound containing carbon
(except __________ , __________ and
__________ )
Hydrocarbons
• __________ - Organic compounds that
contain only carbon & hydrogen
• __________ - contain only single covalent
bonds
• __________ - contain one or more carbon
- carbon double bond
• __________ - contain one or more carboncarbon triple bond
Saturated & Unsaturated
Hydrocarbons
• Saturated hydrocarbons – contain only
__________ carbon-carbon bonds
(__________ )
• Unsaturated hydrocarbons – contain
double carbon-carbon bonds
(__________) or triple carbon-carbon
(__________ ) bonds
Formulas
• Alkanes = CnH2n+2
• Alkenes = CnH2n
• Alkynes = CnH2n-2
Nomenclature
• Must memorize prefixes
• To name, look at the
•
•
•
formula for the
hydrocarbon
Determine if it is an
alkane, alkene, or alkyne
Use the prefix for the
number of carbons
Add ending (ane, ene,
yne)
Prefix
# of carbon
atoms
Meth-
1
Eth-
2
Prop-
3
But-
4
Pent-
5
Hex-
6
Hept-
7
Oct-
8
Non-
9
Dec-
10
Example
• Name C3H8
Mnemonic for first four prefixes
First four prefixes
•
•
•
•
MethEthPropBut-
Monkeys
Eat
Peeled
Bananas
Numbering carbons
Draw 1-pentene
Name these
H3C
H 3C
C
H
H
C
C2H4
CH3
CH3
Multiple multiple bonds
H3C
H3C
CH3
C
C
C
C
C
C
CH2
• Give 1st bond (1st point of difference) lowest #
• include di, tri, tetra, penta, etc. before ene/yne
• Comma between #s, hyphen between #-letter
H
H
C
H
H
C
C
C
CH3
HC
H
H
CH3CH2CH2CH=C=CH2
H2C
CH
C
CH2
Cyclic structures
• Cyclic structures are circular
• Have “cyclo” in name
Draw the following:
cyclobutene 1,3-cyclopentadiene cyclopropane
Name the following:
H
H
H
H
C
C
H
H
C
H
C
C
H
H
H
Naming side chains
Root is the longest possible HC chain
Must contain multiple bonds if present
Add -yl to get name of side chain
Common side chains include:
CH3- methyl
CH3CH2ethyl
CH3CH2CH2- propyl
(CH3)2CHisopropyl
Br- (bromo)
Cl- (chloro)
F- (fluoro)
I- (iodo)
CH3
H3C
CH3
CH3
Naming side chains
Example: name the following structure
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
Step 1 - choose the correct ending
CH3
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
Step 2 - find the longest chain
CH3
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Step 3 - add the prefix naming the longest chain
Naming side chains
CH2
CH3 CH2 C
CH2 CH3
CH2 C
CH3
CH3
Step 4 - number the longest chain with
the lowest number closest to the
double bond
Naming side chains
CH2
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
Step 5 - add that number to the name
6
CH3
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
Step 6 - Name the side chains
6
CH3
methyl
methyl
Naming side chains
CH2
ethyl
CH2 CH3
1
CH3 CH2 C
2
5
CH2 C
3
4
CH3
Step 7 - Place the side chains in
alphabetical order & name the
compound
6
CH3
methyl
methyl
Name
H3C
CH2
H3C
CH CH3
H2C
CH2
CH CH CH2 CH3
H3C
CH3
CH2 CH2 CH3
CH
CH3
CH3
CH3
CH3
CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
Draw the structures below
3-ethyl-2-methylpentane
3-ethyl-1,5,5-trimethylcyclohexene
More practice
Br
CH3
H3C
C
CH3
CH2 C
F
CH CH CH CH3
Functional Groups
Class
Alcohol
Functional group
R – OH
Ether
R — O — R’
Aldehyde
O
||
R—C—H
Ketone
O
||
R — C — R’
Carboxylic acid
O
||
R — C — OH
Ester
Amine
O
||
R — C — O — R’
R’
|
1
CH2
CH3
CH2
CH2
CH2
CH2
CH3
CH2
2 CH3
4
CH
CH3
octane
CH2
CH2
CH2
CH
CH3
CH3
CH2
H2C
CH3
2,5-dimethyloctane
CH
CH3
3
CH3 CH2 CH CH C
2,2-dimethyl-3-hexene
CH3
H2C
CH3
CH2
CH2 CH
CH2 CH3
1,3-diethylcyclopentane
5
CH2
CH
CH3
CH2
CH2
CH
CH2
CH2
CH3
4-nonene
6
CH2
H2C
8
CH2
cyclopropane
7
H3C
H3C
3,3-dimethylcyclopentene
6-ethyl-2-octyne
9
10
3-methylhexane
H3C
H3C
CH CH CH2 CH3
CH2
CH CH3
H2C
H3C
CH2
CH
CH3
4-ethyl-2,3-dimethylheptane
CH3
11
CH2 CH2 CH3
CH3
CH3
CH3
CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
5-ethyl-2,4,6-trimethyloctane
12
13
3,4-diethyl-2-hexene
CH3
CH
CH3
C
CH3
H 2C
CH2
HC
CH
cyclobutene
CH2
15
CH3
CH2 CH
CH2 CH
CH2
CH2 CH3
CH
CH2
14
CH2
CH
H2C
CH2
CH2 CH2
CH2
benzene
CH3
H3C
1,2-dimethyl-6-propylcyclodecane
CH3
16
CH3
H3C
CH3
2,7,8-trimethyldecane
CH3
17
19
CH3 CH CH CH2 CH2 CH3
2-hexene
CH3
CH2
CH3 CH2 C CH2 CH3
18 H C
3
CH3
CH2
CH3
H3C
4-ethyl-1,2-dimethylcycloheptane
3,3-diethylpentane
20
CH3
CH
H3C
CH2
CH
CH3
H2C
CH3
3-ethyl-2-methylpentane
21
H3C
CH3
H3C
3-ethyl-1,5,5-trimethylcyclohexene
CH3