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(CH4) (C3H8)
(C2H6)
Propane
bp -160C
bp -89C
bp -42C
C4H10
n-Butane Isobutane
CH3CH2CH2CH3
(CH3)3CH
bp -0.4C
bp -10.2C
Higher n-Alkanes
CH3CH2CH2CH2CH3 n-Pentane
CH3CH2CH2CH2CH2CH3 n-Hexane
CH3CH2CH2CH2CH2CH2CH3 n-Heptane
C5H12
CH3CH2CH2CH2CH3 n-Pentane
(CH3)2CHCH2CH3
Isopentane
(CH3)4C Neopentane
C3H8
C4H10 C5H12 C6H14 C7H16
1 1 1 2 3 5 9
C20H42
C40H82
Systematic Nomenclature
International Union of Pure and Applied Chemistry IUPAC Committee on Organic Nomenclature
The alkanes
CH4 Methane CH3 CH3 Ethane CH3 CH2 CH3 Propane (C3H8) (C2H6) (CH4) CH3 CH2 CH2 CH2 CH2 CH3 Hexane (C6H14) CH3 CH2 CH2 CH2 CH2 CH2 CH3 Heptane (C7H16)
CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH3 Octane (C8H18)
CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3 Nonane (C9H20) CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3 Decane (C10H22)
Alkanes always have the ending -ane. Side chains (substituents) are named as alkyl groups.
identify the longest chain -- parent number from the end closest to first branch Name the groups attached to the chain, using the carbon number as the locator. Alphabetize substituents. Use di-, tri-, etc., for multiples of same substituent combine number and name of substituent with parent name, separating with hyphen
Longest Chain
The number of carbons in the longest chain determines the base name: ethane, hexane. If there are two possible chains with the same number of carbons, use the chain with the most substituents.
CH CH2
CH3
=>
CH3
2
CH3 CH CH3
6 7
CH2
Organic nomenclature
2-methylbutane
IUPAC rules
1. Find the longest straight chain = parent chain 2. Number the parent chain in the direction that gives the lowest number to the substituents at the first point of difference.
CH2 CH3 CH2 CH2 CH2 CH3
CH CH3
3. Two or more identical groups are indicated by di, tri, tetra, etc.
2,3,6-trimethylheptane (not 2,5,6-trimethyl heptane)
IUPAC rules
4. Different groups are listed in alphabetical order (di, tri, tetra, etc. dont count; n, sec, tert dont count; iso does). 6-ethyl-5-isopropyl-2,2-dimethyloctane
5. If the numbering is the same in both directions, choose the numbering to follow the alphabetical order.
5-ethyl-6-methyldecane
IUPAC rules
6. When two or more chains compete for the longest, the choice goes to the one with the greater number of side groups. 2,4,6-trimethyl-5-propyloctane
CH3
4-ethyl-3-methylheptane
CH2 CH3
3-ethyl-5-methyloctane
CH3
2,3-dimethylbutane
CH3
3,3-dimethylhexane
CH3
CH3
2,7,8-trimethyldecane
CH3
CH3
3,4,8-trimethyldecane
CH3
5 4 3
CH3
2
CH3
1
2,2,4-Trimethylpentane
CH3
CH2 CH3
3-ethyl-6-methyloctane
IUPAC rules
Name the following compounds.
OR 7-(1,1-dimethylethyl)-4-(1-methylethyl)8-(2-methylpropyl)dodecane
Good Luck!
CH3 CH3 C CH3 CH2 CH CH2 CH2 CH2 CH2 C CH3 CH2 CH2 CH2 CH2 CH3 CH2 CH3
CH2
CH3
7-(1,1-Dimethylbutyl)-3-ethyl-7-methyldodecane
Branched Substituents
H3C CH CH3
isopropyl
CH3 H3C CH CH2 H2C CH3 CH CH3 H3C CH3 C CH3
sec-butyl
isobutyl
CH3 H3C C CH2 CH3
tert-butyl (t-butyl)
neo-pentyl
N
O
CH 3 CH 2 Br
Bromoethane
Ethyl bromide
CH 3 CH Br
CH CH 3
CH 2 CH 3
2-Bromo-3-methylpentane
Complex Substituents
If the branch has a branch, number the carbons from the point of attachment. Name the branch off the branch using a locator number. Parentheses are used around the complex branch name.
1
2
=>
3 1-methyl-3-(1,2-dimethylpropyl)cyclohexane
CH3 CH3 CH
2 1
1-methylethyl
CH3
6
CH3
4-isopropyl-2,6,6-trimethylnonane
CH3
6
CH3
2,6,6-trimethyl-4-(1-methylethyl)nonane
CH3
1
CH3 CH CH2 CH
1,3-dimethylbutyl
Complex groups are alphabetized under the first letter of the name
(1,3-dimethylbutyl)
= d (1,1,2-trimethylpropyl) = t (1-ethyl-1,2-dimethylbutyl) = e
CH CH2 CH3
2 3 4
2-ethyl-1,1-dimethylbutyl
CH2 CH3
2 3
5-(1-Ethyl-1-methylpropyl)-5-propylnonane
CH3
CH2
CH3
7-(1,1-dimethylethyl)-3-ethyl-7-methyldecane 7-tert-butyl-3-ethyl-7-methyldecane
Did not find the longest carbon chain Numbered chain from the wrong end Forgot to repeat number for each identical substituent; forgot to use di- tri- tetra-, etc. Used iso, sec, or tert as part of a parent name Confusing propyl / isopropyl, etc. Writing the name as more than one word Incorrect punctuation
degree of substitution
CH3 R primary (1) R CH2 R secondary (2)
R R CH R R
R C R R
tertiary (3)
quaternary (4)
Degree of Substitution
CH3 1
1 3
1
CH3 1 CH3
4
2
CH3 CH CH3
1
LOCANT numbers
PREFIX
N number
STEM
SUFFIX ending
substituents
-ALK(AN)-
cyclic molecules
H C H C H H H H C C H H C C H H H CH2 CH2 CH2 CH2 Cyclobutane H H H C C C H H H H C H H CH2 H CH2 CH2 Cyclopropane H C H H C H C H H C C HH H H CH2 CH2 CH2
H C
H C C
H CH2 H H CH2
For compounds with a single ring, add the prefix cyclo- to the root name for the alkane comprising the ring.
If there is only one substituent, do not use the 1. If there is more than one substituent, you must use all numbers, including 1! Number around the ring in a direction to get from the first substituent to the second substituent by the shorter path. For equivalent degrees of substitution, number in a direction that follows the alphabetical sequence. A carbon with greater substitution has precedence in numbering.
Br
Bromocyclopropane
CH3 CH3
1,1-Dimethylcyclohexane
4-Ethyl-1,1-dimethylcyclohexane
CH
CH3
1-isopropyl-2-methylcyclohexane 1-methyl-2-(1-methylethyl)cyclohexane
CH3 CH3
1
7
CH3
2-Chloro-1,1,6-trimethylcycloheptane
cycloalkyl groups
Cyclopropyl
Cyclobutyl
Cyclopentyl
Cyclohexyl
CH 3 CH 2 C CH 3
CH 2 CH 3
3-Cyclobutyl-3-methylpentane
CH3 CH2 CH
CH3
2-Cyclobutylbutane
sec-Butylcyclobutane
IUPAC rules
Name the following cycloalkanes. Check your answers by clicking on the arrow. 1,1,2-trimethycyclohexane
4-cyclopentyl-2,3-dimethylhexane
1,2-dicyclopropylethane