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CnH2n+2

Introduction to Alkanes: Methane, Ethane, and Propane

The Simplest Alkanes


Methane Ethane

(CH4) (C3H8)

CH4 CH3CH3 CH3CH2CH3

(C2H6)

Propane

bp -160C

bp -89C

bp -42C

C4H10

Isomeric Alkanes: The Butanes

n-Butane Isobutane

CH3CH2CH2CH3
(CH3)3CH

bp -0.4C

bp -10.2C

Higher n-Alkanes

CH3CH2CH2CH2CH3 n-Pentane

CH3CH2CH2CH2CH2CH3 n-Hexane

CH3CH2CH2CH2CH2CH2CH3 n-Heptane

The C5H12 Isomers

C5H12

CH3CH2CH2CH2CH3 n-Pentane

(CH3)2CHCH2CH3
Isopentane

(CH3)4C Neopentane

How many isomers?


The number of isomeric alkanes increases as the number of carbons increase. There is no simple way to predict how many isomers there are for a particular molecular formula.

Number of Constitutionally Isomeric Alkanes


CH4 C2H6

C3H8
C4H10 C5H12 C6H14 C7H16

1 1 1 2 3 5 9

C8H18 C9H20 C10H22 C15H32

C20H42
C40H82

18 35 75 4,347 366,319 62,491,178,805,831

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 CH3 Butane (C4H10)

CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3 Nonane (C9H20) CH3 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH2 CH3 Decane (C10H22)

CH3 CH2 CH2 CH2 CH3 Pentane (C5H12)

Nomenclature of the Alkanes

Alkanes always have the ending -ane. Side chains (substituents) are named as alkyl groups.

Common alkyl groups (C1 through C4)


CH3 Methyl CH3 CH2 Ethyl CH3 CH2 CH2 Propyl CH3 CH CH3 Isopropyl (1-Methylethyl) CH3 CH2 CH2 CH2 Butyl CH3 CH CH2 CH3 Isobutyl (2-Methylpropyl) CH3 CH3 CH2 CH CH3 sec-Butyl (1-Methylpropyl) CH3 C CH3 tert-Butyl (1,1-Dimethylethyl)

IUPAC nomenclature of alkanes

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.

H3C CH3 H3C CH2 C CH3 CH CH2 CH2 CH3

CH CH2

CH3

=>

Number the Carbons


Start at the end closest to the first attached group. If two substituents are equidistant, look for the next closest group.
1

CH3
2

CH3 CH CH3
6 7

H3C CH CH CH2 CH2CH3

CH2

Organic nomenclature

CH3 CH2 CH CH3 CH3

2-methylbutane

Find the longest continuous carbon chain


1 2 3

CH3 CH2 CH CH3 CH2 CH3


4 5 3-methylpentane

You must choose the longest continuous carbon chain


4 3 2 1

CH3 CH2 CH CH2 CH2 CH3 CH2 CH2 CH3


5 6 7 4-ethylheptane

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

Longest chain is 7 . (not 6). This is 3-methylheptane.

3. Two or more identical groups are indicated by di, tri, tetra, etc.
2,3,6-trimethylheptane (not 2,5,6-trimethyl heptane)

2,2,6,6,7-pentamethyloctane (not 2,3,3,7,7-pentamethyloctane)

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

Number from the end nearest the first substituent

CH2 CH3 CH3 CH2 CH2 CH CH CH2 CH3


7 6 5 4 3 2 1

CH3
4-ethyl-3-methylheptane

Number from the end nearest the first substituent

CH3 CH3 CH2 CH2 CH CH2 CH CH2 CH3


8 7 6 5 4 3 2 1

CH2 CH3
3-ethyl-5-methyloctane

Use di- with two substituents

CH3 CH3 CH CH CH3


1 2 3 4

CH3
2,3-dimethylbutane

Every substituent must get a number

CH3 CH3 CH2 C


1 2 3

CH2 CH2 CH3


4 5 6

CH3
3,3-dimethylhexane

Number from the end nearest first substituent


CH3 CH3 CH2 CH CH CH2 CH2 CH2 CH2 CH CH3
10 9 8 7 6 5 4 3 2 1

CH3

CH3

2,7,8-trimethyldecane

Number from the end which has the first difference


CH3 CH3 CH2 CH CH CH2 CH2 CH2 CH CH2 CH3
1 2 3 4 5 6 7 8 9 10

CH3

CH3

3,4,8-trimethyldecane

A More-Highly-Substituted Carbon Takes Precedence

CH3
5 4 3

CH3
2

CH3 CH CH2 C CH3

CH3
1

2,2,4-Trimethylpentane

Which end do we number from?

CH3 CH2 CH CH2 CH2 CH CH2 CH3


8 7 6 5 4 3 2 1

CH3

CH2 CH3

3-ethyl-6-methyloctane

IUPAC rules
Name the following compounds.

6-ethyl-2,2,5,7-tetramethylnonane (not 6,7-diethyl-2,2,5-trimethyloctane.

7-tert-butyl-8-isobutyl-4-isopropyldodecane (hyphenated words arent alphabetized).

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

Halogens and other side groups

Flouro F Chloro Cl Bromo Br Iodo I Nitro NO2

N
O

CH 3 CH 2 Br

Bromoethane

Ethyl bromide

CH3 CH3 C CH3 Cl

2-Chloro-2-methylpropane tert-Butyl chloride

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

The isopropyl group can be named as a complex substituent

CH3 CH3 CH
2 1

1-methylethyl

If you can name this, you can name almost anything!


CH3
1 2 3 4 5

CH3
6

CH3 CH CH2 CH CH2 C CH3 CH CH3


7

CH3

CH2 CH2 CH3


9

4-isopropyl-2,6,6-trimethylnonane

Now, rename the isopropyl group. Notice the alphabetical order!


CH3
1 2 3 4 5

CH3
6

CH3 CH CH2 CH CH2 C CH3 CH CH3


7

CH3

CH2 CH2 CH3


9

2,6,6-trimethyl-4-(1-methylethyl)nonane

Naming complex substituents -this one is alphabetized under d


CH3
4 3 2

CH3
1

CH3 CH CH2 CH

1,3-dimethylbutyl

deciding on alphabetical order for complex groups

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

Naming complex substituents


CH3 CH2 CH3 CH3 C
1

CH CH2 CH3
2 3 4

2-ethyl-1,1-dimethylbutyl

This Should Be Fun


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

CH2 CH3
2 3

CH2 CH2 CH2 CH3


6 7 8 9

CH2 CH2 CH3

5-(1-Ethyl-1-methylpropyl)-5-propylnonane

name this two ways -- (the complex group)


CH3 CH3 C CH3 CH2 CH CH2 CH2 CH2 C CH3 CH2 CH2 CH3

CH3

CH2

CH3

7-(1,1-dimethylethyl)-3-ethyl-7-methyldecane 7-tert-butyl-3-ethyl-7-methyldecane

Common Nomenclature Pitfalls

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 CH2 CH CH2 C


2 3
3

CH3 CH CH3
1

CH2 CH2 CH3


2 1

Block diagram for nomenclature

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

CH2 CH2 Cyclopentane

H C

H C C

H CH2 H H CH2

CH2 CH2 CH2 CH2 Cyclohexane

Nomenclature for Cyclic Alkanes

For compounds with a single ring, add the prefix cyclo- to the root name for the alkane comprising the ring.

Nomenclature of the Substituted Cycloalkanes

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

CH3 CH3 CH3 CH2

4-Ethyl-1,1-dimethylcyclohexane

Two ways of naming this


CH3 CH3

CH

CH3

1-isopropyl-2-methylcyclohexane 1-methyl-2-(1-methylethyl)cyclohexane

Numbering Starts at the Most Highly-Substituted Carbon


Cl
2 3 4 6

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