HYDROCARBONS

Chapter 13

Learning Outcome
Explain terms saturated and unsaturated HC Describe alkanes Drawing alkanes and its nomenclature -straight, branched chain, cyclic

 HYDROCARBON
Hydrocarbon are compounds which contain only carbon and hydrogen atoms.

HYDROCARBONS

ALIPHATIC (chain structure)

AROMATIC (contain one or more benzene ring)

ALKANES (saturated) contain only single bond

ALKENES (unsaturated) contain C=C

ALKYNES (unsaturated) contain CC

CYCLO-ALKANES (saturated) Alkanes which C atoms are join in rings

CYCLO-ALKENES (unsaturated)

 Saturated hydrocarbons
- compound with C-C - Example : alkanes and cycloalkanes Contain the maximum number of hydrogen atoms that the carbon compound can possess.

 Unsaturated hydrocarbons
-compounds with multiple bonds -Example : alkenes, cycloalkenes, alkynes and aromatic hydrocarbons

They posses fewer than the maximum number of hydrogen atoms.

ALKANES
Alkanes are known as saturated hydrocarbon which contain only single covalent bonds. General formula for straight chain of alkanes is CnH2n+2 where n 1 General formula for cycloalkanes is CnH2n where n 3

Each carbon atom in alkanes is

by sp3 hybridised tetrahedral with four sigma bond (formed the four sp3 hybrid orbitals.) all bond angles are close to 109.5o

Alkanes IUPAC names have the ane suffix.

The First Ten Unbranched Alkanes

Molecular formula CH4 C2H6 C3H8 C4H10 C5H12 C6H14 C7H16 C8H18 C9H20 C10H22 Structural formula CH4 CH3CH3 CH3CH2CH3 CH3(CH2)2CH3 CH3(CH2)3CH3 CH3(CH2)4CH3 CH3(CH2)5CH3 CH3(CH2)6CH3 CH3(CH2)7CH3 CH3(CH2)8CH3 No .of C atoms 1 2 3 4 5 6 7 8 9 10 Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane

H C H H H
H

H C H

H C H H

H H C H

H C H

H C H H

H H C H

H C H

H C H

H C H H
H

H C H

H C H

H C H

H C H

H C H H

 Starting from C4H10 onwards, the alkanes show the phenomenon of chain isomerism. They can exist as linear OR branched alkanes.

Example
C4H10
2-

isobutane

CH3(CH2)2CH3

CH3CH(CH3)2

C5H12

IUPAC NOMENCLATURE
IUPAC International Union of Pure and Applied Chemistry Branched - chain alkanes are named according to the following rules:

Choose the longest continuous chain of carbon atoms; this chain determines the parent name for alkanes. Examples: CH3CH2CH2CH2CH2CH3

Parent name: hexane

CH2CH2CH2CH2CH3 CH2 CH3

Parent name : heptane

Number the longest chain beginning with the end of the chain nearer the substituent. Example:
6 5
4

CH3CH2CH2CH2CHCH3

CH3

substituent

CH CH3CH2CH2CH2CH 3 | 2 CH2 | 1 CH3

substituent

Use rule number 2 to locate the position of the substituent. The position (that is number) and the name of the substituent must be written in front of the parent chain.

Examples:
6 5
4

CH3CH2CH2CH2CHCH3 CH3 2-methylhexane

Substituent -methyl at C2

Substituent -methyl at C7 6 5 4 3 3 CH3CH2CH2CH2CHCH3

| 2 CH 2 | 1 CH 3

3-methylheptane

Some Common Substituent Groups

Alkane Name methyl ethyl propyl isoprop yl butane Substituent

methane
ethane propane

CH3

CH2CH3 CH2CH2CH3
CHCH3 CH3

butyl

CH2CH2CH2CH3

isobutyl

CH2CHCH3

CH3 sec-butyl
CHCH2CH3 CH3 CH3 CCH3

tert-butyl

neopentyl

CH3 CH3 CH2CCH3 CH3

cyclopropyl cyclobutyl

phenyl

C6H5 or

benzyl
CH2

Name Bromo Chloro

Substituent -Br -Cl

Flouro
Iodo Hydroxyl Amino Cyano Nitro

-F
-I -OH -NH2 -CN -NO2

If two or more substituents are present, give each substituent a number corresponding to its location on the longest chain. the substituent should be listed alphabetically. In alphabetizing, the prefixes di, tri, tetra, sec-, tert- are ignored except iso and neo.

Example:
1 2 3 4 5 6

CH3CHCH2CHCH2CH3 | | CH3 CH2 | CH3 4-ethyl-2-methylhexane

If two substituents are present on the same carbon atom, use that number Example: twice CH3 |3 4 5 6 CH3CH2CCH2CH2CH3 | 2CH 2 | 1CH 3 3-ethyl-3-methylhexane

~If two or more identical substituents are present, use prefixes di-(2 identical substituents), tri-(3 identical substituents), tetra-(4 identical substituents). ~ Commas are used to separate numbers from each other. Example: CH3CHCH CH3 | | CH3 CH3

2,3-dimethylbutane

If there are two chains of equal length as the parent chain, choose the chain with the greater number of substituents.

4
4

3
3

1 2

CH3CH2-CH CH CH CHCH3 | | | | 5 CH3 CH2 CH3 CH3 | CH62 | 7 CH3 2,3,5-trimethyl-4propylheptane (four substituents) 4-sec-butyl-2,3-dimethylheptane

(three substituents)

If branching occurs at an equal distance from either end of the longest chain, choose the name that gives the lower number at the first point of difference.
6 5 4 3 2 1

CH3CHCH2CH CHCH3 1 2 3 4 5 6 | | | CH3 CH3 CH3

2,3,5-trimethylhexane (NOT 2,4,5-trimethylhexane)

CYCLOALKANES
Cycloalkanes alkanes which carbon atoms are joined in rings. Cycloalkanes are known as saturated hydrocarbon, because it has the maximum number of bonded hydrogen ( only has single bonds). General formula: CnH2n where n = 3, 4, 5,

NOMENCLATURE OF CYCLOALKANES

Cycloalkanes with only one ring are named with the prefix cyclo- to the names of the alkanes (contain the same number of carbon atoms)

Monocyclic compounds
C 3H 6 C 4H 8 C5H10 cyclopropane cyclobutane cyclopentane

If only one substituent is present, it is not necessary to designate its position. Examples:

Chlorocyclopropane
Cl

CH3

Methylcyclohexane

If two substituents are present, number carbon in the ring beginning with the substituent according to the alphabetical order

and
number in the direction that gives the next substituent the lowest number possible.

Examples: CH3
3 4 5 6 2 1

CH2CH3

1-ethyl-2-methylcyclohexane NOT 1-ethyl-6-methylcyclohexane

Cl

Cl

1,3-dichlorocyclopentane (NOT 1,5-dichlorocyclopentane)

When three or more substituents are present, begin at the carbon with substituent that leads to the lowest set of locants.

Example:
2 1

Locants
3 2

CH2CH3
4
1

chloro ethyl methyl

3

3
4 6 5

2
4 1

Cl

CH3

6 5

1-chloro-3-ethyl-4-methylcyclohexane 4- chloro-2-ethyl-1-methylcyclohexane

H 3C

CH2CH3

CH3 1-ethyl-1,3-dimethylcyclopentane (NOT 3-ethyl-1,3-dimethylcyclopentane)

When a single ring system is attached to a single chain with a greater number of carbon atoms

or
when more than one ring system is attached to a single chain, then it is appropriate to name the compounds as

cycloalkylalkane.
Number of C at ring

Number of C at linear chain

1,3-dicyclohexylpropane
cycloalkyl alkane

Examples:

CH2CH2CH2CH2CH3

1-cyclobutylpentane

Name the following compounds according to IUPAC nomenclature

H3C

CH2CH3 H3C CH CH3

H3C C 2 H5

CH

CH3

CH CH 2 CH CH CH3 C 2 H5

CH3CH2 CHCH 2CH3 CH CH3 H3C

Br H3C CH 2 CH 3

CH3 H3C H3C C CH CH 2 CH 2 CH3 CH3

CH3 CH 3CH 2 CH3 CH3

Draw the structure for each of the following compounds

(a) (b) (c) (d) 1,1-dichloro-3-methylcyclohexane 2,2-dimethyl-3-cyclohexylbutane 1-bromo-5-chloro-3-ethyl-3-methylpentane] 5-sec-butyl-2,4-dimethylnonane