Naming Hydrocarbons:

Alkanes
Organic Compounds
Organic Compounds - any covalently bonded
compound containing carbon
Carbon forms four bonds ----> great diversity of
structures
Hydrocarbons
Hydrocarbons - Organic compounds that contain
only carbon & hydrogen
alkanes - contain only single covalent bonds
alkenes - contain one or more carbon - carbon double bond
alkynes - contain one or more carbon-carbon triple bond
Saturated vs. Unsaturated Hydrocarbons

Saturated hydrocarbons – contain

Carbon is
only single carbon-carbon bonds “saturated” with
alkanes bonds

Unsaturated hydrocarbons – contain

double or triple carbon-carbon bonds
alkenes and alkynes
Representing Organic Compounds
Four ways of representing the same molecule:
a) molecular formula b) structural formula
C3H8

c) condensed structural formula

CH3CH2CH3

d) skeletal formula
each end and corner represents a carbon
each carbon is assumed to form four bonds
carbons are bonded to hydrogens (not shown), unless otherwise indicated
atoms other than carbons and hydrogens are represented by their symbols
Alkanes
Root # of carbon
General formula: CnH(2n+2) prefixes atoms
Meth- 1
Eth- 2
Nomenclature Prop- 3
root prefix based on # of But- 4
carbons Pent- 5
ending: -ane Hex- 6
Hept- 7
Oct- 8
Non- 9
Dec- 10
Example: Name this compound and write its formula

Solution:
Name
• Only single bonds  Compound is an alkane This compound
• Three carbons  Prefix prop- is propane

Formula
• Count C’s and H’s  3 C’s & 8 H’s This formula is C3H8
Root prefix # of carbon
atoms You must memorize
Meth- 1 the root prefixes!
Eth- 2
Prop- 3 First four prefixes
But- 4 Meth- monkeys
Pent- 5
Eth- eat
Hex- 6
Prop- peeled
Hept- 7
Oct- 8 But- bananas
Non- 9
Dec- 10
Example:
Name the compound C2H6, and draw its structure.
Cyclic Hydrocarbons
 Carbons form a ring structure
 General formula (cyclic alkane): C nH2n
 Prefix: cyclo-

Example: cyclohexane, C6H12

Straight-Chain vs. Branched Hydrocarbons

Straight chain: Branched:

Carbons are arranged Some carbons branch
in one long chain off from a main
carbon chain
Branched Hydrocarbons:
Naming side chains

1. Identify the parent chain: The longest possible HC chain

2. Identify substituents (side chains or groups)

Common side chains include:

Alkyl groups (add –yl to prefix) Halide groups
CH3- methyl Br- (bromo)
CH3CH2- ethyl Cl- (chloro)
CH3CH2CH2- propyl F- (fluoro)
(CH3)2CH- isopropyl I- (iodo)
 There is a –CH3 group attached to the
octane chain: It is a methyl group

CH3
CH3-CH2-CH2-CH2-CH2-CH-CH2-CH3
The parent chain contains 8 carbons: It is octane
3. Number the parent chain, and indicate the carbon to which
the substituent group is attached.
 start counting from the end of the parent chain that gives the lowest
possible numbers

CH3
CH3-CH2-CH2-CH2-CH2-CH-CH2-CH3
8 7 6 5 4 3 2 1

This compound is: 3-methyloctane

substituent parent
If the same side chain appears more than once:
 indicate how many times it appears by using prefixes:
di = 2, tri=3, tetra=4

 number all carbons on the parent chain where groups are attached
separated by commas

CH3
CH3-CH-CH-CH2-CH2-CH2-CH2-CH3
1 2 3 4 5 6 7 8

CH3
This compound is: 2,3-dimethyloctane
If there are different groups attached:
 list them alphabetically in the name

ethyl groups
(C3, C4)
methyl
CH3 CH 3 group (C2)

CH2 CH2 CH3

CH3 – CH2 – CH2 - CH - CH - CH - CH3
7 6 5 4 3 2 1

This compound is: 3,4-diethyl-2-methylheptane

 Practice: Name this molecule

H 3C  parent chain: nine carbons

 two methyl groups
 one ethyl group

H 3C CH3

CH3

H 3C
Cl
Example: Cycloalkane with single substituent

Br

This compound is: bromocyclopentane

Notice a number is not required when
there is only one substituent group
 Example: Cycloalkane with multiple substituents
Start numbering C1 with lowest alpha substituent (ethyl >> methyl)

CH3 CH3

1 1

6 2 2 6
vs.

5 3 3 5

4 CH3 4 CH3
1-ethyl-3-methylcyclohexane 1-ethyl-5-methylcyclohexane

Which is correct??
Example: Cycloalkane as a substituent
Treat cycloalkane as a subtituent group if it is attached to a parent
chain that has more carbons.

H 3C CH3

CH3

This compound is: 6-methyl-3-cyclopropyldecane

alpha: methyl >> propyl
Isomers
Isomers are compounds that have the same
molecular formula, but different structures
Structural/Constitutional Isomers – Differ in the
connections and bonds within the molecule
All alkanes with 4+ carbons have structural isomers.

Example: C4H10

butane

methylpropane

Why isn’t this compound called 2-methylpropane??

 Practice! Name these molecules
A) B)
H3C CH2 H3C CH2 CH2 CH3
CH CH3
CH CH CH2 CH3
H2C CH2
H3C CH
CH3
CH3

C) CH3 CH3 CH3

CH3 CH2 CH CH CH CH2 CH CH3
CH2 CH3
Practice: Draw the structures below
A) 3-ethyl-2-methylpentane
B) 3-ethyl-1,5,5-trimethylcyclohexene
Practice: There are three distinct structural isomers for C5H12. Draw and name these.
Homework
Read p. 11-p.13 (Chemistry 12, Nelson)
Copy worked examples from text
Complete worksheets