Hydrocarbons: organic molecules composed of

HYDROGEN and CARBON.

There are 3 types of straight-chain hydrocarbons:

A hydrocarbon that has only single

Alkane
bonds between carbon atoms

A
A hydrocarbon
hydrocarbon that
that contains
contains at
at
Alkene
Alkene least
least one
one carbon-carbon
carbon-carbon double
double
bond
bond
A
A hydrocarbon
hydrocarbon that
that contains
contains at
at
Alkyne
Alkyne least one carbon-carbon triple bond
least one carbon-carbon triple bond
 Representations of an organic compound:

1. Complete structural diagram

 shows all the atoms in a structure and the
way they are bonded to one another

2. Condensed structural
diagram
 shows the bonds between the carbon
atoms but not those between the carbon
and hydrogen atoms

3. Line structural diagram

 shows only lines representing bonds
between carbon atoms
 # of
Name Formula Diagram
Carbons
 
 
1 Methane  

  
  
2 Ethane   

  
  
3
3 Propane
Propane   

 
 
 
 
4
4 Butane
Butane
 
 

 
 
 
5
5 Pentane
Pentane
 
 
 

 
  

6
6 Hexane
Hexane
  
 
 # of
Name Formula Diagram
Carbons
 
 
7 Heptane  

  
  
8
8 Octane
Octane   

 
 
 
 
9
9 Nonane
Nonane
 
 

 
 
 
10
10 Decane
Decane
  
 
 IUPAC Naming System

Naming Organic Compounds follows this

basic format:

Prefix (branches off main chain) + root parent name

(main chain) + suffix (end of word)

All deviations (either multiple bonds or atoms other

than hydrogen and carbon) are indicated by prefixes
or suffixes according to a specific set of priorities
 Naming Alkanes

1. Determine the longest chain of carbons.

The chain does not have to be in a straight horizontal
line. The parent name ends in "ane" and the prefix
indicates the number of carbon atoms in the main
chain. Identify all the branches (substituents)
attached to the parent chain
 Naming Alkanes

2. Number the carbons.

Number the carbons starting with the end closest to a branch. The
objective is to have the smallest numbers for the branches. Check
left to right and right to left numbering.

If there are two branches equidistant from each end of the longest
chain, number the carbons starting at the end closest to the next
branch.

If the branches are symmetrically distributed, number the carbons

at the end which is closest to the branch with alphabetic priority.
 Naming Alkanes

3. Name the branches.

The branch name is written as a prefix to the parent
name forming one word. The number of the carbon
to which the branch is attached is written in front
separated by a hyphen.

When naming a branch, the alkane name has its

“-ane” ending changed to “-yl”. A 1-carbon branch is
called methyl. A 2-carbon branch is called ethyl. A 3-
carbon branch is called propyl.
 Note: hyphens and commas

A number and a name are separated by a hyphen. Two

numbers are separated by a comma.

If there are more than one of the same branch attached to the
main chain, use the appropriate prefix to indicate the number
of identical branches: di (2), tri (3), tetra (4), etc. along with a
position number, regardless of redundancies
 
If there are different branches, the names go in alphabetical
order. When determining alphabetical order of the branches,
the actual branch name determines the order not the prefix
(except iso and cyclo which are included in alphabetizing)
Example 1: Name the following compounds:

CH3 – CH2 – CH2 – CH3 butane

Note: alphabetical order CH3

1 2 3 4
CH3 – CH2 – CH – CH – CH2 - CH3
5
4-ethyl-3-methylheptane CH2
6
CH2
7
CH3
 Example 1: Name the following compounds:

1 2 3 4 5 6

3- ethyl-2,4- dimethyl hexane

Note: prefixes are not included in alphabetical order

1 2 3 4 5 6 7 8

3,6- dimethyl- 4-prop-2-yl octane

 CH3
3-ethyl-5-methylheptane
│
CH3 ─ CH2 ─ CH ─ CH2 ─ CH ─ CH2 ─ CH3
│
CH2
│
CH3
Note: ethyl has priority over methyl (alphabetical)
 Draw the condensed structural diagram for
3-ethyl-2,2-dimethylhexane

CH3
CH3 – C – H
C –C
H2 – HC2 –HC3
CH3 CH2 –CH3
 Draw the line diagram for
6-ethyl-2,5-dimethyl-4-prop-1-ylnonane
 Structural Isomers

Compounds that have the same molecular formula, but different


 
structures
 Different shape and bonding, different properties
 C4H10

 
 Alkyl Halides

 Alkanes in which one or more hydrogen atoms

have been replaced by halogen atoms
 Use the prefix fluoro- , chloro- , bromo-, or iodo-
with a position number
 Name in alphabetical order
 Alkyl Halides

Br
CH3– CH – CH - CH3 2-bromo-3-chlorobutane
Cl
 Cycloalkanes:

Not all alkanes are based on straight chains. Their

carbon atoms can form rings. A cyclic alkane is a
closed loop.

When naming these molecules, the cyclic structure is

always the main chain

Number the carbons, in either direction, so that the

branches have the lowest possible position number
 Cycloalkanes

1. Determine the number of carbons in the ring only.

 This is the root. Add the prefix "cyclo" and the appropriate
ending "ane" or "ene"
2. Numbering for cycloalkanes:
One branch only: The branch is always on carbon #1, but the
number is not included in the name.
Two branches: Carbon # 1 is determined by alphabetical order
of the branches. The carbons are numbered in the direction to
give the lowest numbers for the branches.
3. Numbering for Cycloalkenes:
The double bond starts on carbon #1. Number in the direction
to give the lowest branch numbers.
 Name the following:

CH3
CH2CH3

1-ethyl- 2,4-dimethylcyclohexane
CH3
Draw 2-ethyl-1,4-dimethylcyclohexane

6
CH3
5 1

4 2
3
CH3 CH2CH3
Alkenes and Alkynes
 Alkenes and Alkynes

Alkenes contain one or more double bonds and have

a general formula of CnH2n
Alkynes contain one or more triple bonds and have a
general formula of CnH2n-2
Since alkenes and alkynes are NOT bonded to the
maximum possible number of atoms, these
compounds are often referred to as unsaturated
hydrocarbons

Reactivity:
alkynes > alkenes > alkanes
 Naming Alkenes

1. Determine the longest chain which contains the double

bond. The number of carbons in the chain determines
the root name and the suffix becomes "ene".

2. Number the carbons starting at the end closest to the

double bond. If the double bond is equidistant from both
ends, number the carbons based on the closest branch.

3. Indicate the position of the double bond using the lower

numbered carbon in that bond. The number is placed
before the suffix separated by a hyphen.
 Notes:

 When there is only one possible structure for the double

bond placement, the number is considered redundant and
is not included.
 When a hydrocarbon contains more than one double bond,
this information must also be indicated in the
nomenclature. The ending "ene" represents one double
bond.
 If there are more double bonds, a prefix is used before the
ending "ene" such as "diene" (2 double bonds) or "triene"(3
double bonds).
 Alkynes: named using the same rules as alkenes except
that the parent chain ends in “yne”
 Name the following:

* double bonds have priority

CH 3

CH 3 CH CH CH CH 3
5 4 3 2 1

4- methyl pent -2- ene


Location of double bond
CH 3 CH 2 C H 2 C CH 2 CH 3
6 5 4 3
3- ethylhex-2-ene CH CH 3
2 1
* main chain must include double bond
 * 2 double bonds

C H 2 CH C CH C H 2 C H 3
1 2 3 4 5 6

C H
C H 3 C H CH
3 3

3- propan-2-ylhex-1,3-diene
 * ethyl before methyl

CH 2 CH 3 CH 3

CH 3 CH 2 CH C C C H CH 2 CH 3
1 2 3 4 5 6 7 8

3- ethyl-6- methyl oct-4-yne

CH3C(CH3)2CH(CH2CH3)CCH

CH3 CH2 – CH3

CH3 – C – CH – C  CH
5 4 3 2 1
CH3
3-ethyl-4,4-dimethylpent-1-yne
 Draw the following:
3-methylpent-2-ene
CH3
CH3 – H
C =C–C
H2 – C
H3
2,5,7-trimethyl-5-prop-1-yloct-3-yne

CH3 CH3 CH3

CH3 CH C C C CH2 CH CH3

CH2 CH2 CH3

 •Do not need to # double bond
Name the following: (it has to be between 1 & 2)

3,4-dimethylcyclopent-1-ene 2
CH3
1 3

3,4-dimethylcyclopentene 5 4

Draw the following:

CH3
3,3-diethyl-2-methylcyclopentene
CH3
1
5 2
4 3
CH2CH3
CH2CH3
 Steroisomers (Cis- Trans Isomers)

 Compounds that have the same molecular formula, but different

arrangements of atoms in space around the carbon-carbon
double bond
 Same number of atoms, with the double bond in the same
position, but with a different 3-D geometry around that double
bond
 Cis means that the two groups are on the same side of the
double bond
 Trans indicates that they are on ‘opposite’ sides
 
 
 
 
 Cis-Trans Isomerism

Alkenes cannot have cis-trans isomers if a carbon

atom in the double bond is attached to identical
groups
 Aromatics

 Aromatic compounds are those derived from benzene (C6H6)

and similar ring systems. If the benzene takes priority the
nomenclature is the same as with aliphatic hydrocarbons,
however the parent becomes “benzene”. If the benzene does
not take priority the benzene substituent is named “phenyl”.
 1. The parent name is benzene
Note: When specific branches are added to the benzene ring,
the parent name changes to the historical common name.
There are a number of these compounds.
 2. A branch is added as a prefix. Additional
branches are:

  Br – bromo

Cl – chloro
F – fluoro
I – iodo
 – nitro
3. No number is required for one branch because the
branch is always considered to be on the first
carbon. Two branches require the carbons to be
numbered or a prefix indicating the position of the
branches
4.  Numbering the carbons
 Numbers are used such that carbon #1 has the
priority branch and the branch numbers are the
lowest possible.
5.  Benzene ring as a branch: The branch name is
"phenyl“(-C6H5).
 When it is attached to is 6 carbons or longer
 If the chain it is attached to has a double or triple
bond, or other functional groups
 CH3 methylbenzene (toluene)
(no number is required for one branch
– it is always on the 1st carbon)

CH2CH3
CH3
1-ethyl-2,4-dimethylbenzene

CH3
When a benzene ring has only 2 branches, the prefixes –
ortho, –meta, and –para can be used instead of
numbers
 Sometime the benzene ring is not the main chain.
 When this occurs, the benzene ring branch is known as phenyl
(-C6H5)

CH3CH2CHCH2CH2CH3 3-phenylhexane

Draw the following aromatic structures:

1-chloro-2-methylbenzene 3-phenylbut-1-ene
Cl
CH2=CHCHCH3
CH3