Alkenes

Alkenes
Each member contains one double covalent bond
between two C atoms.
Draw condensed structural formulas of first three
members of alkenes family.

Alkenes are unsaturated aliphatic hydrocarbons.

Members of alkenes family create homologous series.

That means that every next member has extra -CH2- unit.
General formula : CnH2n

 What compound is the first member of alkene

family?

Can we have more than one double bond in a

carbon chain? If so, how would we call these
compounds?

Properties
Non-polar compounds - soluble in non-polar solvents
Gasses, liquids and solids
More reactive than alkanes, thanks to double bond

Naming Alkenes
Naming:

Substituents + number of C atoms + ene

prefix
root
suffix
Prefix: alkyl groups, halogens
Remember:
Suffix ene : tells you that one double bond is
present

Alkene Homologous Series

(C1-C2 double bond)
Name
(Root + ene)

# of C

Root

Condensed structural formula

Eth-

Ethene

Prop-

Propene

But-

1-butene

Pent-

1-pentene

Hex-

Hept-

Oct-

CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH = CH2

Non-

CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH = CH2

10

Dec-

CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH = CH2

Name
(Root + ene)

# of C

Root

Condensed structural formula

Eth-

Ethene

CH2 = CH2

Prop-

Propene

CH3 - CH = CH2

But-

1-butene

CH3 - CH2 - CH = CH2

Pent-

1-pentene

CH3 - CH2 - CH2 - CH = CH2

Hex-

1-hexene

CH3 - CH2 - CH2 - CH2 - CH = CH2

Hept-

1-heptene

CH3 - CH2 - CH2 - CH2 - CH2 - CH = CH2

Oct-

1-octene

CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH = CH2

Non-

1-nonene

CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH = CH2

10

Dec-

1-decene

CH3 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH2 - CH = CH2

Isomers
Branched differently (similar to alkanes) chain isomerism

Different position of double bond positional isomerism

Different position of groups around double bond cis-trans

isomers

Naming Alkenes
Step 1: Identify the longest continuous chain
that contains the double bond.
CH2= C CH2 CH2 CH3
I
CH2
I
CH3

CH2= C CH2 CH2 CH3

I
CH2
I
CH3

 Step 2: Number the parent carbon chain

beginning at the end nearest the double bond.
CH3 CH = CH CH2 CH3

CH3 CH = CH CH2 CH3

 If the double bond is in equal distance to both

ends of the parent chain
A) CH3 CH = CH CH2
l
Cl

B) CH2 CH = CH CH2
l
l
F
Cl

A) begin the numbering from the end closer to a

substituent.
B) begin the numbering from the end at which the
substituent is first in alphabetical order.

 Step 3: Identify and locate the branches.

Put branches in alphabetical order
Use multiplying prefixes (di-, tri-, tetra-..) if needed

Step 4: Put the name together

Sample Problem 1
1. CH3 CH = CH CH2 CH2 CH3
2.

CH3 CH2 CH2 CH2 CH = C CH3

CH2 CH2 CH3

3.

CH3 CH CH2 CH2 C = CH CH3

CH3
CH2 CH2 CH3

Sample Problem 1 - answers

1. 2-hexene
2. 4-methyl-4-nonene
3. 6-methyl-3-propyl-2-heptene

Sample Problem 2
1.

CH3 CH = CH CH2 CH CH3

l
F

2.

CH3 C = CH CH CH2 CH3

l
l
Cl
Br

3.

CH3 CH CH CH CH = C CH3
l
l
l

Br Cl
Cl
CH2 CH2 CH2 I

4.

CH3 CH2
F
l
I
CH3 CH CH CH C = C CH3

CH3 F
CH2 CH2 CH3

Sample Problem 2 - answers

1. 5-flouro-2-hexene
2. 4-bromo-2-chloro-2-hexene
3. 8-bromo-6,7-dichloro-1-iodo-4- methyl-4nonene
4. 4-ethyl2,5-difluoro-6-methyl-3-propyl-2heptene

Cis-Trans (Geometric) Isomers

Cis-trans isomers occur when different groups
of atoms are arranged around the double
bond.
The atoms around a single bond can rotate,
but the atoms around a double bond cannot
this will result in different geometric
structures.
How might you distinguish between two such
isomers in the lab?

Trans-Isomers

Cis-Isomers

Trans Isomer the two

larger groups attached to
the double bond are on
opposite sides of the double
bond
Ex. trans-2-butene

Cis Isomer the two larger

groups attached to the
double bonds are on the
same side of the double
bond
Ex. cis -2-butene

Sample Problems 3

Sample Problems 3 - answers

1.
2.
3.
4.

cis-3-heptene
trans-4-octene
cis-1,2-dichloroethene
It is not cis-trans isomer (propene)

Drawing Alkenes
Step 1: Identify the main chain and draw it as
skeletal structure.
Step 2: Number it. (Make sure that the double
bond is at the right spot.)
Step 3: Identify all substituents and attach them
to the parent chain.
Step 4: Fill in hydrogen atoms. (Remember to
count to four)

Sample Problems 4
Draw the following
1.
2.
3.
4.

4-methyl-2-pentene
3-ethyl-2,4-dimethyl-6-propyl-1-nonene
2,4-dichloro-3,3-dimethyl-1-butene
2-methylpropene *Why is there no number to
state the location of this double bond?

Sample Problems 4 answers