ALKENE AND ALKYNE

 Saturated compounds (alkanes): Have the

maximum number of hydrogen atoms
attached to each carbon atom.

 Unsaturated compounds: Have fewer

hydrogen atoms attached to the carbon chain
than alkanes.

 Containing double bond are alkenes.

 CnH2n
 Containing triple bonds are alkynes.
 CnH2n-2
Alkene

 Hydrocarbons containing at least one C=C bond

 general formula: CnH2n
 Naming alkene

 Alkenes are named by finding the longest chain containing the double
bond and changing the name of the parent alkane from -ane to -ene

 root name + -ene suffix (compare root name + -ane suffix in alkanes)
 CH2=CH2 ethene (common name: ethylene)
 location of double bond indicated by the lowest-numbered carbon
atom involved in the bond.
Step 1

 Find the longest chain of carbons containing the

double bond. It contains six carbons.
Step 2-3
 Step 2 Name the parent chain. Its name is hexene.
 Step 3 Determine the position of the double bond in
the parent chain. In this case, you number the
parent chain from right to left because that gives
the first carbon of the double bond the lowest
number.
 The parent name is 2-hexene.
 Because the double bond takes priority over other substituents in an
alkene, sometimes the atoms of side chains and other functional
groups must receive higher numbers than they otherwise would.
 For example, 5-methyl-3-heptene is the correct name for the following
compound, not 3-methyl-4-heptene, even though the latter has a lower
number for the methyl group.
Step 4-5
 Step 4 Number and name the substituents.
 The compound has two methyl groups bonded to C4.
 Step 5 Put together all the pieces of the name.
 The compound's complete name is 4,4-dimethyl-2-
hexene.
 Polyene

 A type of organic compounds, called polyenes, contains two or

more double bonds.
 For example, dienes have two double bonds, and trienes have three.
 To name a diene or a triene, follow the same steps for naming an
alkene with these exceptions.
example

 Step 1 Determine the length of the parent chain and

the positions of the double bonds. The parent chain
is six carbons long. There are two double bonds,
and their positions are C1 and C4.
 Step 2 Write the numbers of
the locations of the double
bonds followed by a
hyphen: 1,4–.
 Step 3 After the hyphen
write the name of the parent
chain with the –diene
ending. The name of the
compound is 1,4-hexadiene.
Problem:

 Name each of the following molecules

Alkyne
 Hydrocarbons containing at least one C≡C bond
 general formula: CnH2n-2
 Structure of Alkyne

Alkynes contain a carbon—carbon triple bond.

Terminal alkynes have the triple bond at the end of the

carbon chain so that a hydrogen atom is directly bonded to a

carbon atom of the triple bond.
Internal alkynes have a carbon atom bonded to each carbon

atom of the triple bond.

Naming Alkyne
Alkynes are named in the same general way that
alkenes are named.
In the IUPAC system, change the –ane ending of

the parent alkane name to the suffix –yne.

 Choose the longest continuous chain that contains
both atoms of the triple bond
 Number the chain to give the triple bond the lower
number.
 Alkenes and alkynes are considered to have equal priority
 In a molecule with both a double and a triple bond, whichever is

closer to the end of the chain determines the direction of

numbering.
 In the case where each would have the same position number, the

double bond takes the lower number.

 In the name, “ene” comes before “yne” because of

alphabetization.
 Example :
Problem
 Write the IUPAC name for each of the
following unsaturated compounds:
Common Names
 Despite the precision and universal acceptance of IUPAC
nomenclature, some alkenes and alkyne (particularly
low-molecular-weight alkenes), are known almost
exclusively by their common names.
CH3
CH2 = CH2 CH3 CH= CH 2 CH3 C= CH2
IUPAC: Ethene Propene 2-Methylpropene
Common: Ethylene Propylene Isobutylene
Cis-Trans Isomers
 If alkenes have two different substituents at each end
of the C=C then they can exist as stereoisomers
because there is restricted rotation of the double bond.
 all terminal alkenes (begin or end with a C=CH ) do
2
not exist as cis- and trans- isomers.
 alkenes with the R-CH=CH-R unit can exist as cis-

and trans- isomers.

 Cis-trans isomerism is not possible if one of the double

bond carbons is attached to two identical groups.

 If two groups occur on the same side of the double
bond the compound is cis
 If they are on opposite sides the compound is trans
Example
 Name these following compounds:
CH3 CH3
C C
H CH2 CH3

Cl CH2 CH3
C C
H Cl
E, Z System
Br Cl

How to do?
H F

 Cis and Trans only describes disubstituted alkenes.

 Alkenes with non-identical groups on either side of the double bond
cannot be designated as cis or trans
 The E,Z system is used to describe when this occurs.
 E = entgegen, Z = zusammen
 E = Trans
 Z = Cis
 Rule 2. If the first atom don’t give you an answer
then move down the chain until you find a
difference.
 Rule 3. Multiple bonds atoms are equivalent
to the same number of single bonds.
Higher priority Br Cl Higher priority Br F

H F H Cl
Higher priority
(Z)-2-Bromo-1-chloro-1-floroethene (E)-2-Bromo-1-chloro-1-floroethene
Problem
 Name each alkene and specify its configuration
by the E,Z system.
Cl
(a) (b)

Cl
Cl
(c) (d)
Br
Physical Properties
Alkenes and alkynes have boiling points and melting points similar to
alkanes of comparable size. The unsaturated hydrocarbons are only
very slightly soluble in water and have densities less than water.

Melting Boiling Density

Point Point at 20°C
Name Formula (°C) (°C) (g/mL)
Ethyne HC CH -81 -84 (a gas)
Propyne CH3 C CH -102 -23 (a gas)
1-Butyne CH 3 CH2 C CH -126 8 (a gas)
2-Butyne CH3 C CCH3 -32 27 0.691
1-Pentyne CH 3 ( CH2 ) 2 C CH -90 40 0.690
1-Hexyne CH 3 ( CH2 ) 3 C CH -132 71 0.716
1-Octyne CH 3 ( CH2 ) 5 C CH -79 125 0.746
1-Decyne CH 3 ( CH2 ) 7 C CH -36 174 0.766
Reactions: Addition Reactions of Alkenes and
Alkynes

 Addition (combination) reactions have the form

A + B  AB
 For alkenes the general reaction has the form

R2C=CR2 + A-B  R2AC-CBR2

(where R = any alkyl group or H)
 Addition reactions are the most common types of reactions

for alkenes and alkynes

 The π bonds are easily broken, and that pair of electrons

can form a new  bond

 The reactions are favorable because the products (all 

bonds) are more stable than the reactants

Hydrogenation
 Adds a hydrogen atom to each carbon atom of a
multiple bond
 H2 can be added to alkenes or alkynes to form alkanes
 Usually a metal catalyst (Pt, Pd or Ni) is used to speed
up the reaction (the reaction generally doesn’t work
without a catalyst)
Examples:
H H

H 2C CH2 + H2 H H

H H

H H

HC CH + 2H2 H H

H H
Example
 What is the product of adding H2 (Ni catalyst) to 1-
butene?

 CH3CH2CH2CH3
Hydrohalogenation of Alkenes
 Hydrogen halides (HCl, HBr or HI) can add to alkenes to
form haloalkanes
 When a hydrogen halide adds to a substituted alkene, the

halide goes to the more substituted C (Markovnikov’s rule)

Examples:
H H H Br

C C + HBr H C C H

H H H H

H H H Cl

C C + HCl H C C H

H CH3 H CH3

CH3
CH
 Markovnikov’s rule
When adding HX to a double bond the
hydrogen of HX goes to the carbon
which already has the most hydrogens

..... conversely, the anion X adds to the

most
highly substituted carbon ( the carbon with
most alkyl groups attached).
Hydration: Addition of Water to Alkenes

 In the presence of a strong acid catalyst (HCl, H2SO4

etc.) alkenes react with H2O to form alcohols
 Hydration reactions follow Markovnikov’s rule

Examples:
H H Acid H OH
Cat.
C C + H 2O H C C H

H H H H

H CH3 Acid H OH
Cat.
C C + H 2O H C C CH3

H H H H

CH3
CH3 Acid
Cat. OH
+ H O
Halogenation of Alkenes and Alkynes

 Halogens (Cl2 or Br2) can add to alkenes or

Examples:
alkynes to form haloalkanes
 Alkenes
H H
form dihaloalkanes;
Br
alkynes
H
form
tetrahaloalkanes
C C + Br H C
2 C H

H H H Br

Examples:
Br
H H Br H
+ Br2
C C + Br2 H C C H

H H H Br Br

Br Br Br
H C C CH3 + 2Br2 H C C CH3
+ Br2
Br Br
Br
Take Home Message
 Oxidation of Alkene and alkyne
 Synthesis of Alkene and Alkyne
END