ALKENES

• Apply the basic rules of nomenclature of alkenes,

converting between structures and names and
vice versa.
 Alkene Structure

• Alkenes are also called olefins.

• Alkenes contain a carbon-carbon double bond.
• Terminal alkenes have the double bond at the end of the carbon
chain.
• Internal alkenes have at least one carbon atom bonded to each end
of the double bond.
• Cycloalkenes contain a double bond in a ring.

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 Alkene Hybridization

• Recall that the double bond consists of a  bond and a

 bond.
• Each carbon is sp2 hybridized and trigonal planar, with bond angles
of approximately 120°.

4
 Bond Dissociation Energy

• Bond dissociation energies of the C-C bonds in ethane (a

 bond only) and ethylene (one  and one  bond) can be used to
estimate the strength of the  component of the double bond.
• The  bond is much weaker than the  bond of a C-C double bond,
making it much more easily broken.
• Therefore, alkenes undergo many reactions that alkanes do not.

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 Cyclic Alkenes

• Cycloalkenes having fewer than eight carbon atoms have a cis geometry.
• A trans-cycloalkene must have a carbon chain long enough to connect the
ends of the double bond without introducing too much strain.
• trans-Cyclooctene is the smallest, isolable trans cycloalkene, but it is
considerably less stable than cis-cyclooctene, making it one of the few
alkenes having a higher energy trans isomer.

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7
Calculating Degrees of Unsaturation

ρ = (2 + 2C – H – X + N)
2

8
 Degrees of Unsaturation for Molecules
Containing Heteroatoms

How many degrees of unsaturation are there in a compound with the

molecular formula, C6H10OCl3N ?

Propose a skeletal structure for this compound.

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 Sample Problem

Calculate the number of degrees of

unsaturation for each molecular formula: (a)
C5H8O; (b) C6H11Cl; (c) C8H9N. Propose one
possible structure for each compound.
 Solution

a. 2
b. 1
c. 5
Possible structures:
a.

b.

c.
 Sample Problem

How many degrees of unsaturation are

present in each compound?
a. C6H6
b. C8H18
c. C7H8O
d. C7H11Br
e. C5H9N
 Sample Problem

How many degrees of unsaturation are

present in each compound?
a. C6H6
b. C8H18
c. C7H8O
d. C7H11Br
e. C5H9N
 CONCEPT CHECK

How many degrees of unsaturation are present in

each compound?
a. zolpidem (sleep aid sold as Ambien), C19H21N3O
b. mefloquine (antimalarial drug), C17H16F6N2O
15
 Naming Polyenes and Cyclic Alkenes

• Compounds with two double bonds are named as dienes by changing

the “-ane” ending of the parent alkane to the suffix “-adiene”.
• Compounds with three double bonds are named as trienes, and so forth.
• In naming cycloalkenes, the double bond is located between C1 and C2,
and the “1” is usually omitted in the name.
• The ring is numbered clockwise or counterclockwise to give the first
substituent the lower number.

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 Sample Problem
Give the IUPAC name for each alkene.
a. d.

b. e.

c.
 Naming Alkenes and Alkenols

• Compounds that contain both a double bond and a hydroxy group are
named as alkenols and the chain (or ring) is numbered to give the OH
group the lower number.

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 Sample Problem
Give the IUPAC name for each polyfunctional compound.
a.

b.

c.
 Cis and Trans Isomers of Alkenes

• Alkenes having one alkyl group bonded to each carbon atom can
be differentiated using the prefixes – cis and trans.
• cis has the two alkyl groups on the same side of the double
bond.
• trans has the two alkyl groups on opposite sides of the double
bond.

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21
 Sample Problem

Label each C=C double bond as E or Z. Kavain is a

naturally occurring relaxant isolated from kava root.
a.

b. C.
 Sample Problem

Draw the structure corresponding to each IUPAC name.

a. (Z)-4-ethylhept-3-ene

b. (E)-3,5,6-trimethyloct-2-ene

c. (Z)-2-bromo-1-iodohex-1-ene
 CONCEPT CHECK

Draw the structure of (2Z,6E)-3-ethyl-7-methyldeca-2,6-

dien-1-ol, the sex pheromone of the codling moth, a
common agricultural pest that destroys apple crops. By
spraying an apple orchard with this pheromone, the
mating of male and female moths is disrupted, and moth
populations can be controlled.
 Common Names of Alkenes
and Alkene Substituents

• Some alkene or alkenyl substituents have common names.

• The simplest alkene, CH2=CH2, named in the IUPAC system as
ethene, is often called ethylene.

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