16.CHM 123 - Alkenes

CHM 123
INTRODUCTION TO INORGANIC AND

ORGANIC CHEMISTRY
1
OBJECTIVES
• Students will be able to:
• Correctly name and draw the molecular
structure of alkenes
• Correctly identify, draw and name geometric
isomers
• Correctly name molecule given the structural
formula.
2
ALKENES
3
ALKENES
• C=C double bond
• Cn H2n - general formula
• unsaturated not "saturated" with maximum
hydrogens unsaturated fats have some double
bonds (easier to digest)
• note that cycloalkanes also are CnH2n
4
NOMENCLATURE
• Identify the longest continuous chain that
contains the C=C.
• Use the ending -ene to indicate the presence
of the C=C.
• Number the chain so that the first carbon of
the C=C reached has the lowest possible
number.
• Name and number substituents in the same
fashion as in alkanes.
5
NOMENCLATURE
6
NOMENCLATURE
• The alkene functional group takes precedence
over alkyl and halide functional groups.
The alcohol functional group takes

precedence over the alkene functional group.
7
NOMENCLATURE
8
NOMENCLATURE
• The alkene functional group takes precedence
over alkyl and halide functional groups.
The alcohol functional group takes

precedence over the alkene functional group.
9
NOMENCLATURE
10
ACTIVITY 1
Name the compound below
•CH3-CH2-CH=CH-CH2-CH2-CH3
Draw the structural formula of the molecule

below
•3-Hexene
11
ISOMERISM
12
ISOMERISM
13
ISOMERISM
14
GEOMETRIC ISOMERISM
15
ACTIVITY 2
• Draw the structure of cis-hex-3-ene
• Name the compound below
16
ISOMERISM
17
ISOMERISM
18
ISOMERISM
19
ISOMERISM
20
ISOMERISM
21
ISOMERISM
22
ISOMERISM
23
ISOMERISM
24
E/Z ISOMERISM
25
ACTIVITY 3
• Draw the structure of Z-2-hexene
HOME WORK
Z-3-hexene
E-2-hexene
E-2-hexene
26
OBJECTIVES
Students will be able to:
•Correctly determine the trends in physical
properties of alkenes given the molecules
•Correctly identify various techniques used to
prepare alkenes given the appropriate
conditions.
•Reproduce the mechanism for the preparation
of an alkene using dehydrohalogenation,
without error
27
PHYSICAL PROPERTIES
Physical state
The first lower member like ethene, propene and
butene are colorless gases.
 Alkenes with five to fifteen carbon atoms are
liquids and higher ones are solids at ordinary
temperatures.
Alkenes have characteristic smell.
Density
•Alkenes are lighter than water.
Solubility
•Alkenes are insoluble in water and soluble in
organic solvents such as benzene, ether etc.
28
PHYSICAL PROPERTIES
Boiling point
•The boiling points of alkenes gradually increase with
an increase in the molecular mass (or chain length).
This indicates that
•inter-molecular attractions become stronger with an
increase in the size of the molecule. Branched chain
alkenes have lower
•boiling points than the corresponding straight chain
isomers. This is because cis-isomers are polar
molecules and have higherboiling points when
compared to the trans-isomers. .
•cis-2-butene (b.p.= 3.7°C) and trans-2-butene (b.p.=
1°C) 29
PHYSICAL PROPERTIES
Melting point
•The melting points of alkenes increase with an
increase in the molecular mass. The trans-
isomers fit well into the crystal lattice
•due to their symmetrical structure. This results
in their melting at higher temperatures as
compared to the cis form.
30
PHYSICAL PROPERTIES
31
PREPARATION
• Preparations include the
 dehydration of alcohols
 dehydrohalogenation of alkyl halides
 dehalogenation of alkanes.
32
Dehydration of alcohols
In dehydration reactions,
•a molecule of water is eliminated from an
alcohol molecule by heating the alcohol in the
presence of a strong mineral acid.
•A double bond forms between the adjacent
carbon atoms that lost the hydrogen ion and
hydroxide group.
33
MECHANISM
Step1. Protonation of the alcohol.
Step2. Dissociation of the oxonium ion.
Step 3. Deprotonation of the carbocation.
34
Dehydrohalogenation of alkyl halides
• The dehydrohalogenation of alkyl halides,
another β elimination reaction, involves the
loss of a hydrogen and a halide from an alkyl
halide (RX).
• Dehydrohalogenation is normally
accomplished by reacting the alkyl halide with
a strong base, such as sodium ethoxide.
35
MECHANISM
1. A strong base removes a slightly acidic
hydrogen proton from the alkyl halide via an
acid-base reaction.
2. The electrons from the broken hydrogen-
carbon bond are attracted toward the slightly
positive carbon atom attached to the
chlorine atom. As these electrons approach
the second carbon, the halogen atom breaks
free, leading to the formation of the double
bond. The diagram below summarizes this
mechanism.
36
MECHANISM
37
DEHYDROHALOGENATION
38
Dehalogenation
Vicinal dihalides, which are alkane molecules
that contain two halogen atoms on adjacent
carbon atoms, can form alkenes upon reaction
with zinc.
39
PREPARATION
• Hydrogenation of Alkynes
 Catalyst: Pt, Pd or Ni
• Cracking
40
ACTIVITY
• Write reaction for the preparation of propene
from 1-propanol stating the appropriate
conditions.
from 1-Bromopropane stating the appropriate
conditions.
41
HOMEWORK
from 1,2-dibromopropane stating the
appropriate conditions.
42

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CHM 123

INTRODUCTION TO INORGANIC AND

The alcohol functional group takes

The alcohol functional group takes

Draw the structural formula of the molecule

• Draw the structure of Z-2-hexene

Step2. Dissociation of the oxonium ion.

Step 3. Deprotonation of the carbocation.

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