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Saturated and
Unsaturated Hydrocarbons
Nomenclature of Alkenes
Nomenclature of Dienes
Nomenclature of Alkenes
Nomenclature of Alkenes
A number is not needed to denote the position of the C=C functional group;
it is always between C1 and C2.
Z = Zusammen (together)
E = Entgegen (opposite)
Relative Priorities
(E) 1-chloro-3-(chloromethyl)-4-ethyl-5-methylhex-3-ene
Double Bonds
lower
higher
Isotopes
Electrophiles
Nucleophiles
Reactive Intermediates
During the course of a reaction, a reactive
intermediate may be involved. We will limit our
study to the carbocation intermediate.
sp2, trigonal
planar
Empty p orbital
Increasing stability
Carbocation Stability
Alkyl groups:
decrease the concentration of positive charge on the carbon and
increase the stability of the carbocation.
hydrohalogenation
(transformation)
Learn to recognize
the functional group
transformation.
In this case it is an
alkene going to an
alkyl chloride
Me
Cl
HCl (g)
ether
Type: hydrohalogenation
Me
Reaction Mechanism
hydrohalogenation
(mechanism)
Ignore entropy G H
Reaction coordinate diagram
Bond Enthalpy
Endothermic or Exothermic
Bond
DH (kcal/mol)
Breaking
-bond
62
H-Br
88
COST
150
Bond Making
C-H
C-Br
GAIN
DH (kcal/mol)
101
71
172
Reactions in Chapter 4
name
class
1. Hydrohalogenation
electrophilic
addition
2. Hydration
electrophilic
addition
3. Halogenation
electrophilic
addition
4. Hydrogenation
electrophilic
addition
5. cis Di-hydroxylation oxidation
6. Oxidative cleavage oxidation
7. Epoxidation
oxidation
subclass
mechani
sm
hydrochlorination, yes
hydrobromination
, hydroiodination
yes
bromination,
chlorination
reduction
yes
no
no
no
no
Refer to the course map in the syllabus when studying the remainder
of the material in this course as we will not cover every reaction in the
textbook. Always refer to the 345 reactions summary in the course
materials folder in Blackboard. If the reaction has a yes under the
mechanism column, you are expected to learn the mechanism that
goes along with the reaction.