Alkenes Structure, Nomenclature, and An Introduction To Reactivity

Alkenes
Structure, Nomenclature, and an Introduction to Reactivity
Dra. Angelica Berenice Aguilar Guadarrama

Molecular Formula and the Degree of Unsaturation
CnH2n+2 CnH2n CnH2n CnH2n-2

The general molecular formula for a hydrocarbon is CnH2n+2 minus
two hydrogens p for every bond and/or ring in the molecule.
Several compounds with molecular formula C8H14

Determine the molecular formula for each of the following:
a. a 5-carbon hydrocarbon with one bond p and one ring
b. a 4-carbon hydrocarbon with two bonds p and no rings
c. a 10-carbon hydrocarbon with one bond p and two rings
d. an 8-carbon hydrocarbon with three bonds p and one ring
Determine the degree of unsaturation for the hydrocarbons with the

following molecular formulas:
C10H16 C20H34 C8H16 C12H20 C40H56
Determine the degree of unsaturation, and then draw possible structures,

for compounds with the following molecular formulas:
C3H6 C3H4 C4H6

Nomenclature of Alkenes

Draw the structure for each of the following compounds:
a. 3,3-dimethylcyclopentene c. ethyl vinyl ether
b. 6-bromo-2,3-dimethyl-2-hexene d. allyl alcohol
Give the systematic name for each of the following compounds:

The Structure of Alkenes
Cis–Trans Isomerism

a. Which of the following compounds can exist as cis–trans somers?
b. For those compounds, draw and label the cis and trans isomers.

The E,Z System of Nomenclature

Draw and label the E and Z isomers for
each of the following compounds:
Draw the structure of (Z)-3-isopropyl-2-

heptene.

How Alkenes React • Curved Arrows

Which of the following are electrophiles, and which are nucleophiles?

Use curved arrows to show the movement of electrons in each of
the following reaction steps:

Thermodynamics and Kinetics
Reaction Coordinate Diagrams

Thermodynamics
DG° = (free energy of the products) - (free energy of the reactants)

DG° = -RT ln Keq
DG° = DH° - TDS°
DH° = (energy of the bonds being broken) - (energy of the bonds being formed)
A reaction with a negative is called an exothermic reaction

A reaction with a positive is called an endothermic reaction
DS° = (freedom of motion of the products) - (freedom of motion of the reactants)

Kinetics

DG‡ = (free energy of the transition state) - (free energy of the reactants)
DG ‡ = DH ‡ - TDS ‡ the transition state) - (entropy of the reactants)

DH ‡ = (enthalpy of the transition state) - (enthalpy of the reactants)
DS ‡ = (entropy of the transition state) - (entropy of the reactants)

Reaction Coordinate Diagram for the Addition of HBr to 2-Butene

Addition of Hydrogen Halides

Carbocation Stability

List the carbocations in order of decreasing stability.

The Structure of the Transition State

Regioselectivity of Electrophilic Addition Reactions

Markovnikov’s rule: “When a hydrogen halide adds to an
unsymmetrical alkene, the addition occurs in such a manner that the
halogen attaches itself to the double-bonded carbon atom of the alkene
bearing the lesser number of hydrogen atoms.”
What would be the major product obtained from the addition of HBr to
each of the following compounds?

Addition of Water and Addition of Alcohols
mechanism for the acid-catalyzed addition of water

Addition of Alcohols

How could the following compounds be prepared,
using an alkene as one of the starting materials?

Rearrangement of Carbocations

Addition of Halogens

Oxymercuration–Reduction and Alkoxymercuration–Reduction
mechanism for oxymercuration

Addition of Borane: Hydroboration–Oxidation

Addition of Hydrogen • The Relative Stabilities of Alkenes
relative stabilities of alkyl-substituted alkenes

relative stabilities of dialkyl-substituted alkenes

Hydroxylation of Alkenes
mechanism for cis glycol formation

mechanism for cis glycol formation
Oxidative Cleavage of 1,2-Diols

Oxidative Cleavage of Alkenes
resonance contributors of ozone
mechanism for ozonide formation

Stereochemistry of Electrophilic Addition Reactions of Alkenes
Carbono asimétrico
HBr
CH3CH 2CH CH 2 CH3CH 2CHCH3 CH3CH 2CHCH3
+
Br
1-buteno Br-
2-bromobutano

Addition Reactions that Form One Asymmetric Carbon

What stereoisomers are obtained from each of the following reactions?

Addition Reactions that Form Products with Two Asymmetric Carbons
1. Addition Reactions that Form a Carbocation Intermediate or a Radical Intermediate
2. Stereochemistry of Hydrogen Addition

3. Stereochemistry of Hydroboration–Oxidation
4. Addition Reactions that Form a Bromonium Ion Intermediate


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Alkenes

Structure, Nomenclature, and an Introduction to Reactivity

Dra. Angelica Berenice Aguilar Guadarrama

CnH2n+2 CnH2n CnH2n CnH2n-2

Several compounds with molecular formula C8H14

Dra. Angelica Berenice Aguilar Guadarrama

Determine the degree of unsaturation for the hydrocarbons with the

Determine the degree of unsaturation, and then draw possible structures,

C3H6 C3H4 C4H6

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Give the systematic name for each of the following compounds:

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Draw the structure of (Z)-3-isopropyl-2-

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Reaction Coordinate Diagrams

Dra. Angelica Berenice Aguilar Guadarrama

DG° = (free energy of the products) - (free energy of the reactants)

A reaction with a negative is called an exothermic reaction

DS° = (freedom of motion of the products) - (freedom of motion of the reactants)

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

DG ‡ = DH ‡ - TDS ‡ the transition state) - (entropy of the reactants)

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

mechanism for the acid-catalyzed addition of water

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

mechanism for oxymercuration

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

mechanism for cis glycol formation

Dra. Angelica Berenice Aguilar Guadarrama

Oxidative Cleavage of 1,2-Diols

Dra. Angelica Berenice Aguilar Guadarrama

resonance contributors of ozone

mechanism for ozonide formation

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama

Dra. Angelica Berenice Aguilar Guadarrama