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Chapter 3
Alkenes: Structure, Nomenclature, and an Introduction to Reactivity

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FG03_00-02UN
Title
Ethene
Caption
Ethene is the hormone that causes tomatoes to ripen.
Notes
Keywords
FG03_00-03UN
Title
Alkenes
Caption
Hydrocarbons that contain a carbon-carbon double bond are called alkenes.
Notes
Many of the flavors, hormones, and insect pheromones belong to the alkene family.
Keywords
alkene,double,bond,hormones,pheromenes,flavors
FG03_00-04UN
Title
Muscalure and Farnesene
Caption
Muscalure is a pheromone in house flies and farnesene is found in the waxy coating on apple skins.
Notes
Muscalure is a long carbon chain that contains one double bond. Farnesene has branching on the carbon chain and contains four double bonds.
Keywords
muscalure,farnesene
FG03_00-05UN
Title
Alkane
Caption
Alkane/alkene, cyclic alkane/cyclic alkene
Notes
Keywords
FG03_00-06UN
Title
Molecular formula
Caption
Several compounds w/ molecular formula C8H14
Notes
Keywords
FG03_00-07UN
Title
Saturated hydrocarbon
Caption
Saturated hydrocarbon/ unsaturated hydrocarbon
Notes
Keywords
FG03_00-08UN
Title
Suffix-ene
Caption
The suffix for the double bond functional group is "ene."
Notes
The IUPAC name of an alkene is obtained by replacing the "ane" ending of the alkane with "ene."
Keywords
suffix,ene,alkene
FG03_00-09UN
Title
Numbering to indicate position
Caption
Numbering to indicate position of bond
Notes
Keywords
FG03_00-10UN
Title
Substituent chains
Caption
Numbering direction for substituent chains
Notes
Keywords
FG03_00-11UN
Title
Formula
Caption
3,6-dimethyl-3-octene/5-bromo-4-chloro-1-heptane
Notes
Keywords
FG03_00-12UN
Title
Formula
Caption
3-ethylcyclopentene/ 4,5- dimethylcyclohexene/ 4- ethyl-3-methylcyclohexane
Notes
Keywords
FG03_00-13UN
Title
Formula
Caption
2,3-dimethyl-4-octene/2-bromo-4-methyl-3-hexane
Notes
Keywords
FG03_00-14UN
Title
Formula
Caption
1,6-dichlorocyclohexene/5-ethyl-1-methylcyclohexene
Notes
Keywords
FG03_00-15UN
Title
Formula
Caption
2-bromo-4-ethyl-7- methyl-4-octene/6-bromo-3-chloro-4- methylcyclohexene
Notes
Keywords
FG03_00-16UN
Title
Vinylic/allylic carbons
Caption
Vinylic/allylic carbons
Notes
Keywords
FG03_00-17UN
Title
Vinylic/allylic groups
Caption
Vinyl group/allyl group, vinyl chloride/allyl bromide
Notes
Keywords
FG03_00-18P05a
Title
Formula
Caption
Prob.5 a
Notes
Keywords
FG03_00-19P05b
Title
Formula
Caption
Prob.5 b
Notes
Keywords
FG03_00-20P05
Title
Ring
Caption
Prob.5 c
Notes
Keywords
FG03_00-21P05d
Title
Formula
Caption
Prob.5 d
Notes
Keywords
FG03_00-22P05e
Title
Ring
Caption
Prob.5 e
Notes
Keywords
FG03_00-23P05f
Title
Formula
Caption
Prob.5 f
Notes
Keywords
FG03_00-24UN
Title
Carbon atoms
Caption
Six carbon atoms in the molecule are in the same plane
Notes
Keywords
FG03_00-25UN
Title
Pi Bonds
Caption
Orbital depiction of two p orbitals overlapping to form a pi bond.
Notes
The pi bond represents the cloud of electrons that is above and below the plane defined by the two sp2 carbons and the four atoms bonded to them.
Keywords
pi, bond, orbitals, overlapping, sp2
FG03_00-26P06a-d
Title
Ring compounds
Caption
PYB 01 : A-D ring compounds
Notes
Keywords
FG03_01
Title
Rotation about the Pi Bond
Caption
Rotation about the carbon-carbon double bond destroys the pi bond.
Notes
Since double bonds do not rotate, the cis and trans isomers cannot interconvert (except under extreme conditions).
Keywords
rotation, cis, trans, carbon-carbon, interconvert
FG03_01-01
Title
Cis and Trans 2-Butene Structures
Caption
Since there is no rotation around a double bond, an alkene can exist in two distinct forms, cis and trans.
Notes
The isomer with hydrogens on the same side of the double bond is called the cis isomer (cis is Latin for "on this side"), and the isomer with the hydrogens on opposite sides of the double bond is called the trans isomer (trans is Latin for "across").
Keywords
cis, trans, isomer, rotation
FG03_01-02UN
Title
sp2 carbon
Caption
sp2 carbon
Notes
Keywords
FG03_01-03UN
Title
Physical Properties of Cis and Trans Isomers
Caption
Cis and trans isomers are different compounds with different physical properties.
Notes
Boiling points and dipole moments differ among cis and trans isomers of alkenes.
Keywords
physical, properties, cis, trans, boiling, points, dipole, moments
FG03_01-04UN
Title
Interconversion
Caption
Cis-trans interconversion 2 pentene
Notes
Keywords
FG03_01-05
Title
Cis-trans Interconversion in Vision
Caption
When rhodopsin absorbs light, a double bond interconverts between the cis and trans forms.
Notes
Rhodopsin is bound to a very large protein molecule known as opsin. The structure of opsin is not shown in this figure.
Keywords
rhodopsin, light, interconverts, cis, trans
FG03_01-05-1P07b1
Title
Formula
Caption
PYB 02: CH3 compound
Notes
Keywords
FG03_01-06P07b2
Title
Formula
Caption
Prob.7 b.2
Notes
Keywords
FG03_01-06-1P07b3
Title
Formula
Caption
PYB 03: CH3 compound
Notes
Keywords
FG03_01-06-2P07b4
Title
Formula
Caption
PYB 04: CH3 compound
Notes
Keywords
FG03_01-06-3P08a-d
Title
Formula
Caption
PYB 04.5: A-D Cl compounds
Notes
Keywords
FG03_01-07UN
Title
Isomer
Caption
Which isomer is cis and which is trans?
Notes
Keywords
FG03_01-08UN
Title
Isomer
Caption
The z isomer/ the E isomer
Notes
Keywords
FG03_01-09UN
Title
Isomer
Caption
high priority for the Z and E isomers
Notes
Keywords
FG03_01-10UN
Title
Isomer
Caption
(Z) and (E) 1,2-Dichloro- 3-ethyl-4-methyl-2-Pentene
Notes
Keywords
FG03_01-11UN
Title
Hydroxy Methyl Group
Caption
E and Z nomenclature is used for compounds where the cis and trans system cannot be determined.
Notes
The Z isomer has the two groups of highest priority on the same side of the double bond. The E isomer has them on opposite sides of the double bond.
Keywords
E,Z,nomenclature
FG03_01-12UN
Title
Isobutyl group
Caption
Isobutyl group
Notes
Keywords
FG03_01-12-1P0901
Title
Formula
Caption
PYB 05: CH3 compound
Notes
Keywords
FG03_01-13P09a-2
Title
Formula
Caption
Prob.9 a.2
Notes
Keywords
FG03_01-14P09a-3
Title
Formula
Caption
Prob.9 a.3
Notes
Keywords
FG03_01-15P09a-4
Title
Formula
Caption
Prob.9 a.4
Notes
Keywords
FG03_01-16UN
Title
Ethene, cholesterol structures
Caption
Ethene/cholesterol structures
Notes
Keywords
FG03_01-17UN
Title
Electrophiles
Caption
Electrophiles
Notes
Keywords
FG03_01-18UN
Title
Nucleophiles
Caption
Nucleophiles
Notes
Keywords
FG03_01-19UN
Title
Alkyl Halide
Caption
A step-by-step process by which reactants are changed to products is called the mechanism of the reaction.
Notes
The pi bond in the alkene is most electron rich and will act as the nucleophile which will attack the electron poor hydrogen on the hydrogen bromide, the electrophile.
Keywords
mechanism,nucleophile,electrophile
FG03_01-19-1P11UN
Title
Formula
Caption
Prob.11
Notes
Keywords
FG03_01-20UN
Title
Double-barbed Arrow
Caption
Arrow with two barbs depicts motion of two electrons.
Notes
The tail of the arrow depicts the initial location of the electron pair. The head of the arrow depicts the final location of the electron pair.
Keywords
double-barbed, arrow, head, tail
FG03_01-21UN
Title
Single-barbed Arrow
Caption
Arrow with two barbs depicts motion of one electron.
Notes
The tail of the arrow depicts the initial location of the electron. The head of the arrow depicts the final location of the electron.
Keywords
single-barbed, arrow, head, tail
FG03_01-22UN
Title
2-butene/HBr Reaction
Caption
The mechanism can be seen more clearly if "curved arrows" are used to show the movement of the electrons.
Notes
The curved arrows are drawn to show how the electrons move as new covalent bonds re formed and existing covalent bonds are broken. The arrows are drawn from an electron-rich center to an electron-deficient center.
Keywords
curved,arrows,mechanism
FG03_01-23UN
Title
2-butene/HBr Reaction
Caption
The mechanism involves a carbocation intermediate which then act as the electrophile in the second step of the reaction.
Notes
The negatively charged bromine molecule from the hydrogen bromide, act as the nucleophile that attacks the electron poor carbocation (electrophile).
Keywords
carbocation,intermediate
FG03_01-24
Title
Curved Arrows (Correct/Incorrect)
Caption
A Few Words About Curved Arrows 1. (Correct/Incorrect)
Notes
Keywords
FG03_01-25UN
Title
Curved Arrows (Correct/Incorrect)
Caption
A Few Words About Curved Arrows 2. (Correct/Incorrect)
Notes
Keywords
FG03_01-26UN
Title
Curved Arrows (Correct/Incorrect)
Caption
A Few Words About Curved Arrows 3. (Correct/Incorrect)
Notes
Keywords
FG03_01-28P12a
Title
Formula
Caption
Prob.12 a
Notes
Keywords
FG03_01-29P12b
Title
Rings
Caption
Prob.12 b
Notes
Keywords
FG03_01-30P12
Title
Formula
Caption
Prob.12 c
Notes
Keywords
FG03_01-31P12d
Title
Formula
Caption
Prob.12 d
Notes
Keywords
FG03_01-32UN
Title
Formula
Caption
Y converted to Z
Notes
Keywords
FG03_01-33UN
Title
Reactants
Caption
Reactants/Products
Notes
Keywords
FG03_02
Title
Reaction Coordinate Diagram
Caption
A reaction coordinate diagram tracks the potential energy of a set of chemical species as they undergo one or more elementary reactions.
Notes
The dashed lines in the transition state indicate bonds that are partially formed or partially broken.
Keywords
reaction, coordinate, diagram, potential, energy, transition, state
FG03_02-01UN
Title
Equilibrium
Caption
The field of chemistry that describes the properties of a system at equilibrium is called thermodynamics.
Notes
When reactants form products, an equilibrium results that depends on the concentrations of reactants and products. The equilibrium constant, Keq, is equal to the relative concentrations of products and reactants at equilibrium.
Keywords
equilibrium,Keq,products,reactants
FG03_03
Title
Exergonic/Endergonic Reactions
Caption
Reaction coordinate diagrams for an exergonic reaction and an endergonic reaction.
Notes
A reaction in which the products are more stable than the reactants is an exergonic reaction. A reaction in which the products are less stable than the reactants is an endergonic reaction.
Keywords
exergonic, endergonic, reaction
FG03_03-00-1UN
Title
Josiah Gibbs
Caption
Josiah Gibbs: photo and biosketch
Notes
Keywords
FG03_03-00-2UN
Title
Henri Regnault
Caption
Henri Regnault: photo and biosketch
Notes
Keywords
FG03_03-01Sol11a
Title
Problem
Caption
Prob.11/Solved: solution to 11a
Notes
Keywords
FG03_03-02
Title
Entropy cartoon
Caption
Entropy cartoon
Notes
Keywords
FG03_03-03UN
Title
Bonds
Caption
Bonds broken and formed
Notes
Keywords
FG03_03-04UN
Title
Solvation of Anions and Cations by Water
Caption
The interaction between a solvent and a molecule or an ion in solution is called solvation.
Notes
For solvation of a positive charge by water, the partially negative-charged oxygen of water is attracted to the positive charge in solution. For solvation of a negative charge by water, the partially positive-charged hydrogen of water is attracted to the negative charge in solution.
Keywords
solvation, negative, positive, charge
FG03_04
Title
Reaction Coordinate Diagrams
Caption
Reaction coordinate diagrams for fast and slow exergonic reactions and fast and slow endergonic reactions.
Notes
The smaller the free energy of activation for a reaction, the faster the reaction takes place.
Keywords
activation, energy, reaction
FG03_04-01UN
Title
Reaction Rate Formula
Caption
Reaction rates are the product of the collision frequency and collision effectiveness.
Notes
Collision effectiveness requires sufficiently energetic particles to collide in the proper orientation for reaction to occur. Most collisions result in particles bouncing off of one another without undergoing reaction.
Keywords
reaction, rates, collision, frequency, effectiveness, orientation
FG03_04-02UN
Title
Simple First-Order Reaction
Caption
For a simple reaction where one particle is converted into product(s), the rate of the reaction is proportional to the concentration of reactant particles.
Notes
The reaction is said to be first-order in reactant if only one reactant particle is necessary for a reaction to occur.
Keywords
first-order, reaction, particles, concentration
FG03_04-02-1UN
Title
First-Order Rate Law
Caption
The proportionality constant which relates the rate of a reaction to the concentration(s) of reactant(s) is called the rate constant, k.
Notes
The rate constant is simply the rate of the reaction when all reactant concentrations are 1.0 molar.
Keywords
first-order, rate, law, constant, k
FG03_04-03UN
Title
Second-Order Reaction
Caption
The rate of a second-order reaction is proportional to the concentrations of two reactants multiplied together.
Notes
A second-order reaction involves two reactant particles colliding to undergo a chemical reaction. The two particles can be different kinds of particles, or they can be the same kind of particle (molecule, ion, etc.).
Keywords
second-order, reaction, rate, colliding
FG03_04-04UN
Title
Second-Order Reaction Involving Only One Kind of Reactant
Caption
A reaction in which two particles of the same substance collide with one another to undergo reaction is a second-order reaction.
Notes
The rate of a second-order reaction involving only one kind of reactant particle is proportional to the square of the reactant concentration.
Keywords
second-order, reaction, one, kind, particle, rate, square
FG03_04-05-1UN
Title
Forward rate
Caption
Forward rate=Reverse rate
Notes
Keywords
FG03_04-05-2UN
Title
Keq equation
Caption
Keq equation
Notes
Keywords
FG03_04-06UN
Title
Transition States
Caption
Bonds that break and bonds that form during the reaction are partially broken and formed during the transition state.
Notes
Atoms that become charges or lose their charge during the reaction are partially charged in the transition state.
Keywords
transition,state
FG03_05ab
Title
Steps in the Addition of HBr to 2-Butene
Caption
Reaction coordinate diagrams for the two steps in the addition of HBr to 2-butene.
Notes
The first step of the reaction involves the reactants forming an intermediate. The second step involves the intermediate proceeding to the products.
Keywords
HBr, 2-butene, intermediate, steps, addition
FG03_06
Title
Complete Reaction Coordinate Diagram for Addition of HBr to 2-Butene
Caption
Complete reaction coordinate diagram for the addition of HBr to 2-butene.
Notes
Transition states have partially formed bonds, whereas intermediates have fully formed bonds.
Keywords
HBr, 2-butene, intermediate, complete
FG03_06-01P25UN
Title
Problem 25
Caption
Three-Step Reaction Coordinate Diagram
Notes
Which step has the greatest free energy of activation? Is the first intermediate formed more likely to revert to reactants or go on to form products? Which step in the reaction sequence is rate-determining?
Keywords
three-step, reaction coordinate, diagram, problem, 25
FG03_11-26P27a
Title
Formula
Caption
Problems: 27 a
Notes
Keywords
FG03_11-27P27b
Title
Formula
Caption
Problems: 27 b
Notes
Keywords
FG03_11-28P27
Title
Ring
Caption
Problems: 27 c
Notes
Keywords
FG03_11-29P27d
Title
Formula
Caption
Problems: 27 d
Notes
Keywords
FG03_11-30P31a
Title
Problem
Caption
Problems: 31 a
Notes
Keywords
FG03_11-31P31b
Title
Problem
Caption
Problems: 31 b
Notes
Keywords
FG03_11-32P31
Title
Problem
Caption
Problems: 31 c
Notes
Keywords
FG03_11-33P31d
Title
Problem
Caption
Problems: 31 d
Notes
Keywords
FG03_11-34P31e
Title
Problem
Caption
Problems: 31 e
Notes
Keywords
FG03_11-35P31f
Title
Problem
Caption
Problems: 31 f
Notes
Keywords
FG03_11-36P32
Title
Formula
Caption
Problems: 32
Notes
Keywords
FG03_11-48P35a
Title
Formula
Caption
Problems: 35 a
Notes
Keywords
FG03_11-49P35b
Title
Formula
Caption
Problems: 35 b
Notes
Keywords
FG03_11-50P35
Title
Formula
Caption
Problems: 35 c
Notes
Keywords
FG03_11-51P35d
Title
Formula
Caption
Problems: 35 d
Notes
Keywords
FG03_11-59P39UN
Title
End-of-Chapter Problem 3.39
Caption
Three-step reaction coordinate diagram.
Notes
a. How many intermediates are there in the reaction? b. How many transition states are there? c. What is the fastest step in the reaction? d. Which is more stable, A or D? e. What is the reactant of the rate-determining step? f. Is the first step of the reaction exergonic or endergonic? g. Is the overall reaction exergonic or endergonic?
Keywords
three-step, reaction coordinate, diagram, end-of-chapter, problem, 3.39
FG03_00-CO
Title
Chapter Opener
Caption
Notes
Keywords

Title
Table 3.1 Homolytic Bond Dissociation Energies 
Caption
Notes
Keywords

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