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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