unit 3: reactions of alkenes. thermodynamics and kinetics hydrocarbons that contain only c-c bond...
TRANSCRIPT
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Unit 3: Reactions of Alkenes.Thermodynamics and Kinetics
Hydrocarbons that contain only C-C bond are called alkanes
Hydrocarbons that contain C=C bond are called alkenes or olefins (oil forming)
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尤加利樹油
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CH2 (CH2)n
AlkaneAlkane
CH3(CH2)nCH3
CnH2n+2
AlkeneAlkene
CHCH33(CH(CH22))nnCHCH33
CCnnHH2n2n
Cyclic alkaneCyclic alkane
CCnnHH2n2n
Cyclic alkeneCyclic alkene
CCnnHH2n-22n-2
H2C (CH2)n
HH
3.1 Molecular Formula and the Degree of Unsaturation3.1 Molecular Formula and the Degree of Unsaturation
Degree of unsaturation = 2Degree of unsaturation = 2
1 1 bond or 1 ring, degree of unsaturation = bond or 1 ring, degree of unsaturation = 11
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3.3 The Structure of Alkenes3.3 The Structure of Alkenes
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3.4 cis-trans3.4 cis-trans Isomerism Isomerism
Rotational barrier 63kcal/molRotational barrier 63kcal/mol
HH33C—CHC—CH33 rotational barrier = 2.9 kcal/mol rotational barrier = 2.9 kcal/mol
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Cis-Trans Interconversion in VisionCis-Trans Interconversion in Vision
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cis-transcis-trans Isomerism Isomerism
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3.6 Reactivity Considerations3.6 Reactivity Considerations
Functional group
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Organic ReactionsOrganic Reactions
• Electron-rich atoms or molecules are attracted to electron-deficient atoms or molecules
• Nucleophile: an electron-rich atom or molecule
• Electrophile: an electron-deficient atom or molecule
• A nucleophile and an electrophile react with each other
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Electrophiles and NucleophilesElectrophiles and Nucleophiles
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`
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Mechanism of the ReactionMechanism of the Reaction
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3.7 Thermodynamics and Kinetics3.7 Thermodynamics and Kinetics
Reaction coordinate digramReaction coordinate digram
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ThermodynamicsThermodynamics
The more stable the compound, The more stable the compound, the greater its concentration at equilibriumthe greater its concentration at equilibrium
Describes the properties of a system at equilibriumDescribes the properties of a system at equilibrium
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Gibbs standard free energy changeGibbs standard free energy change
This symbol indicates that the reaction takes place under standard conditionsThis symbol indicates that the reaction takes place under standard conditions--all species at 1 M, 25 --all species at 1 M, 25 OOC, and 1 atm.C, and 1 atm.↓↓
R is the gas constant (1.986 cal/mol OK)T is the absolute temperature (OK)
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Free Energy, Enthalpy and EntropyFree Energy, Enthalpy and Entropy
HHOO < 0, exothermic reaction; < 0, exothermic reaction; HHOO > 0, endothermic reaction > 0, endothermic reaction
In condensed phase, In condensed phase, SSOO ≈ 0. ≈ 0. Therefore Therefore GGOO ≈ ≈ HHOO
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Calculate Calculate HHOO for a Certain Reaction for a Certain Reaction
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p.130
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Solvation: Solvation: the interaction between a solvent and the interaction between a solvent and a molecule (or ion) in solutiona molecule (or ion) in solution
Solvation can have a large effect on the Solvation can have a large effect on the HHOO of a reaction, of a reaction, and it can also affect the and it can also affect the SSOO of a reaction. of a reaction.
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KineticsKinetics
Free energy of activationFree energy of activation
Deals with the rates of chemical reactions and the factors that affect those rates
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Rate LawRate Law
First-order reactionFirst-order reaction
Second-order reactionSecond-order reaction
Second-order reactionSecond-order reaction
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The Arrhenius equation:The Arrhenius equation:
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Rate Constant and Equilibrium ConstantRate Constant and Equilibrium Constant
A Bk1
k-1
At equlibrium, forward rate = reverse rate.At equlibrium, forward rate = reverse rate.
kk1 1 [A] = [A] = kk-1-1 [B] [B]
Keq =k1
k-1=
[B]
[A]
therefore
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Reaction Coordinate Diagram for the AdditioReaction Coordinate Diagram for the Addition of HBr to 2-Butenen of HBr to 2-Butene
Bonds being broken H = 61 kcal/molH-Br H = 87 kcal/molHtotal = 148 kcal/mol
Bonds being formed C-H H = 101 kcal/mol
Total Total H changeH change = +47 kcal/mol
Bonds being formed C-Br H = 69 kcal/mol
Over all Over all H changeH change = -22-22 kcal/mol
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Reaction Coordinate Diagram for the AdditioReaction Coordinate Diagram for the Addition of HBr to 2-Butenen of HBr to 2-Butene
-22 kcal/mol-22 kcal/mol
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3.8 General Mechanism for Electrophilic Addition3.8 General Mechanism for Electrophilic Addition
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3.9 Addition of Hydrogen Halides3.9 Addition of Hydrogen Halides
H2C CH2 + HCl CH3CH2Cl
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Relative Stabilities of CarbocationsRelative Stabilities of Carbocations
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sp2sp3
Inductive effectInductive effect
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Relative Stabilities of CarbocationsRelative Stabilities of Carbocations
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3.11 The Structure of the Transition State3.11 The Structure of the Transition State
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The Hammond postulateThe Hammond postulate
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3.12 Regioselectivity of Electrophilic Additio3.12 Regioselectivity of Electrophilic Addition Reactionsn Reactions
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Major productMajor product
Major productMajor product
Minor productMinor product
Minor productMinor product
Constitutional isomers
Regioselective reaction
H3CHC CHCH2CH3 + HBr H3CCH CH2CH2CH3 H3CH2C CHCH2CH3
Br
+Br
Non-regioselective reaction
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H3CH2CCH CH2 H3CH2CHC CH2
HH
vs
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3.13 Addition of Water and Alcohols3.13 Addition of Water and Alcohols
hydrationhydration
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Addition of Alcohol to AlkeneAddition of Alcohol to Alkene
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3.14 Rearrangement of Carbocations3.14 Rearrangement of Carbocations
According Markovnikov’ ruleThis compound should be major product
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Mechanism for the Formation of Rearranged ProductMechanism for the Formation of Rearranged Product
a secondary carbocationa tertiary carbocation
attack on unrearrangedcarbocation
attack on rearrangedcarbocation
minor product major product
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Mechanism for the Formation of Rearranged ProductMechanism for the Formation of Rearranged Product
major productminor product
attack on unrearrangedcarbocation
attack on rearrangedcarbocation
a secondary carbocation a tertiary carbocation
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Carbocation rearrangements also can occur by ring expansionCarbocation rearrangements also can occur by ring expansion
1,2-alkyl shift
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3.15 Addition of Halogens3.15 Addition of Halogens
p.154 last sentence
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unstable
F2 reacts explosively with alkenes!!!
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Formation of HalohydrinsFormation of Halohydrins
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3.18 Addition of Radicals.3.18 Addition of Radicals. The Relative Stabilities of Radicals The Relative Stabilities of Radicals
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Radical addition reactionRadical addition reaction
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Addition of HBr through Radical MechanismAddition of HBr through Radical Mechanism
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Addition of HBr through Radical MechanismAddition of HBr through Radical Mechanism
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3.19 Addition of Hydrogen.3.19 Addition of Hydrogen. The Relative Stabilities of Alkenes The Relative Stabilities of Alkenes
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Heat of HydrogenationHeat of Hydrogenation
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Relative Stabilities of AlkenesRelative Stabilities of Alkenes
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