Organic Chemistry PHS 2025
Fall 2013
Lecture Notes Section 3
Chapter 7: Alkenes: Structure & Reactivity
Define:
Alkene
Unsaturation
Degree of Unsaturation
Know:
How to determine degree of unsaturation
Naming Alkenes
Know:
How to name alkenes
Define:
Methylene group
Vinyl group
Allyl group
Cis-Trans Isomerism in Alkenes
Define:
Cis-Trans Isomers
Alkene Stereochemistry and the E,Z Designation
Define:
E,Z system
Know:
How to assign the E,Z conformation
Stability of Alkenes
Define:
Hyperconjugation
Know:
The stability of cis vs. trans conformations
Electrophilic Addition Reactions of Alkenes
Define:
Electrophilic addition reaction
Know:
Mechanism of electrophilic addition reaction
Energy diagram for electrophilic addition reaction
Orientation of Electrophilic Additions: Markovnikov’s Rule
Define:
Markovnikov’s Rule
Regiospecific
Know:
How to use Markovnikov’s rule to predict the product of an electrophilic addition reaction
Synthesize a compound using Markovnikov’s rule
Hammond Postulate
Define:
Hammond Postulate
Know:
How to use the Hammond Postulate to explain the relationship between the reaction rate and the
intermediate stability
Using the energy diagrams to explain Hammond Postulate
Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangement
Know:
The mechanism for a Hydride Shift
Chapter 8: Alkenes: Reactions and Synthesis
Halogenation of Alkenes: Addition of X2
Define:
Anti Stereochemistry
Bromonium Ion
Know:
The mechanism for the electrophilic addition of X2 across the double bond
Halohydrins from Alkenes: Addition of HOX
Define:
Halohydrins
Know:
The mechanism for the halohydrin formation
Hydration of Alkenes: Addition of H2O by Oxymercuration
Define:
Oxymercuration-Demercuration
Know:
The mechanism of the acid-catalyzed hydration of an alkene
The mechanism of the oxymercuration-demercuration hydration of an alkene
Hydration of Alkenes: Addition of H2O by Hydroboration
Define:
Hydroboration
Syn Stereochemistry
Know:
The mechanism of the addition of H2O by hydroboration
The mechanisms to create alcohols following the Markovnikov & anti-(non-) Markovnikov rule
Reduction of Alkenes: Hydrogenation
Define:
Hydrogenated or reduced
Reduction
Know:
The mechanism for hydrogenation of an alkene
The stereochemistry of the addition of the hydrogen across the double bond
Oxidation of Alkenes: Epoxidation and Hydroxylation
Define:
Oxidation
Glycol, 1,2-dialcohol or diol
Hydroxylation
Know:
The mechanism for the formation of an epoxide using mCPBA
The mechanism for the formation of an epoxide from a halohydrin
The mechanism for the formation of a trans-1, 2-diol
The mechanism for the formation of a cis-1,2-diol
Oxidation of Alkenes: Cleavage to Carbonyl Compounds
Define:
Ozonide
Know:
The mechanism for the Ozonolysis reaction
Predicting the reactant/product for an ozonolysis reaction
Addition of Carbenes to Alkenes: Cyclopropane Synthesis
Define:
Carbene
Know:
How to prepare cyclopropanes using the Simmons-Smith reaction
Radical Additions to Alkenes: Chain-Groth Polymers
Define:
Monomers
Polymers
Chain-Growth Polymers
Know:
The mechanism for the formation of chain-growth polymers
Reaction Stereochemistry: Addition of H2O to an Achiral Alkene
Know:
The mechanism for the product formation when reactant is achiral alkene
Reaction Stereochemistry: Addition of H2O to an Chiral Alkene
Know:
The mechanism for the product formation when reactant is chiral alkene
Chapter 9: Alkynes: An Introduction to Organic Synthesis
Naming Alkynes
Define:
Alkynes
Preparation of Alkynes: Elimination Reactions of Dihalides
Know:
The formation of alkynes via the elimination of dihalides
Reactions of Alkynes: Addition of HX and X2
Know:
The mechanism of alkyne additions with HX and X2
Hydration of Alkynes
Define:
Enol
Tautomer
Know:
The mechanism of the enol-keto tautomerism
The mechanism for the hydration of an alkyne
The mechanism for the hydroboration-oxidation of an alkyne
Reduction of Alkynes
Know:
The mechanism for reduction using Lindlar catalyst
The mechanism for reduction using lithium/ammonia
Oxidative Cleavage of Alkynes
Know:
The reaction using KMnO4 or O3 on an alkyne
Alkyne Acidity: Formation of Acetylide Anions
Define:
Acetylide Anion
Know:
Acidity of terminal alkyne, alkene, alkane
Alkylation of Acetylide Anions
Define:
Alkylation
Know:
The mechanism for the alkylation using the nucleophilic acetylide anion
An Introduction to Organic Synthesis
Define:
Retrosynthesis
Know:
How to plan the synthesis of an organic molecule via retrosynthetic method