CHEM 20273 – Organic

Reactions and Applications

University of Notre Dame
Fall 2023
Prof. Shawn Miller (he/him)
Logistics Note
• Canvas Quiz due tonight at 11:59 PM
• Second Midterm Exam is next Thursday
Recap
• The chemical properties of conjugated dienes are tied to the location
of the alkenes
• Molecular orbitals
• Electrophilic addition to conjugated dienes leads to multiple products
• Delocalized positive charge leads to multiple electrophilic carbon atoms
Lecture Learning Objectives
• By the end of this lecture, you will be able to…
• …explain the outcome of electrophilic addition to conjugated dienes including
with regards to product distribution.
• …predict and explain the outcome of cycloaddition reactions including
stereochemical and regiochemical concerns.
• …draw the mechanism for cycloaddition reactions.
• …explain how molecular orbitals determine the outcome of cycloaddition
reactions.
Thermodynamic vs. Kinetic Control
Exercise
Draw all products of the below chemical reaction. Identify the kinetic
product and the thermodynamic product.
Pericyclic Reactions
• Concerted reactions that proceed through a ring of electrons moving
in a closed loop with a cyclic transition state without ionic or radical
intermediates
Cycloaddition: The Diels-Alder Reaction
Cycloaddition Orbital Overlap
Stereospecificity
• The stereochemistry of the dienophile determines the
stereochemistry of the substituents in the ring
The Dienophile

R = H or alkyl
Regioselectivity
• If different regioisomers are possible, will there be selectivity?
Bonus Exercise
Predict the major product of the below chemical reactions. You do not
need to show stereochemistry.