CHEM 20273 – Organic

Reactions and Applications

University of Notre Dame
Fall 2023
Prof. Shawn Miller (he/him)
Logistics Note
• Problem-Solving Set due tomorrow at 11:59 PM
• Canvas Quiz due Wednesday at 11:59 PM
• Second Midterm Exam is next week
Recap
• Spectroscopy allows us to learn about a molecule
• Determine an unknown structure
• Monitor a chemical reaction
• From chemical reactions we’ve discussed in the past, we know π bonds
can act as nucleophiles (alkenes and alkynes)
• Those π bonds have been “isolated”
• What happens if we put π bonds next to each other?
Lecture Learning Objectives
• By the end of this lecture, you will be able to…
• …choose reaction conditions that create conjugated dienes.
• …explain the relationship between diene conjugation and their molecular
orbitals.
• …predict and explain the outcome of electrophilic addition to conjugated
dienes.
π Bond Terminology

“allene”
Diene Synthesis and Fundamental Information
• We want to see alkenes, we do elimination reactions
Molecular Orbitals Review
atomic orbitals

C C
Molecular Orbitals and Conjugation
Molecular Orbitals and Conjugation
Electrophilic Addition to Conjugated Dienes
Exercise
For this question, assume the indicated alkene reacts first. Draw all
possible products that result from the indicated alkene reacting.
Electrophilic Addition to Conjugated Dienes
Thermodynamic vs. Kinetic Control
Exercise
Draw all products of the below chemical reaction. Identify the kinetic
product and the thermodynamic product.