Module 3, 'Conformation and stereochemistry', discusses the varied three-dimensional shapes that molecules can assume because of rotational freedom around single bonds, or because of puckered ring structures. It also introduced the phenomenon called chirality that allows seemingly identical molecules to have very different biological and biochemical effects. We will focus on how to recognize and describe these 3D differences, and on why molecules with different chirality can have different effects on living organisms. Module 3 references chapter 3 of Soderberg.
Big ideas?
1. Rotational conformers have the same physical properties or function. 2. Stereoisomers can have profoundly different biological functions and effects. Module 3 slide sets: Conformation and stereochemistry
(Click on the links below to download each slide set for the lecture.) Introduction: Louis Pasteur and the discovery of molecular chirality 3.1: Conformations of open-chain organic molecules 3.2: Conformations of cyclic organic molecules 3.3: Chirality and stereoisomers 3.4: Labeling chiral centers 3.5: Optical activity 3.6: Compounds with multiple chiral centers 3.7: Meso compounds 3.8: Fischer and Haworth projections 3.9: Stereochemistry of alkenes 3.10: Stereochemistry in biology and medicine 3.11: Prochirality A: pro-R and pro-S groups on prochiral carbons B: The re and si faces of carbonyl and imine groups Resources for students:
> Module 3 lecture outline (PDF) > Module 3 lecture with instructor's notes (PDF) > Module 3 key concepts > Module 3 practice problems > Practice problems KEY Video tutorials for Module 3:
> Newman projection of ethane (Liverpool University) > Ethane conformations and Newman projections (fantzchem) > Newman projections - butane (Liverpool University) > Butane conformations (fantzchem) > Cyclohexane (Liverpool University) > Cyclohexane conformations (Khan Academy) > Chirality (Khan Academy) > Drawing enantiomers (Khan Academy) > Chiral molecules: R or S (Liverpool University) > Cahn-Ingold-Prelog system for naming enantiomers (Khan Academy) > Interactive model of (S)-thalidomide > Optical activity (Khan Academy) > Tartaric acid: Newman projections (Liverpool University) > Stereoisomers and friends (Khan Academy) > Stereochemistry: meso compounds, diastereomers (Professor Dave Explains) > Fisher projections (Khan Academy) > E-Z system (Khan Academy) > Pasteur's resolution of racemic acid: a sesquicentennial retrospect and a new translation (The Chemical Educator) > How Pasteur's artistic insight changed chemistry (Klein, NY Times, 14 Jun 2017) |
*Assignments:
> Homework set 3 > Reviewing ring conformations with origami WS > Modeling and cycloalkane conformations WS > Stereoisomer modeling WS > Sugar stereoisomer WS |