Chemistry 2412: Organic Chemistry II Dr. Caroline Sheppard Summer 2015

Introduction to the course Roll Roll Short syllabus/syllabus on webpage Short syllabus/syllabus on webpage Course webpage Course webpage Course webpage Course webpage CHEM 2412 Lab: CHEM 2412 Lab: Starts today (introduction and syllabus) Starts today (introduction and syllabus) If taken previously and passed, don’t retake (see department head) If taken previously and passed, don’t retake (see department head)

Index Cards Index cards: Index cards: Name Name Major Major Plans after graduation Plans after graduation Job/hours work per week Job/hours work per week Hobbies, etc. Hobbies, etc. Grade you plan to earn in this class Grade you plan to earn in this class Anything else? Anything else?

CHEM 2411 Review What did you learn in Organic Chemistry I?

CHEM 2411 Review Chapter/sections from Klein (2 nd edition) you should already know: Chapter/sections from Klein (2 nd edition) you should already know: 1, 2, 3, 4, 5, 6, 7, 8, 10.2, , 13.1, 14.2, 14.11, 15.16, 18.2, 20.2, 21.2, 21.3, 21.6, , 2, 3, 4, 5, 6, 7, 8, 10.2, , 13.1, 14.2, 14.11, 15.16, 18.2, 20.2, 21.2, 21.3, 21.6, 23.2

CHEM 2411 Review Topics Drawing structures Drawing structures Lewis Lewis Condensed Condensed Line-angle Line-angle Functional groups Functional groups Alkane, alkene, alkyne, aromatic, alkyl halide, alcohol, ether, carbonyl, aldehyde, ketone, carboxylic acid, acid chloride, ester, amide, acid anhydride, amine, nitrile, thiol Alkane, alkene, alkyne, aromatic, alkyl halide, alcohol, ether, carbonyl, aldehyde, ketone, carboxylic acid, acid chloride, ester, amide, acid anhydride, amine, nitrile, thiol Nomenclature Nomenclature For all functional groups listed above For all functional groups listed above Isomerism Isomerism Constitutional Constitutional Stereoisomers Stereoisomers

CHEM 2411 Review Topics Structure Structure  an  bonds  an  bonds Bond strength Bond strength Primary, secondary, tertiary carbons Primary, secondary, tertiary carbons Bond and molecular polarity Bond and molecular polarity Physical properties Physical properties Intermolecular forces Intermolecular forces BP BP Solubility Solubility Hybridization Hybridization Atomic orbitals Atomic orbitals Hybrid orbitals Hybrid orbitals Which orbitals are used in sigma bonds? Pi bonds? Which orbitals are used in sigma bonds? Pi bonds?

CHEM 2411 Review Topics Resonance Resonance Resonance structures Resonance structures Which structures contribute to hybrid structure? Which structures contribute to hybrid structure? Electron movement Electron movement Acids and bases Acids and bases Brønsted-Lowry Brønsted-Lowry How to predict acid strength? How to predict acid strength? Lewis Lewis Alkane conformations Alkane conformations Staggered vs. eclipsed Staggered vs. eclipsed Torsional strain Torsional strain Steric strain Steric strain

CHEM 2411 Review Topics Cycloalkane conformations Cycloalkane conformations Angle strain Angle strain Cyclohexane chair vs. boat Cyclohexane chair vs. boat Alkene stability Alkene stability Cis or trans? Cis or trans? More substituted or less substituted? More substituted or less substituted? Stereochemistry Stereochemistry R and S R and S Chiral center (stereocenter), enantiomers, diastereomers Chiral center (stereocenter), enantiomers, diastereomers Meso compound Meso compound Racemic mixture Racemic mixture Cis and trans Cis and trans E and Z E and Z

CHEM 2411 Review Topics Mechanisms Mechanisms Symmetrical/homolytic/radical Symmetrical/homolytic/radical Unsymmetrical/heterolytic/polar Unsymmetrical/heterolytic/polar Nucleophile and electrophile Nucleophile and electrophile Electron motion Electron motion Energy diagrams Energy diagrams Reaction types Reaction types Addition Addition Elimination Elimination Substitution Substitution Rearrangement Rearrangement Oxidation Oxidation Reduction Reduction

CHEM 2411 Review Topics Radical reactions Radical reactions Halogenation of alkanes Halogenation of alkanes Mechanism steps, catalyst Mechanism steps, catalyst Substitution/Elimination reactions Substitution/Elimination reactions S N 1 S N 1 S N 2 S N 2 E1 E1 E2 E2

CHEM 2412 Start with alkenes (Chapter 9) Start with alkenes (Chapter 9) How to study for CHEM 2412? How to study for CHEM 2412?