Course Introduction

Overview of Organic Chemistry

This course provides an introduction to the structure, bonding, and reactivity of organic (carbon-containing) compounds. Key concepts include three-dimensional chemistry (stereochemistry) and retrosynthetic analysis, which involves designing syntheses of organic compounds by thinking backwards.

• Stereochemistry: Study of spatial arrangement of atoms in molecules and its effect on chemical reactions.

• Retrosynthetic Analysis: Strategy for planning organic syntheses by breaking down target molecules into simpler precursor structures.

Strategies for Success

Problem-Solving Focus

Success in organic chemistry requires regular study habits and a deep understanding of concepts rather than rote memorization. The course emphasizes problem-solving over essays, and cumulative learning is essential.

• Read chapters ahead of time and attend lectures.

• Clarify points of confusion promptly with teaching assistants or the instructor.

• Practice problems regularly; recommended: one hour of problem-solving per hour of class.

• Utilize additional resources such as textbooks and solution manuals in the Chemistry Library.

Course Logistics

Pre-Requisites and Co-Requisites

• Pre-Requisites: General Chemistry I and II (Chem 1011 & 1021, Chem 1012 & 1022, or Chem 1151 & 1161).

• Co-Requisite: Organic Chemistry Laboratory (Chem 2412).

• If dropping the lecture (Chem 2411), you must also drop the lab (Chem 2412).

Class Schedule

• Monday-Wednesday, 12:00-1:30 PM in Chem 102.

• No class on certain holidays (Labor Day, Rosh Hashanah, day before Thanksgiving); recorded lectures will be provided.

Instructor and Office Hours

• Instructor: Professor Jeffrey Winkler

• Office Hours: Monday 4:00-5:30 PM, Wednesday 8:30-10:00 AM (starting Sept 10), and additional times as announced.

• Contact via email, but in-person discussion is encouraged for complex issues.

Textbook and Resources

• Textbook: Wade, Organic Chemistry, Ninth Edition, and Study Guide/Solutions Manual.

• Recommended: Molecular Visions molecular model kit.

• Online resources and additional textbooks available in the Chemistry Library.

Course Structure and Topics

Lecture Topics (Chronological Order)

• Structure and Bonding: Atomic structure, molecular orbitals, octet rule, covalent and ionic bonding, multiple bonding, hybridization, tetrahedral carbon, isomerism.

• Acids and Bases; Functional Groups: Nomenclature, acidity, resonance, inductive effects, identification of functional groups.

• Stereochemistry of Alkenes: Ethane, butane, torsional and ring strain, cyclohexane conformations, Newman projections, A values.

• Chemical Reactions: Halogenation, reaction kinetics, energies of halogenation, bromination, Hammond postulate, allylic bromination.

• Stereochemistry: Optical activity, R/S configuration, diastereomers, meso compounds, Fischer projections.

• Alkyl Halides: Nucleophilic substitution, leaving groups, nucleophiles, solvent effects, rearrangement reactions, E1/E2 mechanisms, Zaitsev's rule, alkene stability.

• Reactions of Alkenes: Addition reactions, anti-Markovnikov bromination, hydration, hydroboration, bromination, hydrogenation, epoxidation, epoxide opening, dihydroxylation, ozonolysis, oxidative cleavage, polymerization, metathesis, reduction-hydration, keto-enol tautomerism.

• Alcohols: Structure and synthesis, generation of alkoxides, Grignard reactions, reduction (LiAlH4, NaBH4), reactions with epoxides and acid chlorides.

• Reactions of Alcohols: Oxidation, Fischer esterification, pinacol rearrangement, Williamson ether synthesis.

Grading and Assessment

Exams and Quizzes

• Three one-hour exams (100 points each), with optional retake opportunities; higher score counts.

• Final exam (300 points), scheduled by the Registrar.

• In-class quizzes (participation-based, 5 points each, up to 90 points total).

• Course evaluations (10 points).

Grading Breakdown

• Final grade can be calculated as either 60% final/40% hour exams or vice versa, whichever is higher.

• Lecture grade (70%) + Organic laboratory grade (30%) = Final course grade.

• Grade cutoffs: ≥90% = A, ≥80% = B, ≥70% = C (with plus/minus distinctions).

Policies and Support

Academic Integrity

• Collaboration encouraged for homework; exams must be completed individually.

• Compliance with Penn's Code of Academic Integrity is required.

• Suspected misconduct will be referred to the Center for Community Standards & Accountability (CSA).

Course Drops, Withdrawals, and Incompletes

• Drop deadline: October 6

• Withdrawal deadline: November 3

• Pass/Fail grade change deadline: October 24

Academic Support and Disability Services

• Weingarten Center offers free, confidential academic support and tutoring.

• Disability Services provides reasonable accommodations for students with disabilities or medical conditions.

Additional info:

• Students are encouraged to use molecular model kits to visualize three-dimensional structures.

• Ed Discussion is used as an online forum for course content questions, not for grading or policy issues.

• Retake opportunities for hour exams are provided to maximize student success.