Organic Chemistry I: Course Syllabus, Structure, and Mechanism Guidelines

Course Overview

Introduction to Organic Chemistry

This course provides a comprehensive introduction to the structure, properties, and reactivity of organic compounds. It covers foundational concepts essential for understanding organic chemistry at the college level, including electronic structure, bonding, nomenclature, physical properties, and reaction mechanisms.

• Prerequisites: CHM 1450 and CHM 1480

• Textbook: Organic Chemistry by Paula Yurkanis Bruice (various editions), and Study Guide and Solutions Manual

• Supplemental Resources: ACS Study Guide available online

Main Topics and Chapter Structure

Ch. 1: Remembering General Chemistry: Electronic Structure and Bonding

Review of atomic structure, electron configuration, and types of chemical bonding relevant to organic molecules.

• Key Concepts: Atomic orbitals, hybridization, covalent and ionic bonds

• Example: Carbon hybridization in methane ($sp^3$)

Ch. 2: Acids and Bases: Central to Understanding Organic Chemistry

Explores acid-base reactions, equilibrium, and the effect of structure, substituents, and resonance on pKa.

• Key Concepts: Brønsted-Lowry and Lewis definitions, resonance stabilization, inductive effects

• Equation: $pK_a = - ext{log} K_a$

• Example: Acidity comparison between acetic acid and ethanol

Ch. 3: An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure

Covers systematic naming of organic compounds, their physical properties, and structural representations.

• Key Concepts: IUPAC nomenclature, functional groups, molecular geometry

• Example: Naming alkanes and alcohols

Ch. 4: Isomers: The Arrangement of Atoms in Space

Discusses structural, geometric, and stereoisomers, including chirality and optical activity.

• Key Concepts: Enantiomers, diastereomers, chiral centers

• Example: Stereochemistry of lactic acid

Ch. 5: Alkenes: Structure, Nomenclature, and an Introduction to Reactivity, Thermodynamics and Kinetics

Examines the structure and naming of alkenes, and introduces thermodynamic and kinetic principles in their reactions.

• Key Concepts: Alkene stability, Markovnikov's rule, reaction coordinate diagrams

• Equation: $E_a = ext{Activation Energy}$

Ch. 6: The Reactions of Alkenes: The Stereochemistry of Addition Reactions

Focuses on addition reactions to alkenes and the stereochemical outcomes.

• Key Concepts: Syn and anti addition, regioselectivity

• Example: Bromination of ethene

Ch. 7: The Reactions of Alkynes: An Introduction to Multistep Synthesis

Introduces the chemistry of alkynes and strategies for multistep organic synthesis.

• Key Concepts: Alkyne hydration, reduction, retrosynthetic analysis

Ch. 8: Delocalized Electrons: Their Effect on Stability, pKa, and the Products of a Reaction

Explores resonance, aromaticity, and electronic effects in organic reactions.

• Key Concepts: Resonance structures, aromatic stabilization, electronic effects

• Example: Benzene resonance

Ch. 9: Substitution and Elimination Reactions of Alkyl Halides

Details mechanisms, stereochemistry, and kinetics of substitution and elimination reactions.

• Key Concepts: $S_N1$, $S_N2$, $E1$, $E2$ mechanisms

• Equation: $ext{Rate}_{S_N2} = k[ ext{Alkyl Halide}][ ext{Nucleophile}]$

Ch. 10: Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

Examines the reactivity and mechanisms of functional groups beyond hydrocarbons.

• Key Concepts: Nucleophilic substitution, oxidation, reduction

Course Structure and Grading

Lecture and Exam Schedule

• Lectures held twice weekly

• Exams scheduled after major topic blocks (see syllabus for dates)

• Final exam covers all material

Grading Scale

Grade	Percentage
A	90 and above
A-	87-89
B+	83-86
B	80-82
B-	77-79
C+	73-76
C	70-72
C-	67-69
D+	63-66
D	60-62
F	below 60

Mechanism Guidelines

How to Write Organic Reaction Mechanisms

When asked to provide a mechanism, students should include structures for all energy minima, use proper arrow formalism, and ensure mass and charge balance. Mechanisms must clearly indicate the movement of electrons and the sequence of steps.

• Do not shortcut proton transfers.

• Use correct arrow formalism: Curved arrows for electron pair movement, fishhook arrows for single electrons.

• Balance each step: Ensure mass and charge are conserved.

• Indicate equilibrium and irreversible steps: Use $\rightleftharpoons$ for equilibrium, $\rightarrow$ for irreversible steps.

• Show evidence for step order: Indicate which steps are slow or fast.

• Account for stereochemistry: Show three-dimensional representations if necessary.

• Mark final products: Clearly indicate when the reaction is complete.

Example: Ester Hydrolysis Mechanism

Incorrect:

• Shows only equilibrium between reactants and products, omitting mechanistic steps.

Correct:

• Includes all intermediates, electron movement, and formation of products.

Assignments and Expectations

Preparation and Participation

• Read assigned textbook chapters before lectures.

• Complete assigned problems and review solutions.

• Active participation in lectures and office hours is encouraged.

Additional info:

• Course includes coverage of all major topics listed in the standard college organic chemistry curriculum.

• Mechanism guidelines are essential for success in exams and assignments.