Course Overview

Introduction to Organic Chemistry

Organic Chemistry is the study of the compounds of carbon, a field central to chemical, biological, and medicinal sciences. The course CHM 26100 covers fundamental principles, recurring themes, and mechanisms in organic chemistry, with a focus on structure-property relationships and spectroscopic techniques.

Course Structure and Schedule

Lecture Topics and Sequence

The course is organized into weekly lectures covering the following major topics:

• Structure and Bonding

• Acids and Bases; Functional Groups

• Structure and Stereochemistry of Alkanes

• The Study of Chemical Reactions

• Stereochemistry

• Alkyl Halides; Nucleophilic Substitution

• Structure and Synthesis of Alkenes; Elimination

• Reactions of Alkenes

• Alkynes

• Structure and Synthesis of Alcohols

• Reactions of Alcohols

• Infrared Spectroscopy and Mass Spectrometry

• Nuclear Magnetic Resonance Spectroscopy

Learning Outcomes

Key Skills and Knowledge

• Apply bonding, acid-base, kinetic, and thermodynamic principles to organic structures and reactions

• Recognize patterns of reactivity and shared reaction mechanisms

• Identify classes of molecules and understand structure-property relationships

• Use spectrometric and spectroscopic techniques for structure determination

• Plan multistep syntheses of organic molecules

• Understand the role of organic chemistry in industry and society

Grading and Assessment

Evaluation Components

• Homework assignments (10 x 25 pts)

• Assessments (3 x 175 pts)

• Comprehensive Final Assessment (350 pts)

• Lowest assessment score dropped

Grade cut-offs: A (≥ 870), B (869–740), C (739–600), D (599–460), F (0–459)

Assignment Schedule

Homework and Assessments

Assignments are scheduled throughout the semester, with due dates and point values clearly outlined. Three major assessments cover chapters 1–5, 6–10, and 11–13, with a comprehensive final at the end.

Reading Assignments

Weekly Reading from Wade & Simek

Students are expected to complete assigned readings before lectures. The schedule covers chapters 1–13, aligning with lecture topics and assessments.

Suggested Practice Problems

Chapter-Based Practice

Practice problems are recommended for each chapter to reinforce understanding and problem-solving skills. These problems cover key concepts such as bonding, structure, nomenclature, and spectroscopy.

Chapter 1: Structure and Bonding

Organic Chemistry Overview

Organic chemistry focuses on carbon compounds, which are central to life and industry. Carbon's ability to form single, double, and triple bonds, and its intermediate electronegativity, make it versatile in forming a wide variety of molecules.

Electron Configuration and Valence Electrons

The electron configuration of atoms determines their chemical behavior. The valence shell is the outermost electron shell, and valence electrons are those involved in bonding.

Lewis Dot Structures

Lewis dot structures represent atoms and their valence electrons. The element symbol stands for the nucleus and inner electrons, while dots indicate valence electrons. In molecules, valence electrons are distributed in available orbitals, often through hybridization.

Bonding Types and the Octet Rule

Atoms bond to achieve a stable electron configuration, often resembling the nearest noble gas. The main types of bonding are:

• Ionic bond: Electrostatic attraction between an anion and a cation

• Covalent bond: Sharing of electron pairs between atoms

• Polar covalent bond: Unequal sharing of electrons, resulting in partial charges

Electronegativity

Electronegativity (EN) is a measure of an atom's ability to attract electrons. The Pauling scale is commonly used, and EN generally increases from left to right across a period and from bottom to top within a group.

Formal Charge

Formal charge is a bookkeeping method to determine the distribution of electrons in a molecule. It helps identify which atom bears the most charge. The calculation is:

• Write the correct Lewis structure

• Assign each atom all its nonbonding electrons and half its shared electrons

• Compare this number to the atom's valence electrons in its neutral state

Formula:

Common Bonding Patterns

Organic compounds exhibit characteristic bonding patterns depending on the atom and its charge. Familiarity with these patterns is essential for recognizing unusual or incorrect structures.

Additional info: Work enough problems to become familiar with these bonding patterns so that you can recognize other patterns as being either unusual or wrong.