Course Overview

General Course Information

This course introduces the organic structure and nomenclature, organized around functional groups. Organic reactions are presented with an emphasis on mechanisms, functional group interconversion, and simple synthetic schemes. The course also covers chemical transformations, physical properties, and laboratory techniques.

• Instructor: Brian Glaser

• Required Texts: Carey, 2011, Organic Chemistry, 12th edition

• Recommended: Klein, 2011, Organic Chemistry I: Translating the Basic Concepts

• Other Required Material: Scientific calculator, composition notebook

Course Structure and Grading

Grading Components

• Quizzes: 10%

• Exams: 40%

• Final Exam: 25%

• Laboratory Component: 25%

Grades are assigned using the following scale:

• 90–100%: A

• 80–89%: B

• 70–79%: C

• 60–69%: D

• <60%: F

Attendance is expected at every class meeting. Plagiarism will result in a zero for the assignment and may result in failure of the course.

Course Topics Outline

Main Topics

• Alkanes: Nomenclature, structure, and bonding

• Alkenes: Reactions and mechanisms

• Stereochemistry and stereoisomerism

• Alkyl halides: Preparation, reactions, and mechanisms

• Alcohols and ethers: Preparation, reactions, and mechanisms

• Electrophilic and nucleophilic aromatic substitution

Performance Objectives

First Unit: Chemical Bonding, Alkanes, Cycloalkanes

Students should be able to:

• Describe principles of atomic structure and chemical bonding (electron distribution, ionic bonding, covalent bonding).

• Write correct Lewis structures for molecules, with attention to formal charges and nonbonding electron pairs.

• Describe the concept of resonance and write resonance structures for molecules.

• Define molecular geometry using VSEPR theory.

• Write structural formulas for hydrocarbons (alkanes, cycloalkanes).

• Define and identify isomers (constitutional and stereoisomers).

• Recognize mistakes in proposed IUPAC names for alkanes.

• Write balanced equations for combustion reactions of hydrocarbons.

• Define conformational analysis and use Newman projection formulas.

• Draw chair conformations for cyclohexane and substituted cyclohexanes.

• Identify stereoisomers and explain differences from constitutional isomers.

Second Unit: Stereochemistry, Alkyl Halides, Alcohols, Ethers

Students should be able to:

• Define functional group and explain its importance in organic chemistry.

• Name alcohols and alkyl halides using IUPAC rules.

• Classify alcohols and alkyl halides as primary, secondary, or tertiary.

• Write mechanisms for reactions of alkyl halides and alcohols (e.g., with HX).

• Describe the stereochemistry of reactions (e.g., SN1, SN2, E1, E2 mechanisms).

• Use the Cahn-Ingold-Prelog system to assign R/S configurations to chiral centers.

• Calculate optical rotation and describe the physical properties of chiral molecules.

• Predict the relative rates of reactions of different substrates in SN1 and SN2 reactions.

Laboratory Schedule

Key Definitions and Concepts

Chemical Bonding

• Atomic Structure: The arrangement of electrons, protons, and neutrons in an atom.

• Covalent Bond: A chemical bond formed by the sharing of electron pairs between atoms.

• Ionic Bond: A chemical bond formed by the transfer of electrons from one atom to another.

• Resonance: The delocalization of electrons in molecules that have multiple valid Lewis structures.

• VSEPR Theory: Valence Shell Electron Pair Repulsion theory, used to predict molecular geometry.

Isomerism

• Constitutional Isomers: Compounds with the same molecular formula but different connectivity.

• Stereoisomers: Compounds with the same connectivity but different spatial arrangement.

• Chiral Center: A carbon atom bonded to four different groups, leading to non-superimposable mirror images.

• Optical Activity: The ability of a chiral molecule to rotate plane-polarized light.

Reaction Mechanisms

• SN1 Reaction: Unimolecular nucleophilic substitution, involves a carbocation intermediate.

• SN2 Reaction: Bimolecular nucleophilic substitution, involves a single concerted step.

• E1 Reaction: Unimolecular elimination, forms a carbocation intermediate.

• E2 Reaction: Bimolecular elimination, occurs in a single step.

Important Equations and Formulas

• General Combustion Reaction of Hydrocarbons:

• Rate Law for SN2 Reaction:

• Rate Law for SN1 Reaction:

Examples and Applications

• Example of Constitutional Isomers: Butane and isobutane () have the same molecular formula but different structures.

• Example of Stereoisomers: (R)-2-butanol and (S)-2-butanol are mirror images and differ in optical activity.

• Application: SN2 reactions are used in the synthesis of pharmaceuticals where stereochemistry is crucial.

Additional info:

• Some objectives and details were inferred from standard organic chemistry curricula and textbook organization.

• Laboratory schedule and performance objectives are typical for a first-semester organic chemistry course.