Organic Chemistry
Organic chemistry (“o-chem” or “orgo”) focuses on understanding the structure, properties, and reactivity of carbon-containing compounds. Over the course of two semesters, students learn the fundamentals of bonding, stereochemistry, and reaction mechanisms that underlie many chemical transformations in both living organisms and industrial processes.
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Semester 1
Organic Chemistry I
Structure, Bonding, and Resonance
Atomic orbitals and hybridization (sp, sp², sp³); Lewis structures, formal charges, and resonance; Molecular geometry and bond polarity
Alkanes and Cycloalkanes
Nomenclature (IUPAC rules); Physical properties and conformational analysis (Newman projections, chair conformations of cyclohexane); Ring strain, steric strain, and torsional strain
Stereochemistry
Chirality centers (R/S configuration); Enantiomers, diastereomers, and meso compounds; Optical activity and polarimetry
Alkyl Halides and Introduction to Reaction Mechanisms
Nomenclature and properties of alkyl halides; Nucleophilic substitution (SN1 and SN2); Elimination reactions (E1 and E2); Reaction mechanisms, rate laws, and transition states
Alkenes and Alkynes
Nomenclature (including cis/trans and E/Z); Electrophilic addition reactions of alkenes (e.g., hydrohalogenation, halogenation, hydration, hydroboration–oxidation); Concepts of regioselectivity (Markovnikov vs. anti-Markovnikov) and stereoselectivity; Introduction to alkyne reactions (hydration, hydrogenation, halogenation)
Acids and Bases in Organic Chemistry
Brønsted–Lowry and Lewis definitions; pKa values and their significance in organic mechanisms; How acid/base strength affects reactivity and reaction equilibria
Alcohols (Introductory Treatment)
Nomenclature and basic properties; Acid-base behavior of alcohols; Simple reactions (e.g., substitution to form alkyl halides)
Spectroscopic Methods (Introductory Overview)
Infrared (IR) spectroscopy basics (functional group identification); Mass spectrometry (MS) basics (molecular ion, fragmentation patterns); Proton Nuclear Magnetic Resonance (¹H NMR) fundamentals (chemical shift, integration, splitting)
Mechanistic Themes & Reaction Pathways
Arrow-pushing notation and mechanism steps (nucleophilic attack, proton transfers, leaving groups); Kinetic vs. thermodynamic considerations (where relevant)
Semester 2
Organic Chemistry II
Conjugation and Dienes
Conjugated systems, resonance, and stability; Electrophilic addition to conjugated dienes; The Diels–Alder reaction (cycloaddition mechanism)
Aromatic Compounds and Reactivity
Structure and stability of benzene (aromaticity criteria); Electrophilic aromatic substitution (EAS) mechanisms; Substituent effects (activating/deactivating groups, ortho/para/meta directors); Nucleophilic aromatic substitution (if time allows)
Carbonyl Chemistry: Aldehydes and Ketones
Nomenclature, structure, and properties; Nucleophilic addition mechanisms (e.g., formation of hydrates, hemiacetals, acetals); Oxidation and reduction (e.g., Tollens test, PCC, NaBH₄, LiAlH₄); Imine and enamine formation
Carboxylic Acids and Their Derivatives
Nomenclature and properties of acids, esters, amides, acid chlorides, anhydrides; Nucleophilic acyl substitution reactions; Saponification, transesterification, and hydrolysis of amides; Interconversion of acid derivatives
Enolates and Enolate Reactions
Keto–enol tautomerism; Aldol condensation, crossed aldol reactions; Claisen condensation, Dieckmann condensation; Michael addition and Robinson annulation
Amines and Nitrogen-Containing Compounds
Nomenclature and basic properties of amines; Basicity, alkylation, and formation of amides; Reductive amination and other amine synthesis methods
Advanced Spectroscopy
More detailed ¹H NMR (complex splitting patterns, coupling constants); ¹³C NMR basics (chemical shifts, DEPT); Advanced techniques (possibly 2D NMR, if time allows); Expanded use of IR, UV-Vis, and Mass Spectrometry in structure elucidation
Carbohydrates, Amino Acids, and Other Biomolecules (Introduction)
Basic structures of monosaccharides and disaccharides (if covered); Fischer and Haworth projections; Amino acid structure and properties; peptide bonds; Overview of lipids and nucleic acids (varies by course)
Synthesis Strategies
Multi-step synthesis combining reactions from both semesters; Retrosynthetic analysis (disconnection approach); Protecting groups and strategic reaction pathways