Organic Chemistry

This page covers the topics and content covered in a first-semester undergraduate Organic Chemistry course (commonly referred to as Orgo or O-Chem). The material on this page is built on the principle that true mastery of O-Chem comes from active problem-solving rather than passive reading. Instead of dense text, these pages focus on building intuition for organic mechanisms and reactivity by guiding you through the standard problem types you'll face.

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Course Topics

Organic Chemistry 1 (First Semester)

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)

Organic Chemistry 2 (Second Semester)

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

We don't help with Orgo 2 by throwing forty new reactions at students and expecting them to keep it all straight. We group reactions into families that behave the same way, so a Grignard addition and a hydride reduction start looking like variations on one idea instead of forty separate ones. If you've ever had to memorize a synthesis route but froze when asked to work backward from the final product, we can help.