Organic Chemistry II Study Guide
The second semester of a two-semester undergraduate organic chemistry sequence: conjugated systems and aromaticity, electrophilic aromatic substitution, reactions of alcohols and ethers, oxidation and reduction, aldehydes and ketones (nucleophilic addition), carboxylic acids and derivatives (acyl substitution), enolate chemistry, amines, multi-step synthesis design, spectroscopy (IR, NMR, mass spec), and an introduction to biological molecules.
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12 Topics Covered
Conjugated Dienes and Pericyclic Reactions
1,2- vs 1,4-addition, Diels-Alder cycloadditions, and molecular orbital theory governing these transformations.
Aromaticity and Aromatic Compounds
Hückel's rule, classifying aromatic/antiaromatic/nonaromatic systems, and understanding resonance stabilization energy.
Electrophilic Aromatic Substitution
Halogenation, nitration, sulfonation, Friedel-Crafts reactions, directing effects, and activating/deactivating substituent effects.
Nucleophilic Aromatic Substitution
Addition-elimination and benzyne mechanisms for replacing substituents on electron-deficient aromatic rings.
Reactions of Alcohols and Ethers
Alcohol conversions to halides, dehydration, oxidations (PCC, Jones, Swern), Williamson synthesis, and ether cleavage.
Epoxide Chemistry
Epoxide synthesis, ring-opening regiochemistry under acidic and basic conditions, and stereochemical outcomes.
Aldehydes and Ketones: Nucleophilic Addition
Grignard additions, hydride reductions, Wittig reactions, acetal formation, and cyanohydrin synthesis mechanisms.
Carboxylic Acids and Derivatives
Acyl substitution mechanisms, relative reactivity of esters, amides, anhydrides, and acid chlorides.
Enolate Chemistry and Carbon-Carbon Bond Formation
Aldol and Claisen condensations, Michael additions, malonic ester and acetoacetic ester syntheses.
Amines: Synthesis and Reactions
Amine preparation methods, reactions with nitrous acid, Hofmann elimination, and basicity considerations.
Spectroscopy and Structure Determination
IR functional groups, 1H/13C NMR chemical shifts and splitting, mass spectrometry fragmentation patterns.
Retrosynthetic Analysis and Multi-Step Synthesis
Disconnection approach, strategic bond breaking, protecting groups, and designing efficient synthetic routes.
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