Organic Chemistry II Study Guide

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.