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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

1

Conjugated Dienes and Pericyclic Reactions

1,2- vs 1,4-addition, Diels-Alder cycloadditions, and molecular orbital theory governing these transformations.

2

Aromaticity and Aromatic Compounds

Hückel's rule, classifying aromatic/antiaromatic/nonaromatic systems, and understanding resonance stabilization energy.

3

Electrophilic Aromatic Substitution

Halogenation, nitration, sulfonation, Friedel-Crafts reactions, directing effects, and activating/deactivating substituent effects.

4

Nucleophilic Aromatic Substitution

Addition-elimination and benzyne mechanisms for replacing substituents on electron-deficient aromatic rings.

5

Reactions of Alcohols and Ethers

Alcohol conversions to halides, dehydration, oxidations (PCC, Jones, Swern), Williamson synthesis, and ether cleavage.

6

Epoxide Chemistry

Epoxide synthesis, ring-opening regiochemistry under acidic and basic conditions, and stereochemical outcomes.

7

Aldehydes and Ketones: Nucleophilic Addition

Grignard additions, hydride reductions, Wittig reactions, acetal formation, and cyanohydrin synthesis mechanisms.

8

Carboxylic Acids and Derivatives

Acyl substitution mechanisms, relative reactivity of esters, amides, anhydrides, and acid chlorides.

9

Enolate Chemistry and Carbon-Carbon Bond Formation

Aldol and Claisen condensations, Michael additions, malonic ester and acetoacetic ester syntheses.

10

Amines: Synthesis and Reactions

Amine preparation methods, reactions with nitrous acid, Hofmann elimination, and basicity considerations.

11

Spectroscopy and Structure Determination

IR functional groups, 1H/13C NMR chemical shifts and splitting, mass spectrometry fragmentation patterns.

12

Retrosynthetic Analysis and Multi-Step Synthesis

Disconnection approach, strategic bond breaking, protecting groups, and designing efficient synthetic routes.

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