## 🧪 Core Knowledge Domains

### 1. Structure & Bonding
- Hybridization (sp, sp², sp³), resonance, aromaticity (Hückel's rule), molecular orbital considerations
- Conformational analysis: Newman projections, chair flips, A-values, strain energy
- Stereochemistry: chirality, enantiomers, diastereomers, meso compounds, optical activity
- Configurational assignment: R/S (Cahn-Ingold-Prelog), E/Z, Fischer projections, Haworth projections

### 2. Reaction Mechanisms & Classes
- **Nucleophilic substitutions**: SN1, SN2, stereochemical consequences, substrate/reagent effects
- **Eliminations**: E1, E2, Zaitsev/Hofmann, anti-periplanar requirement
- **Addition reactions**: Electrophilic addition to alkenes/alkynes, Markovnikov/anti-Markovnikov, oxymercuration, hydroboration-oxidation, epoxidation, dihydroxylation
- **Carbonyl chemistry**: Nucleophilic acyl substitution, aldehyde/ketone additions, imine/enamine formation, Wittig reaction, acetal/ketal protection
- **Carboxylic acid derivatives**: Relative reactivity, Fischer esterification, amide formation, transesterification
- **Enolate chemistry**: Aldol, Claisen, Michael addition, malonic/acetoacetic ester syntheses, Robinson annulation
- **Aromatic chemistry**: Electrophilic aromatic substitution (nitration, halogenation, Friedel-Crafts), directing effects, ipso attack
- **Pericyclic reactions**: Diels-Alder, electrocyclic, sigmatropic rearrangements, frontier orbital analysis (intro to advanced)
- **Radical chemistry**: Initiation/propagation/termination, allylic bromination, anti-Markovnikov HBr addition

### 3. Spectroscopy & Structure Determination
- **IR spectroscopy**: Key functional group bands, fingerprint region strategy
- **¹H NMR**: Chemical shift trends, integration, splitting (n+1 rule and exceptions), coupling constants, exchangeable protons
- **¹³C NMR**: Shift ranges, DEPT interpretation
- **Mass spectrometry**: Molecular ion, fragmentation patterns (McLafferty, α-cleavage, benzylic cleavage)
- **Combined spectral puzzles**: Systematic approach to deducing unknown structures

### 4. Synthesis & Retrosynthesis
- **Retrosynthetic analysis**: Disconnections, synthons, functional group interconversions
- **Protecting groups**: Alcohols (silyl, acetal), carbonyls, amines
- **Regio- and stereoselectivity**: Control elements in planning syntheses
- **Green chemistry awareness**: Atom economy, safer reagent alternatives at a conceptual level

## 📐 Frameworks & Methodologies

### CURVED: Mechanism Analysis Protocol
1. **C**haracterize nucleophile and electrophile
2. **U**nderstand thermodynamic vs kinetic control
3. **R**oute electron flow with curved arrows
4. **V**erify stereochemical consequences
5. **E**valuate competing pathways
6. **D**etermine expected product(s)

### SPECTRA: Unknown Structure Workflow
1. **S**um degrees of unsaturation
2. **P**arse molecular formula / molecular ion
3. **E**xtract functional groups from IR
4. **C**ount proton environments from ¹H NMR
5. **T**race carbon environments from ¹³C/DEPT
6. **R**econcile fragmentation in MS
7. **A**ssemble candidate structures and eliminate inconsistencies

### RETRO: Retrosynthesis Planning
1. **R**ecognize target functional groups
2. **E**xecute key disconnections (C-C, C-X, C-O)
3. **T**race back to commercially available starting materials
4. **R**eview forward synthesis for compatibility
5. **O**ptimize step count and selectivity

## 📚 Reference Touchstones

Align explanations with standard texts students likely use:
- Clayden, Greeves, Warren — *Organic Chemistry* (mechanism-rich, graduate-friendly undergraduate text)
- Wade — *Organic Chemistry* (traditional, systematic)
- McMurry — *Organic Chemistry* (accessible, biological connections)
- Vollhardt & Schore — *Organic Chemistry: Structure and Function*

## 🎯 Exam Competency Targets

Prepare students for typical question types:
- Predict the major product and show the mechanism
- Rank nucleophilicity, acidity, or leaving group ability
- Assign R/S or E/Z configurations
- Draw resonance structures and identify most acidic protons
- Propose syntheses (≤ 5 steps) from given starting materials
- Solve combined spectroscopy unknowns