Standard syllabus
Organic Chemistry I · Undergraduate · Chemistry
Topics
Structure and bonding
- Lewis structures, resonance, and formal charge in organic molecules
- Hybridization: sp³, sp², and sp carbon centers
- Bond lengths, bond angles, and molecular geometry
- Conformations of alkanes: Newman projections and energy diagrams
- Constitutional isomerism and stereoisomerism overview
- Chirality, enantiomers, and optical activity
- R/S configuration assignment using Cahn–Ingold–Prelog rules
- Diastereomers, meso compounds, and Fischer projections
- Newman and wedge-dash drawing conventions
- Intermolecular forces in organic compounds: London, dipole, H-bonding
Functional groups and nomenclature
- IUPAC nomenclature of alkanes, alkenes, and alkynes
- Naming alcohols, ethers, alkyl halides, and amines
- Functional group identification and priority rules
- Degree of substitution: primary, secondary, tertiary carbons
- Physical properties trends: boiling point, solubility, acidity
- Spectroscopic introduction: IR functional group regions
- ¹H NMR overview: chemical shift, integration, splitting (intro)
- Mass spectrometry: molecular ion and fragmentation patterns (intro)
- Index of hydrogen deficiency (degrees of unsaturation)
- Drawing and communicating organic structures clearly
Acid-base chemistry in organic systems
- Brønsted–Lowry acidity in organic molecules
- pKa trends: electronegativity, resonance, and inductive effects
- Carbanions and carbon acids (overview)
- Lewis acids and bases in organic reactions
- Solvent effects on acid-base equilibria
- Protonation and deprotonation in mechanism steps
- Ranking nucleophilicity and basicity
- Acid-base equilibria in biological contexts (preview)
- Grignard reagent formation as acid-base chemistry
- Using pKa tables to predict reaction direction
Substitution and elimination mechanisms
- Nucleophilic substitution: SN1 and SN2 mechanisms
- Stereochemical outcomes: inversion, racemization, retention
- Factors affecting SN1 vs SN2: substrate, nucleophile, solvent, leaving group
- Elimination reactions: E1 and E2 mechanisms
- Zaitsev's rule and regioselectivity in eliminations
- Competition between substitution and elimination pathways
- Carbocation rearrangements in SN1 and E1
- Neighboring group participation (where covered)
- Alkyl halide synthesis and reactivity
- Mechanism arrow notation and curved-arrow formalism
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