Organic Chemistry I

I. Introduction

Organic Chemistry is the chemistry of carbon-based molecules and the reactions that build, break, and rearrange their bonds. The course focuses on structure and bonding, functional groups, and reaction mechanisms. This course usually involves less memorizing and more pattern recognition.

II. Outline

1. Foundations: structure, bonding, and representation
   • Lewis structures, formal charge, resonance
   • Hybridization and geometry, bond polarity
   • Functional groups overview
   • Line-angle drawings, stereochemical notation
   • Acid–base basics for orgo
2. Conformations and stereochemistry
   • Newman projections; torsional strain and conformer stability
   • Cyclohexane chair forms, axial vs equatorial, and 1,3-diaxial interactions
   • Chirality, enantiomers, diastereomers, meso compounds
   • R/S configuration; optical activity
   • E/Z for alkenes
3. Mechanisms and curved-arrow logic
   • Nucleophiles/electrophiles; leaving groups
   • Electron-pushing rules
   • Carbocation, carbanion, radical stability trends
   • Reaction coordinate diagrams; kinetic vs thermodynamic control
4. Alkanes, alkenes, alkynes
   • Radical halogenation
   • Alkene reactions: additions (HX, hydration, halogenation, etc.)
   • Regioselectivity (Markovnikov/anti-Markovnikov) and stereoselectivity
   • Alkynes: acidity and addition patterns
5. Substitution and elimination
   • SN1 vs SN2
     • rate, stereochemistry, substrate effects
   • E1 vs E2, Zaitsev/Hofmann
   • Competition charts: how base strength, solvent, and substrate decide outcomes
6. Alcohols, ethers, and epoxides
   • Alcohol synthesis and transformations
   • Converting OH into better leaving groups
   • Epoxide opening
     • regioselectivity under acidic vs basic conditions
   • Protecting groups
7. Aromaticity and electrophilic aromatic substitution
   • Aromaticity rules and resonance stabilization
   • Benzene reactions
     • nitration, halogenation, Friedel–Crafts, etc.
   • Substituent effects: activating/deactivating, ortho/para vs meta directing
8. Carbonyl chemistry I: aldehydes and ketones
   • Carbonyl polarity and reactivity
   • Nucleophilic addition
   • Imine/enamine formation
   • Reduction and organometallic additions
9. Carbonyl chemistry II: carboxylic acids and derivatives
   • Acyl substitution logic: leaving group ability drives reactivity
   • Acid chlorides, anhydrides, esters, amides
   • Transesterification, hydrolysis, amidation
   • Decarboxylation and key special cases
10. Enols and enolates
    • Keto–enol tautomerism
    • Alpha acidity and enolate formation
    • Aldol concepts, condensation logic
11. Spectroscopy and structure determination
    • IR: functional group identification
    • 1 H NMR: chemical shift, integration, splitting (n+1), coupling
    • 1 3 C NMR basics; DEPT
    • Mass spectrometry: molecular ion, fragments
    • Strategy: combining data into a consistent structure

      III. Free Resources

    • OpenStax Organic Chemistry
      • Available as pdf and is pretty extensive (31 chapters).
    • Organic Chemistry LibreTexts
      • Many different choices of online textbooks.
    • NIST Chemistry WebBook
      • Reliable reference for physical properties and spectra for many compounds.

IV. Video Resources

• The Organic Chemistry Tutor (YouTube)
  • Problem-heavy walkthroughs for mechanisms, synthesis, and spectroscopy.
• Yale Open Courses – Freshman Organic Chemistry
  • Complete lecture series with strong emphasis on understanding reactivity patterns.
• MIT OpenCourseWare – Organic Chemistry
  • Full lecture materials (videos, notes, exams) for a more rigorous approach.
• Khan Academy – Organic Chemistry
  • Concept videos plus practice that cover most of a typical two-semester sequence.

V. Tools

Drawing Tools - Useful for sketching structures and checking geometry of molecules

• MolView (Molecule Viewer)
• MarvinJS
• PubChem Sketcher Databases
• PubChem
  • “The world’s largest collection of freely accessible chemical information”
  • You can search by many different factors.
• MassBank.eu - Spectral Database
  • “An Open-Source Mass Spectral Library for the Identification of Small Chemical Molecules of Metabolomics, Exposomics, and Environmental Relevance”
  • Open-Source Spectral Database
• Royal Society of Chemistry Periodic Table Virtual Labs
• Chem Collective
  • “Online simulation of a chemistry lab”

    VI. See Also

• Organic Chemistry II, General Chemistry II, General Chemistry I