CH 242 Organic Chemistry 2

Lecture Hours: 4
Credits: 4

Introduces the principles of organic chemistry for students majoring in physical or life sciences. Emphasizes structure, nomenclature, physical properties, chemical reactivities of organic molecules, mechanisms of reactions, and discussion of their biological or industrial importance. Stresses alcohols, ethers, free-radical reactions, aromatic compounds, spectroscopy, oxidation-reduction, aldehydes, and ketones.

Prerequisite: Placement into WR 115 (or higher), or completion of WR 090 (or higher); and completion of CH 241; or consent of instructor. (All prerequisite courses must be completed with a grade of C or better.)
Student Learning Outcomes:

Describe the structure, properties, nomenclature, synthesis and reactions of alcohols, ethers, aromatic hydrocarbons, aldehydes and ketones.
Explain the relationship between the structures of organic compounds and their subsequent physical and chemical properties.
Explain the bases of conjugation and aromaticity and illustrate their importance.
Use average bond dissociation energies to distinguish between completing mechanisms of a reaction.
Identify and illustrate the Diels-Alder Reaction.
Apply IR, NMR, and UV/VIS spectroscopy to structure determinations.
Recognize the organic chemistry basis of biologically important compounds and their reactions.
Translate the principles of organic chemistry into practical use in the organic laboratory.

Content Outline

Nucleophilic Substitutions and Eliminations
- Nucleophilic substitution: SN1 and SN2
- Stereochemistry and Walden inversion
- Kinetics
- Elimination reactions: E1 and E2
- Stereochemistry and Zaitsev’s Rule
- Elimination and cyclohexane conformations
- Deuterium isotope effect
- Substitutions in synthesis
Spectroscopy in Organic Chemistry
- The electromagnetic spectrum
- Mass Spectrometry
- Infrared Spectroscopy
Nuclear Magnetic Resonance spectroscopy
- Proton NMR
  - Nuclear spin
  - Shielding and deshielding and the chemical shift
  - Spin-spin splitting
- Carbon-13 NMR spectroscopy
  - DEPT C-13
Conjugated Systems
- Conjugated dienes; allyl systems & Resonance
- Reactions
  - 1,4-addition: Electrophilic Additions
    - kinetic vs. thermodynamic control
  - The Diels-Alder reaction
- Visible and ultraviolet spectroscopy
Benzene and Aromaticity
- The unique nature of benzene
- Huckel’s (4n + 2) rule
- Nomenclature
- Heterocyclic aromatic compounds
- Aromatic compounds in biochemistry
Electrophilic Aromatic Substitution Reactions
- General mechanism
- Reactions
  - Halogenation
  - Nitration
  - Sulfonation
  - Friedel-Crafts alkylation and acylation
  - Substituent effect
Alcohols and Phenols
- Properties
- Physical: hydrogen bonding, boiling points
- Chemical: acidity
- O-H bond cleavage reactions
- Acidity of phenols
- Synthesis
  - Oxymercuration-demercuration
  - Hydroboration
  - Organolithium and Grignard reagents
- Oxidation-reduction
  - Oxidation of alcohols
  - Reduction of carbonyl compounds
Ethers, Epoxides, Thiols, and Sulfides
- Physical properties
- Synthesis
  - Williamson Ether synthesis
  - Aldoxymercuration of alkenes
  - Acidic C-O bond cleavage reactions
- Epoxides
  - Ring opening reactions
  - Crown ethers
- Thiols and Sulfides
Alkehydes and Ketones: Nucleopilic Addition Reactions
- Naming
- Preparation
- Reactions
  - Oxidation
  - Nucleophilic Additions
    - Hydration
    - Cyanohydrin formation
    - Grignard reagents
    - Hydride reagents
    - Imine and Enamines
    - Wolff-Kishner
    - Acetals
    - Wittig
    - Cannizzaro
  - Conjugate additions
  - Biological applications