INTRODUCTORY MATERIAL

• Introduction
  • Tips for Success
    In order to get the most out of the laboratory experience, it is essential that you come prepared...
• Laboratory Safety Rules and Regulations
  • Laboratory Safety
    Occupational Safety and Health Administration (OSHA) regulations (29CFR1910.133) require that all persons in a chemical laboratory must wear suitable eye-protection at all times while in that laboratory...
  • Emergency Procedures
    Immediately alert your instructor to ANY accident or fire...
  • Laboratory Housekeeping Regulations
    Know your laboratory section number before coming to lab...
• Record-Keeping and Calculations
  • Forms
    Medical Information Form...
  • Miscellaneous Useful Calculations
    Few experiments will involve very complicated calculations...
• Techniques
  • Handling of Liquids, Calibration of Pasteur Pipet
    The various common operations that Organic chemists use regularly in the laboratory are called "Techniques"...
  • Pasteur Filter Pipet
    As mentioned earlier, when working with liquids on a small scale (e.g. 0.3 - 3.0 mL), it is never a good idea to pour...
  • Heating Reactions
    During the course of this semester, there will be many occasions to heat a reaction...
  • Melting Point
    Most solids have a characteristic temperature at which they change from the solid to the liquid state...

Some Important Functional Groups

Typical IR and ¹H NMR Values

EXPERIMENTS

• Experiment 1 - Literature Searching
  • Objective
    
    understand the benefit of doing research before working in the lab...
  • Introduction
    
    Organic chemistry boasts an incredibly long and fruitful research history...
  • Procedure
    
    You will pick a compound to research from the list at the end of this chapter...
  • Literature Search Report Form
    Download the Literature Search Report Form...
• Experiment 2 - NMR Spectroscopy
  • Objective
    
    to understand the important role of nuclear magnetic resonance spectroscopy in the study of the structures of organic compounds...
  • Introduction
    
    Spectroscopic methods are one of the more useful ways of structure determination in Organic Chemistry...
  • In-Lab Questions
    
    Download and print the following worksheet...
• Experiment 3 - Reduction of a Ketone
  • Objective
    
    To learn a versatile reaction for the reduction of a ketone (or aldehyde) to an alcohol.
  • Introduction
    
    The carbonyl group (C=O) found in aldehydes, ketones, carboxylic acids, esters, amides and other functional groups, plays a major role in determining the chemistry of these functional groups...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign.
  • Procedure
    
    In a 50 mL Erlenmeyer flask, dissolve about 0.500 g (note the actual amount used) of fluorenone in 8 - 10 mL of methanol...
  • In-Lab Questions
    
    Download and print the worksheet...
• Experiment 4 - Oxidation of Acetophenone
  • Objective
    
    to demonstrate a simple application of the "Iodoform" reaction...
  • Introduction
    
    The haloform reaction is characteristic for methylketones as well as for alcohols (e.g. ethanol, 2-propanol), that can be oxidized to methyl carbonyl compounds...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign.
  • Equation
    
  • Procedure
    
    Using a dispensing pipet, carefully add 180 µL of acetophenone to a clean 6" Test Tube. Measure 6.3 mL of household bleach (e.g., "CLOROX"^TM) in a 10 mL graduated cylinder and carefully add it to the same test tube, followed by 0.5 mL of 10% NaOH...
  • In-Lab Questions
    
    Download and print the worksheet...
• Experiment 5 - Nitration of Methyl Benzoate
  • Objective
    
    to demonstrate "Electrophilic Aromatic Substitution"...
  • Introduction
    
    This reaction is a typical example of "Electrophilic Aromatic Substitution"...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign.
  • Procedure
    
    A 1.0 mL sample of conc. Sulfuric Acid is placed in a clean, dry 6" Test Tube and cooled to about 0°C...
  • In-Lab Questions
    
    Download and print the worksheet...
• Experiment 6 - Aldol Condensation
  • Objective
    
    To provide experience with Aldol condensation, a useful reaction to prepare conjugated carbonyl systems.
  • Introduction
    
    Hydrogen atoms that are located on a carbon adjacent (alpha) to a carbonyl group are acidic and can be removed by base...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign...
  • Procedure
    
    In a small Erlenmeyer flask, mix 2 mL of the sodium hydroxide solution with 2 mL of 95% ethanol...
  • In-Lab Questions
    
    Download and print the following worksheet...
• Experiment 7 - Preparation of 1,4-diphenyl-1,3-butadiene
  • Objective
    
    To provide experience with the "Wittig Reaction", one of the most versatile reactions available for the synthesis of an alkene.
  • Introduction
    
    The carbon-carbon double bond, the "Functional Group" of all alkenes, is a very common functionality...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign...
  • Procedure
    
    [adapted from: S. W. Breuer, J. Chem. Educ. 1991, 68, A58-A60.]...
  • In-Lab Questions
    
    Download and print the worksheet...
• Experiment 8 - Amide Preparation
  • Objective
    
    In this experiment, the amide, 2-(N-acetylamino)benzoic acid (N-Acetylanthranilic acid) will be prepared by the reaction of 2-aminobenzoic acid (anthranilic acid) with acetic anhydride.
  • Introduction
    
    Amides are another one of the many functional groups encountered in the study of Organic Chemistry...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign...
  • Procedure
    
    Make sure that the reaction is performed under the sink hoods (i.e., not out in the middle of the bench top)...
  • In-Lab Questions
    
    Download and print the following worksheet...
• Experiment 9 - Arenediazonium Salts
  • Objective
    
    In this experiment, the use of one of the more specialized aromatic reactions, diazonium salts, is examined.
  • Introduction
    
    During the study of the chemistry of aromatic compounds, several reactions are encountered that allow for halogenation (Cl and Br only), nitration, alkylation, and acylation of the aromatic ring...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign...
  • Procedure
    
    In a 50 mL Erlenmeyer flask, 0.5 g of ethyl 4-aminobenzoate (benzocaine) is dissolved in 8 mL of water containing 2 mL of 6 M HCl...
  • In-Lab Questions
    
    Download and print the following worksheet...
• Experiment 10 - Hydrolysis of Glycerol Tristearate: Preparation of Soap
  • Objective
    
    In this experiment a triglyceride will be hydrolyzed in order to prepare glycerol plus the salt of the corresponding fatty acids (soap).
  • Introduction
    
    Soap is produced by the saponification (hydrolysis) of a triglyceride (fat or oil)...
  • Pre-Lab
    
    Complete the pre-lab assignment in WebAssign.
  • Procedure
    
    Place 0.18 g of glycerol tristearate in a 5 mL conical vial...
  • In-Lab Questions
    
    Download and print the following worksheet...

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