Recommended CER Experiments
to accompany
Hornback’s Organic Chemistry, Second Edition
The table below matches sections from the book with recommended CER labs. Click on the experiment title to view a PDF of
each lab. Go to www.CERLabs.com to search the complete CER database and to learn more about customizing your lab
manual through CER. To access password-protected material, like instructor’s resources and printable review copies on this
site, contact Rebecca Heider for a password.
Chapter Title
2. Organic Compounds:
A First Look
Recommended Experiment(s) from CER
ANAL 735: Catalytic Hydrogenation of Unknowns
6. Stereochemistry I
Cis-Trans Isomers and
Conformations
SYNT 719: Brominating Alkenes
7. Stereochemistry
II
Chiral Molecules
SYNT 719: Brominating Alkenes
REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid
REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid
ANAL 751: Enantiomeric Purity of Commercial Ibuprofen
TECH 752: Resolving a Racemic Mixture: Using (-)-Proline to Separate (±)-Phenylsuccinic Acid
REAC 714: Studying SN1 and SN2 Reactions: Nucleophilic Substitution
8. Nucleophilic
Substitution Reactions KINE 733: The Kinetics of Solvolysis of 2-Chloro-2-Methylpropane
Reactions of Alkyl
Halides, Alcohols, and
Related Compounds
2
9. Elimination
Reactions
Reactions of Alkyl
Halides, Alcohols, and
Related Compounds
REAC 712: Dehydrating Cyclohexanol
REAC 736: The Pinacol Rearrangement
SYNT 713: Preparing Isopentylacetate by the Fischer Esterification
SYNT 725: Oxidizing Methoxybenzyl Alcohol to Methoxybenzaldehyde Using Phase Transfer Catalysis
10. Synthetic Uses of
Substitution and
Elimination Reactions
Interconverting Functional
Groups
SYNT 726: Two Methods for the Synthesis of Phenacetin
SYNT 738: Copper-Catalyzed Oxidation of Benzoin to Benzil
REAC 742: Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol
SYNT 745: Synthesizing Aspirin: The Acetylation of Salicylic Acid
SYNT 746: Acetaminophen: The Acetylation of p-Aminophenol
REAC 747: Hydroboration and Oxidation of 1Hexene to Make 1Hexanol
11. Additions of
Carbon-Carbon Double
and Triple Bonds
Reactions of Alkenes and
Alkynes
SYNT 719: Brominating Alkenes
REAC 742: Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol
REAC 747: Hydroboration and Oxidation of 1Hexene to Make 1Hexanol
REAC 716: Nitrating Acetanilide or Methyl Benzoate: Electrophilic Aromatic Substitution
17. Aromatic
Substitution Reactions SYNT 723: Friedel-Crafts Acylation: Synthesis of 4-Methoxyacetophenone
SYNT 724: Friedel-Crafts Alkylation: Kinetic versus Thermodynamic Control
SYNT 748: Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence
REAC 749: Nucleophilic Aromatic Substitution: The Reaction of 3,4-Dichloronitrobenzene with Sodium Methoxide
18. Additions to the
Carbonyl Group
Reactions of Aldehydes
and Ketones
REAC 715: Reducing Benzil Using Sodium Borohydride
SYNT 718: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde
REAC 721: Synthesis of Trans-9-(2-Phenylethenyl)Anthracene: A Wittig Reaction
SYNT 743: Converting Benzaldehyde to Benzilic Acid: A Multistep Synthesis
REAC 750: Cannizzaro Reaction: The Conversion of p-Nitrobenzaldehyde into p-Nitrobenzoic Acid and p-Nitrobenzyl Alcohol
3
19. Substitutions at the
Carbonyl Group
Reactions of Carboxylic
Acids and Derivatives
SYNT 713: Preparing Isopentylacetate by the Fischer Esterification
SYNT 726: Two Methods for the Synthesis of Phenacetin
SYNT 737: Thiamine-Catalyzed Benzoin Condensation
SYNT 743: Converting Benzaldehyde to Benzilic Acid: A Multistep Synthesis
SYNT 745: Synthesizing Aspirin: The Acetylation of Salicylic Acid
SYNT 746: Acetaminophen: The Acetylation of p-Aminophenol
20. Enolate and Other
Carbon Nucleophiles
SYNT 720: The Aldol Condensation: Synthesis of Dibenzalacetone
SYNT 737: Thiamine-Catalyzed Benzoin Condensation
SYNT 754: A Multistep Synthesis Sequence: An Aldol Condensation, a Michael Addition, and Ethylene Ketal Formation
21. The Chemistry of
Radicals
REAC 741: Free Radical Chlorination
SYNT 717: The Diels-Alder Reaction of Anthracene with Maleic Anhydride
22. Carbonyl AlphaSubstitution Reactions SYNT 748: Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence
23. Carbonyl
Condensation
Reactions
24. Synthetic Polymers
25. Carbohydrates
SYNT 720: The Aldol Condensation: Synthesis of Dibenzalacetone
SYNT 737: Thiamine-Catalyzed Benzoin Condensation
SYNT 754: A Multistep Synthesis Sequence: An Aldol Condensation, a Michael Addition, and Ethylene Ketal Formation
SYNT 739: The Synthesis of a Superabsorbent Polymer
SYNT 713: Preparing Isopentylacetate by the Fischer Esterification
4
Recommended Techniques from CER
TECH 700: Practicing Safety in the Organic Chemistry Laboratory
TECH 701: Measuring the Melting Points of Compounds and Mixtures
TECH 702: Using Microscale Techniques
TECH 703: Purifying Acetanilide by Recrystallization
TECH 704: Separating Cyclohexane and Toluene by Distillation
TECH 705: Separating Acids and Neutral Compounds of Solvent Extraction
TECH 706: Separating Camphor from BetaCarotene by Sublimation
TECH 707: Separating a Mixture by Thin-Layer Chromatography
TECH 708: Separating Ferrocene and Acetylferrocene by Adsorption Column Chromatography
TECH 709: Separating and Identifying Mixtures by Gas Chromatography
TECH 710: Identifying an Unknown Compound by Infrared Spectroscopy
TECH 711: Using NMR Spectroscopy to Identify an Unknown Organic Compound
TECH 722: Isolating Clove Oil from Cloves Using Steam Distillation