Whitten, Davis, and Peck, General Chemistry, 6th Edition
|[pic] |Recommended CER Experiments |
| |to accompany |
| |McMurry, Organic Chemistry, Sixth 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 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 |Recommended Experiment(s) from CER |
|2. Polar Covalent Bonds; Acids and |ANAL 735: Catalytic Hydrogenation of Unknowns |
|Bases | |
|4. Stereochemistry of Alkanes and |SYNT 719: Brominating Alkenes |
|Cycloalkanes |REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid |
| |ANAL 735: Catalytic Hydrogenation of Unknowns |
| |SYNT 713: Preparing Isopentylacetate by the Fischer Esterification |
| |REAC 714: Studying SN1 and SN2 Reactions: Nucleophilic Substitution |
| |SYNT 719: Brominating Alkenes |
| |SYNT 725: Oxidizing Methoxybenzyl Alcohol to Methoxybenzaldehyde Using Phase Transfer Catalysis |
| |KINE 733: The Kinetics of Solvolysis of 2-Chloro-2-Methylpropane |
|5. An Overview of Organic Reactions|REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid |
| |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 |
| |ANAL 751: Enantiomeric Purity of Commercial Ibuprofen |
| |TECH 752: Resolving a Racemic Mixture: Using (-)-Proline to Separate (±)-Phenylsuccinic Acid |
|6. Alkenes: Structure and |SYNT 719: Brominating Alkenes |
|Reactivity | |
| |REAC 712: Dehydrating Cyclohexanol |
| |SYNT 719: Brominating Alkenes |
|7. Alkenes: Reactions and Synthesis|REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid |
| |REAC 736: The Pinacol Rearrangement |
| |REAC 741: Free Radical Chlorination |
| |ANAL 751: Enantiomeric Purity of Commercial Ibuprofen |
| |TECH 752: Resolving a Racemic Mixture: Using (-)-Proline to Separate (±)-Phenylsuccinic Acid |
|8. Alkynes: An Introduction to |SYNT 719: Brominating Alkenes |
|Organic Synthesis |REAC 742: Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol |
| |REAC 747: Hydroboration and Oxidation of 1Hexene to Make 1Hexanol |
| |SYNT 719: Brominating Alkenes |
|9. Stereochemistry |REAC 742: Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol |
| |REAC 747: Hydroboration and Oxidation of 1Hexene to Make 1Hexanol |
|10. Alkyl Halides |SYNT 738: Copper-Catalyzed Oxidation of Benzoin to Benzil |
|11. Reactions of Alkyl Halides: |SYNT 719: Brominating Alkenes |
|Nucleophilic Substitutions and | |
|Eliminations | |
|14. Conjugated Dienes and |SYNT 719: Brominating Alkenes |
|Ultraviolet Spectroscopy |REAC 742: Acid-Catalyzed Hydration of 1-Hexene to Make 2-Hexanol |
| |REAC 747: Hydroboration and Oxidation of 1Hexene to Make 1Hexanol |
|16. Chemistry of Benzene: |REAC 716: Nitrating Acetanilide or Methyl Benzoate: Electrophilic Aromatic Substitution |
|Electrophilic Aromatic |SYNT 723: Friedel-Crafts Acylation: Synthesis of 4-Methoxyacetophenone |
|Substitution. |SYNT 724: Friedel-Crafts Alkylation: Kinetic versus Thermodynamic Control |
|A Brief Review of Organic Reactions|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 |
| |SYNT 713: Preparing Isopentylacetate by the Fischer Esterification |
| |REAC 721: Synthesis of Trans-9-(2-Phenylethenyl)Anthracene: A Wittig Reaction |
|19. Aldehydes and Ketones: |SYNT 726: Two Methods for the Synthesis of Phenacetin |
|Nucleophilic Addition Reactions |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 |
| |REAC 750: Cannizaro Reaction: The Conversion of p-Nitrobenzaldehyde into p-Nitrobenzoic Acid and p-Nitrobenzyl Alcohol |
| |SYNT 717: The Diels-Alder Reaction of Anthracene with Maleic Anhydride |
|20. Carboxylic Acids and Nitriles |SYNT 720: The Aldol Condensation: Synthesis of Dibenzalacetone |
| |SYNT 737: Thiamine-Catalyzed Benzoin Condensation |
| |SYNT 748: Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence |
| |SYNT 754: A Multistep Synthesis Sequence: An Aldol Condensation, a Michael Addition, and Ethylene Ketal Formation |
|22. Carbonyl Alpha-Substitution |REAC 715: Reducing Benzil Using Sodium Borohydride |
|Reactions |SYNT 718: Nucleophilic Addition to Carbonyl: Grignard Reaction with an Aldehyde |
|23. Carbonyl Condensation Reactions|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 |
|25. Biomolecules: |SYNT 713: Preparing Isopentylacetate by the Fischer Esterification |
|Carbohydrates | |
|30. Orbitals and Organic Chemistry:|SYNT 717: The Diels-Alder Reaction of Anthracene with Maleic Anhydride |
|Pericyclic Reactions |SYNT 748: Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence |
|31. Synthetic Polymers |SYNT 739: The Synthesis of a Superabsorbent Polymer |
|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 Beta-Carotene 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 |
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