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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