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.
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Chapter Title
2. Polar Covalent
Bonds; Acids and
Bases
4. Stereochemistry
of Alkanes and
Cycloalkanes
Recommended Experiment(s) from CER
ANAL 735: Catalytic Hydrogenation of Unknowns
SYNT 719: Brominating Alkenes
REAC 734: Molecular Rearrangement Reactions: Azobenzene and Benzilic Acid
ANAL 735: Catalytic Hydrogenation of Unknowns
2
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
Reactivity
SYNT 719: Brominating Alkenes
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
Organic
Synthesis
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
3
9. Stereochemistry
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
10. Alkyl Halides
11. Reactions of
Alkyl Halides:
Nucleophilic
Substitutions and
Eliminations
14. Conjugated
Dienes and
Ultraviolet
Spectroscopy
16. Chemistry of
Benzene:
Electrophilic
Aromatic
Substitution.
A Brief Review of
Organic Reactions
SYNT 738: Copper-Catalyzed Oxidation of Benzoin to Benzil
SYNT 719: Brominating Alkenes
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
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
4
SYNT 713: Preparing Isopentylacetate by the Fischer Esterification
REAC 721: Synthesis of Trans-9-(2-Phenylethenyl)Anthracene: A Wittig Reaction
19. Aldehydes and
Ketones:
Nucleophilic
Addition
Reactions
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
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
AlphaSubstitution
Reactions
REAC 715: Reducing Benzil Using Sodium Borohydride
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
25. Biomolecules:
Carbohydrates
SYNT 754: A Multistep Synthesis Sequence: An Aldol Condensation, a Michael Addition, and Ethylene Ketal Formation
SYNT 713: Preparing Isopentylacetate by the Fischer Esterification
5
30. Orbitals and
Organic
Chemistry:
Pericyclic
Reactions
31. Synthetic
Polymers
SYNT 717: The Diels-Alder Reaction of Anthracene with Maleic Anhydride
SYNT 748: Formation of Benzyne and Its Diels-Alder Reaction: A Multistep Reaction Sequence
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