9780716739210

Modern Projects and Experiments in Organic Chemistry : Miniscale and Williamson Microscale

by ; ; ;
  • ISBN13:

    9780716739210

  • ISBN10:

    0716739216

  • Edition: 2nd
  • Format: Paperback
  • Copyright: 2002-11-08
  • Publisher: W. H. Freeman

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Supplemental Materials

What is included with this book?

Summary

The Manuals Modern Projects and Experiments in Organic Chemistryhelps instructors turn their organic chemistry laboratories into places of discovery and critical thinking. In addition to traditional experiments, the manual offers a variety of inquiry-based experiments and multi-week projects, giving students a better understanding of how lab work is actually accomplished. Instead of simply following directions, students learn how to investigate the experimental process itself. The Program Modern Projects and Experiments in Organic Chemistryis designed to provide the utmost in quality content, student accessibility, and instructor flexibility. The project consists of: 1) A laboratory manual in two versions: miniscale and standard-taper microscale equipment (0-7167-9779-8) miniscale and Williamson microscale equipment (0-7167-3921-6) 2) Custom publishing option.All experiments are available through Freeman's custom publishing service at http://custompub.whfreeman.com. Instructors can use this service to create their own customized lab manual, even including their own material. 3)Techniques in Organic Chemistry. This concise yet comprehensive companion volume provides students with detailed descriptions of important techniques.

Table of Contents

Preface xi
PART 1 EXPERIMENTS
1(236)
Extraction of Caffeine from Tea
3(6)
Purification and Thin-Layer Chromatographic Analysis of Caffeine
9(6)
Optional Experiment: Evaluating TLC Parameters
13(2)
Synthesis of Ethanol by Fermentation of Sucrose
15(4)
Synthesis of Salicylic Acid
19(8)
Analgesics and Synthesis of Aspirin
27(10)
Synthesis of Acetylsalicylic Acid
29(4)
Thin-Layer Chromatographic Analysis of Analgesics
33(4)
Isolation of Essential Oils from Plants
37(10)
(S)-(+)-Carvone from Caraway Seeds
40(4)
Isolation of (R)-(+)-Limonene from Orange Peels
44(3)
Computational Chemistry
47(10)
Radical Halogenation Reactions
57(10)
Radical Chlorination Reactions
59(4)
Optional Experiment: Additional Substrates
62(1)
Optional Computational Chemistry Experiment
62(1)
Photobromination of 1,2-Diphenylethane
63(4)
Nucleophilic Substitution Reactions
67(10)
SN1/SN2 Reactivity of Alkyl Halides
70(2)
Synthesis and Identification of Alkyl Bromides from Unknown Alcohols
72(5)
E2 Elimination of 2-Bromoheptane: Influence of the Base
77(6)
Optional Computational Chemistry Experiment
80(3)
Dehydration of Alcohols
83(10)
Acid-Catalyzed Dehydration of 2-Methyl-2-butanol
86(3)
Optional Experiment: Qualitative Tests for Alkenes
88(1)
Acid-Catalyzed Dehydration of 3-Methylcyclohexanol
89(4)
Optional Experiment: Qualitative Tests for Alkenes
91(2)
Synthesis of Esters from Alcohols
93(14)
Synthesis of Isopentyl Acetate
95(5)
Optional Experiment: Synthesis and Identification of an Ester from an Unknown Alcohol and Acetic Acid
98(2)
Synthesis of Benzocaine
100(3)
Determination of the Equilibrium Constant for an Esterification Reaction
103(4)
Green Chemistry: Oxidation of Cyclohexanol Using Sodium Hypochlorite
107(8)
Oxidation of Cinnamyl Alcohol Using Pyridinium Chlorochromate
115(6)
Grignard Syntheses
121(12)
Synthesis of Phenylmagnesium Bromide for Use as a Synthetic Intermediate
124(3)
Synthesis of 1, 1-Diphenylethanol
127(4)
Synthesis of Benzoic Acid
131(2)
Addition Reactions of Alkenes
133(15)
Free Radical Versus Ionic Addition of Hydrobromic Acid to Alkenes
136(3)
Stereochemistry of Bromine Addition to trans-Cinnamic Acid
139(9)
Synthesis of Polystyrene
148(3)
Optional Experiment: IR Analysis of Commercial Polystyrene Products
148(3)
Phase Transfer Catalysis: Synthesis of Butyl Benzoate
151(6)
Diels-Alder Reaction
157(6)
Selectivity in the Bromination of Acetanilide and 4-Methylacetanilide
163(8)
Optional Computational Chemistry Experiment
169(2)
Acylation of Ferrocene
171(6)
Alkylation of 1,4-Dimethoxybenzene
177(6)
Kinetic Versus Equilibrium Control in the Alkylation of Chlorobenzene
183(8)
Optional Experiments: Role of Nitromethane
189(2)
Reduction Reactions of 3-Nitroacetophenone
191(6)
Reduction of 3-Nitroacetophenone Using Sodium Borohydride
193(2)
Reduction of 3-Nitroacetophenone Using Tin and Hydrochloric Acid
195(2)
Horner-Emmons-Wittig Synthesis of Methyl E-4-methoxycinnamate
197(6)
Synthesis of Triphenylmethane Dyes: Crystal Violet and Malachite Green
203(8)
Enolate Chemistry: Synthesis of trans-1,2-Dibenzoylcyclopropane
211(6)
Amide Chemistry
217(20)
Synthesis of Benzoylamino Acids from Glycine, Alanine, and Valine
222(5)
Optional Experiment: Benzoylamino Acids from L-Alanine and L-Valine
226(1)
Synthesis of a Mosquito Repellant: N,N-Diethylmeta-toluamide (DEET)
227(10)
PART 2 PROJECTS
237(156)
Identification of a White Solid: A Team Approach
239(4)
Optional Experiment: IR or NMR Spectroscopy
241(2)
Using Extraction to Separate a Mixture
243(4)
Separation and Purification of the Compounds in the Unknown Mixture
244(1)
Melting Points, Purity, and Identification of the Compounds in the Mixture
245(2)
Hydrolysis of an Unknown Ester
247(12)
Hydrolysis and Azeotropic Distillation
250(2)
Recrystallization and Extraction
252(2)
Distillation, Boiling Points, and Melting Points
254(1)
Identification of the Unknown Ester
255(4)
Interconversion of 4-tert-Butylcyclohexanol and 4-tert-Butylcyclohexanone
259(14)
Green Chemistry: Sodium Hypochlorite Oxidation of 4-tert-Butylcyclohexanol
264(3)
Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone
267(5)
Computational Chemistry Experiment
272(1)
Synthesis of 1-Bromobutane and the Grignard Synthesis of an Alcohol
273(12)
Synthesis of 1-Bromobutane from 1-Butanol
276(3)
Optional Syntheses of Alkyl Halides
279(1)
Grignard Synthesis of Secondary and Tertiary Alcohols
279(6)
E1/E2 Elimination Reactions
285(10)
Acid-Catalyzed Dehydration of 2-Methyl-2-butanol
289(1)
Synthesis of 2-Chloro-2-methylbutane
290(1)
Base-Catalyzed Dehydrochlorination of 2-Chloro-2-methylbutane
291(4)
Synthesis and Hydroboration-Oxidation of 1-Phenylcyclohexene
295(14)
Grignard Synthesis of 1-Phenylcyclohexanol
301(2)
Acid-Catalyzed Dehydration of 1-Phenylcyclohexanol
303(2)
Hydroboration-Oxidation of 1-Phenylcyclohexene
305(2)
Computational Chemistry Experiment
307(2)
Electrophilic Aromatic Substitution: The Diacetylation of Ferrocene
309(14)
Synthesis of Diacetylferrocene
313(3)
Purification by Column Chromatography
316(2)
Optional Column Chromatography for Isolation of the Minor Diacetylferrocene Isomer
318(5)
Stereochemistry of Electrophilic Addition to an Alkene
323(12)
Synthesis of Cyclohex-4-ene-cis-1,2-dicarboxylic Acid
329(2)
Bromination of Cyclohex-4-ene-cis-1,2-dicarboxylic Acid
331(1)
Synthesis of Dimethyl 4,5-Dibromocyclohexane-cis-1,2-dicarboxylate
332(3)
Diels-Alder Cycloadditions of Dienophiles to 2,3-Dimethyl-1,3-butadiene
335(16)
Competition Reactions of 2,3-Dimethyl-1,3-butadiene and 1,3-Cyclohexadiene with Maleic Anhydride
341(3)
Competition Reactions of 2,3-Dimethyl-1,3-butadiene with Diethyl trans-2-Butenedioate and Diethyl cis-2-Butenedioate
344(2)
Competition Reactions of 2,3-Dimethyl-1,3-butadiene with Dimethyl cis-2-Butenedioate and Dimethyl 2-Butynedioate
346(2)
Designing and Carrying Out a Synthesis of Dimethyl 4,5-Dimethylbenzene-1,2-dicarboxylate by Diels-Alder and Dehydrogenation Chemistry
348(3)
Aldol-Dehydration Chemistry Using Unknown Aldehydes and Ketones
351(10)
Preparation and Characterization of the Aldol-Dehydration Condensation Product
355(2)
Preparation and Characterization of Solid Derivaties of the Unknown Aldehyde and Ketone
357(4)
Biochemical Catalysis and the Stereochemistry of Borohydride Reduction
361(12)
Thiamine-Catalyzed Benzoin Condensation
367(1)
Stereoselectivity of the Borohydride Reduction of Benzoin
368(5)
Designing a Multistep Synthesis
373(4)
Sugars: Glucose Pentaacetates
377(10)
Synthesis of α-D-Glucose Pentaacetate and β-D-Glucose Pentaacetate
381(2)
Investigation of Kinetic and Equilibrium Control in the Glucose Pentaacetate System
383(2)
Computational Chemistry Experiment
385(2)
Enantioselective Synthesis by Enzymatic Hydrolysis Using Pig-Liver Esterase
387(6)
Synthesis of Dimethyl Cyclohex-4-ene-cis-1,2-dicarboxylate by Diels-Alder Cycloaddition and Esterification
390(2)
Synthesis of (±)-Methyl Hydrogen Cyclohex-4-ene-cis-1,2-dicarboxylate
392(1)
Enantioselective Enzymatic Hydrolysis of Dimethyl Cyclohex-4-ene-cis-1,2-dicarboxylate
393

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