Chem 227: Assignments / Activities
Reading/Homework * Worksheets * Lab Schedule * Experiments * Lab Techniques & Videos

Reading / Homework:

Key textbook & class topics are below and emphasized in Bold Red. Webassign, Worksheet, and ACS problems will serve as examples for many of the types of questions that will be on exams and quizzes.

(In-chapter textbook problems are also important and relate to pre-class preparation and i-clicker in-class questions. Attempting end of chapter problems is encouraged as your time allows.)

Webassign Homework . All assignments are to be done individually. Due dates are embedded on line and these homework problems should be your main focus along with the collaborative/group Worksheets.



ORGANIC CHEMISTRY (Carey 7th ed)

CHAPTER 11
Arenes and Aromaticity 420
11.1 Benzene 421
11.2 Kekulé and the Structure of Benzene 422
11.3 A Resonance Picture of Bonding in Benzene 424
11.4 The Stability of Benzene 424
11.5 An Orbital Hybridization View of Bonding in Benzene 426
11.6 The Pi Molecular Orbitals of Benzene 427
11.7 Substituted Derivatives of Benzene and Their Nomenclature 428
11.8 Polycyclic Aromatic Hydrocarbons 430
11.9 Physical Properties of Arenes 431
Carbon Clusters, Fullerenes, and Nanotubes 432

11.10 Reactions of Arenes: A Preview 432
11.11 The Birch Reduction 433
11.12 Free-Radical Halogenation of Alkylbenzenes 436
11.13 Oxidation of Alkylbenzenes 438
11.14 Sn1 Reactions of Benzylic Halides 440
11.15 Sn2 Reactions of Benzylic Halides 441
11.16 Preparation of Alkenylbenzenes 442
11.17 Addition Reactions of Alkenylbenzenes 443
11.18 Polymerization of Styrene 445
11.19 Cyclobutadiene and Cyclooctatetraene 446
11.20 Hückel’s Rule 448
11.21 Annulenes 450
11.22 Aromatic Ions 452
11.23 Heterocyclic Aromatic Compounds 455
11.24 Heterocyclic Aromatic Compounds and Hückel’s Rule 457
11.25 Summary 459

Problems 462
Descriptive Passage and Interpretive Problems 11: The Hammett Equation 466

CHAPTER 12
Reactions of Arenes: Electrophilic Aromatic Substitution 470
12.1 Representative Electrophilic Aromatic Substitution Reactions of Benzene 471
12.2 Mechanistic Principles of Electrophilic Aromatic Substitution 472
12.3 Nitration of Benzene 474
12.4 Sulfonation of Benzene 476
12.5 Halogenation of Benzene 477
12.6 Friedel–Crafts Alkylation of Benzene 478
12.7 Friedel–Crafts Acylation of Benzene 481
12.8 Synthesis of Alkylbenzenes by Acylation–Reduction 483
12.9 Rate and Regioselectivity in Electrophilic Aromatic Substitution 484
12.10 Rate and Regioselectivity in the Nitration of Toluene 485
12.11 Rate and Regioselectivity in the Nitration of (Trifluoromethyl)benzene 488
12.12 Substituent Effects in Electrophilic Aromatic Substitution: Activating Substituents 490
12.13 Substituent Effects in Electrophilic Aromatic Substitution: Strongly Deactivating Substituents 493
12.14 Substituent Effects in Electrophilic Aromatic Substitution: Halogens 496
12.15 Multiple Substituent Effects 498
12.16 Regioselective Synthesis of Disubstituted Aromatic Compounds 499
12.17 Substitution in Naphthalene 502
12.18 Substitution in Heterocyclic Aromatic Compounds 502
12.19 Summary 504

Problems 507
Descriptive Passage and Interpretive Problems 12: Nucleophilic Aromatic Substitution 512

CHAPTER 13
Spectroscopy 516
13.1 Principles of Molecular Spectroscopy: Electromagnetic Radiation 518
13.2 Principles of Molecular Spectroscopy: Quantized Energy States 519
13.3 Introduction to 1 H NMR Spectroscopy 519
13.4 Nuclear Shielding and 1 H Chemical Shifts 521
13.5 Effects of Molecular Structure on 1 H Chemical Shifts 524
Ring Currents: Aromatic and Antiaromatic 529
13.6 Interpreting 1 H NMR Spectra 530
13.7 Spin–Spin Splitting in 1 H NMR Spectroscopy 532
13.8 Splitting Patterns: The Ethyl Group 534
13.9 Splitting Patterns: The Isopropyl Group 536
13.10 Splitting Patterns: Pairs of Doublets 536
13.11 Complex Splitting Patterns 538
13.12 1 H NMR Spectra of Alcohols 539
Magnetic Resonance Imaging (MRI) 540
13.13 NMR and Conformations 540
13.14 13 C NMR Spectroscopy 541
13.15 13 C Chemical Shifts 543
13.16 13 C NMR and Peak Intensities 545
13.17 13 C 1 H Coupling 546
13.18 Using DEPT to Count Hydrogens Attached to 13 C 546
13.19 2D NMR: COSY and HETCOR 547
13.20 Introduction to Infrared Spectroscopy 550
Spectra by the Thousands 551
13.21 Infrared Spectra 552
13.22 Characteristic Absorption Frequencies 554
13.23 Ultraviolet-Visible (UV-VIS) Spectroscopy 557
13.24 Mass Spectrometry 559
13.25 Molecular Formula as a Clue to Structure 563
Gas Chromatography, GC/MS, and MS/MS 564
13.26 Summary 566

Problems 569
Descriptive Passage and Interpretive Problems 13: Calculating Aromatic 13 C Chemical Shifts 575

CHAPTER 16
Ethers, Epoxides, and Sulfides 662
16.1 Nomenclature of Ethers, Epoxides, and Sulfides 663
16.2 Structure and Bonding in Ethers and Epoxides 664
16.3 Physical Properties of Ethers 665
16.4 Crown Ethers 667
16.5 Preparation of Ethers 668
Polyether Antibiotics 669
16.6 The Williamson Ether Synthesis 670
16.7 Reactions of Ethers: A Review and a Preview 671
16.8 Acid-Catalyzed Cleavage of Ethers 672
16.9 Preparation of Epoxides: A Review and a Preview 674
16.10 Conversion of Vicinal Halohydrins to Epoxides 675
16.11 Reactions of Epoxides: A Review and a Preview 676
16.12 Nucleophilic Ring Opening of Epoxides 677
16.13 Acid-Catalyzed Ring Opening of Epoxides 679

16.14 Epoxides in Biological Processes 682
16.15 Preparation of Sulfides 682
16.16 Oxidation of Sulfides: Sulfoxides and Sulfones 683
16.17 Alkylation of Sulfides: Sulfonium Salts 684
16.18 Spectroscopic Analysis of Ethers, Epoxides, and Sulfides 685
16.19 Summary 688
Problems 692
Descriptive Passage and Interpretive Problems 16: Epoxide Rearrangements and the NIH Shift 697

CHAPTER 17
Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group 700
17.1 Nomenclature 701
17.2 Structure and Bonding: The Carbonyl Group 704
17.3 Physical Properties 706
17.4 Sources of Aldehydes and Ketones 707
17.5 Reactions of Aldehydes and Ketones: A Review and a Preview 710
17.6 Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones 711
17.7 Cyanohydrin Formation 715
17.8 Acetal Formation 718
17.9 Acetals as Protecting Groups 721
17.10 Reaction with Primary Amines: Imines 722
Imines in Biological Chemistry 725
17.11 Reaction with Secondary Amines: Enamines 727
17.12 The Wittig Reaction 728
17.13 Planning an Alkene Synthesis via the Wittig Reaction 730
17.14 Stereoselective Addition to Carbonyl Groups 732
17.15 Oxidation of Aldehydes 733
17.16 Baeyer–Villiger Oxidation of Ketones 734
17.17 Spectroscopic Analysis of Aldehydes and Ketones 736
17.18 Summary 738

Problems 742
Descriptvie Passage and Interpretive Problems 17: Alcohols, Aldehydes, and Carbohydrates 749

CHAPTER 18
Enols and Enolates 752
18.1 The -Hydrogen and Its pKa 753
18.2 The Aldol Condensation 757
18.3 Mixed Aldol Condensations 761
18.4 Alkylation of Enolate Ions 763
18.5 Enolization and Enol Content 764
18.6 Stabilized Enols 766
18.7 Halogenation of Aldehydes and Ketones 768
18.8 Mechanism of Halogenation of Aldehydes and Ketones 768
18.9 The Haloform Reaction 770
18.10 Some Chemical and Stereochemical Consequences of Enolization 772
The Haloform Reaction and the Biosynthesis of Trihalomethanes 773
18.11 Effects of Conjugation in ,-Unsaturated Aldehydes and Ketones 774
18.12 Conjugate Addition to ,-Unsaturated Carbonyl Compounds 775
18.13 Addition of Carbanions to ,-Unsaturated Ketones: The Michael Reaction 778
18.14 Conjugate Addition of Organocopper Reagents to ,-Unsaturated Carbonyl Compounds 778
18.15 Summary 779

Problems 782
Descriptive Passage and Interpretive Problems 18: Enolate Regiochemistry and Stereochemistry 787

CHAPTER 19
Carboxylic Acids 790
19.1 Carboxylic Acid Nomenclature 791
19.2 Structure and Bonding 793
19.3 Physical Properties 794
19.4 Acidity of Carboxylic Acids 794
19.5 Salts of Carboxylic Acids 797
19.6 Substituents and Acid Strength 799
19.7 Ionization of Substituted Benzoic Acids 801
19.8 Dicarboxylic Acids 802
19.9 Carbonic Acid 802
19.10 Sources of Carboxylic Acids 803
19.11 Synthesis of Carboxylic Acids by the Carboxylation of Grignard Reagents 806
19.12 Synthesis of Carboxylic Acids by the Preparation and Hydrolysis of Nitriles 806
19.13 Reactions of Carboxylic Acids: A Review and a Preview 807
19.14 Mechanism of Acid-Catalyzed Esterification 808
19.15 Intramolecular Ester Formation: Lactones 811
19.16 Alpha Halogenation of Carboxylic Acids: The Hell–Volhard–Zelinsky Reaction 813
19.17 Decarboxylation of Malonic Acid and Related Compounds 815
19.18 Spectroscopic Analysis of Carboxylic Acids 817
19.19 Summary 818

Problems 821
Descriptive Passage and Interpretive Problems 19: Lactonization Methods 825

CHAPTER 20
Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution 825
20.1 Nomenclature of Carboxylic Acid Derivatives 830
20.2 Structure and Reactivity of Carboxylic Acid Derivatives 831
20.3 General Mechanism for Nucleophilic Acyl Substitution 834
20.4 Nucleophilic Acyl Substitution in Acyl Chlorides 836
20.5 Nucleophilic Acyl Substitution in Carboxylic Acid Anhydrides 839
20.6 Sources of Esters 842
20.7 Physical Properties of Esters 842
20.8 Reactions of Esters: A Review and a Preview 844
20.9 Acid-Catalyzed Ester Hydrolysis 844
20.10 Ester Hydrolysis in Base: Saponification 848
20.11 Reaction of Esters with Ammonia and Amines 851
20.12 Amides 852
20.13 Hydrolysis of Amides 857
20.14 Lactams 861
-Lactam Antibiotics 861
20.15 Preparation of Nitriles 862
20.16 Hydrolysis of Nitriles 863
20.17 Addition of Grignard Reagents to Nitriles 864
20.18 Spectroscopic Analysis of Carboxylic Acid Derivatives 866
20.19 Summary 867

Problems 870
Descriptive Passage and Interpretive Problems 20: Thioesters 876

CHAPTER 21
Ester Enolates 880
21.1 Ester Hydrogens and Their pKa ’s 881
21.2 The Claisen Condensation 883
21.3 Intramolecular Claisen Condensation: The Dieckmann Reaction 886
21.4 Mixed Claisen Condensations 886
21.5 Acylation of Ketones with Esters 887
21.6 Ketone Synthesis via -Keto Esters 888
21.7 The Acetoacetic Ester Synthesis 889
21.8 The Malonic Ester Synthesis 892
21.9 Michael Additions of Stabilized Anions 894
21.10 Reactions of LDA-Generated Ester Enolates 895
21.11 Summary 897

Problems 899
Descriptive Passage and Interpretive Problems 21: The Enolate Chemistry of Dianions 903

CHAPTER 22
Amines 908
22.1 Amine Nomenclature 909
22.2 Structure and Bonding 911
22.3 Physical Properties 913
22.4 Basicity of Amines 914
Amines as Natural Products 919
22.5 Tetraalkylammonium Salts as Phase-Transfer Catalysts 921
22.6 Reactions That Lead to Amines: A Review and a Preview 922
22.7 Preparation of Amines by Alkylation of Ammonia 923
22.8 The Gabriel Synthesis of Primary Alkylamines 924
22.9 Preparation of Amines by Reduction 926
22.10 Reductive Amination 928
22.11 Reactions of Amines: A Review and a Preview 929
22.12 Reaction of Amines with Alkyl Halides 931
22.13 The Hofmann Elimination 931
22.14 Electrophilic Aromatic Substitution in Arylamines 932
22.15 Nitrosation of Alkylamines 935
22.16 Nitrosation of Arylamines 937
22.17 Synthetic Transformations of Aryl Diazonium Salts 938
22.18 Azo Coupling 942
From Dyes to Sulfa Drugs 943
22.19 Spectroscopic Analysis of Amines 944
22.20 Summary 947

Problems 953
Descriptive Passage and Interpretive Problems 22: Synthetic Applications of Enamines 960

CHAPTER 23
Aryl Halides 964
23.1 Bonding in Aryl Halides 965
23.2 Sources of Aryl Halides 966
23.3 Physical Properties of Aryl Halides 966
23.4 Reactions of Aryl Halides: A Review and a Preview 966
23.5 Nucleophilic Substitution in Nitro-Substituted Aryl Halides 968
23.6 The Addition–Elimination Mechanism of Nucleophilic Aromatic Substitution 971
23.7 Related Nucleophilic Aromatic Substitution Reactions 973
23.8 The Elimination–Addition Mechanism of Nucleophilic Aromatic Substitution: Benzyne 974
23.9 Diels–Alder Reactions of Benzyne 978
23.10 m-Benzyne and p-Benzyne 979

23.11 Summary 980
Problems 982
Descriptive Passage and Interpretive Problems 23: The Heck Reaction 986

CHAPTER 24
Phenols 990
24.1 Nomenclature 991
24.2 Structure and Bonding 992
24.3 Physical Properties 993
24.4 Acidity of Phenols 994
24.5 Substituent Effects on the Acidity of Phenols 995
24.6 Sources of Phenols 996
24.7 Naturally Occurring Phenols 998
24.8 Reactions of Phenols: Electrophilic Aromatic Substitution 999
24.9 Acylation of Phenols 1001
24.10 Carboxylation of Phenols: Aspirin and the Kolbe–Schmitt Reaction 1002
24.11 Preparation of Aryl Ethers 1004
Agent Orange and Dioxin 1005
24.12 Cleavage of Aryl Ethers by Hydrogen Halides 1006
24.13 Claisen Rearrangement of Allyl Aryl Ethers 1006
24.14 Oxidation of Phenols: Quinones 1007
24.15 Spectroscopic Analysis of Phenols 1009

24.16 Summary 1010
Problems 1013
Descriptive Passage and Interpretive Problems 24: Directed Metalation of Aryl Ethers 1018

CHAPTER 25
Carbohydrates 1022
25.1 Classification of Carbohydrates 1023
25.2 Fischer Projections and D–L Notation 1024
25.3 The Aldotetroses 1025
25.4 Aldopentoses and Aldohexoses 1026
25.5 A Mnemonic for Carbohydrate Configurations 1028
25.6 Cyclic Forms of Carbohydrates: Furanose Forms 1029
25.7 Cyclic forms of Carbohydrates: Pyranose Forms 1032
25.8 Mutarotation and the Anomeric Effect 1035
25.9 Ketoses 1037
25.10 Deoxy Sugars 1038
25.11 Amino Sugars 1039
25.12 Branched-Chain Carbohydrates 1040
25.13 Glycosides 1040
25.14 Disaccharides 1042
25.15 Polysaccharides 1044

How Sweet It Is! 1045
25.16 Reactions of Carbohydrates 1047
25.17 Reduction of Monosaccharides 1047
25.18 Oxidation of Monosaccharides 1047
25.19 Cyanohydrin Formation and Chain Extension 1049
25.20 Epimerization, Isomerization, and Retro-Aldol Cleavage 1050
25.21 Acylation and Alkylation of Hydroxyl Groups 1052
25.22 Periodic Acid Oxidation 1053

25.23 Summary 1054
Problems 1057
Descriptive Passage and Interpretive Problems 25: Emil Fischer and the Structure of (+)-Glucose 1061

CHAPTER 26
Lipids 1064
26.1 Acetyl Coenzyme A 1066
26.2 Fats, Oils, and Fatty Acids 1067
26.3 Fatty Acid Biosynthesis 1070
26.4 Phospholipids 1073
26.5 Waxes 1075
26.6 Prostaglandins 1076

Nonsteroidal Antiinflammatory Drugs (NSAIDS) and COX-2 Inhibitors 1078
26.7 Terpenes: The Isoprene Rule 1079
26.8 Isopentenyl Pyrophosphate: The Biological Isoprene Unit 1082
26.9 Carbon–Carbon Bond Formation in Terpene Biosynthesis 1082
26.10 The Pathway from Acetate to Isopentenyl Diphosphate 1086
26.11 Steroids: Cholesterol 1087
26.12 Vitamin D 1090

Good Cholesterol? Bad Cholesterol? What’s the Difference? 1091
26.13 Bile Acids 1092
26.14 Corticosteroids 1092
26.15 Sex Hormones 1093
26.16 Carotenoids 1093
Anabolic Steroids 1094

Crocuses Make Saffron from Carotenes 1095
26.17 Summary 1096
Problems 1098
Descriptive Passage and Interpretive Problems 26: Polyketides 1101

CHAPTER 27
Amino Acids, Peptides, and Proteins 1106
27.1 Classification of Amino Acids 1108
27.2 Stereochemistry of Amino Acids 1113
27.3 Acid–Base Behavior of Amino Acids 1114

27.4 Synthesis of Amino Acids 1117
Electrophoresis 1117
27.5 Reactions of Amino Acids 1119
27.6 Some Biochemical Reactions of Amino Acids 1120
27.7 Peptides 1127
27.8 Introduction to Peptide Structure Determination 1130
27.9 Amino Acid Analysis 1130
27.10 Partial Hydrolysis of Peptides 1131
27.11 End Group Analysis 1132
27.12 Insulin 1133
27.13 The Edman Degradation and Automated Sequencing of Peptides 1134
Peptide Mapping and MALDI Mass Spectrometry 1136
27.14 The Strategy of Peptide Synthesis 1137
27.15 Amino Group Protection 1138
27.16 Carboxyl Group Protection 1140
27.17 Peptide Bond Formation 1141
27.18 Solid-Phase Peptide Synthesis: The Merrifield Method 1143
27.19 Secondary Structures of Peptides and Proteins 1145
27.20 Tertiary Structure of Polypeptides and Proteins 1148

27.21 Coenzymes 1152
Oh NO! It’s Inorganic! 1153
27.22 Protein Quaternary Structure: Hemoglobin 1153
27.23 Summary 1154
Problems 1156
Descriptive Passage and Interpretive Problems 27: Amino Acids in Enantioselective Synthesis 1159

CHAPTER 28
Nucleosides, Nucleotides, and Nucleic Acids 1162
28.1 Pyrimidines and Purines 1163
28.2 Nucleosides 1166
28.3 Nucleotides 1167

28.4 Bioenergetics 1170
28.5 ATP and Bioenergetics 1170
28.6 Phosphodiesters, Oligonucleotides, and Polynucleotides 1172
28.7 Nucleic Acids 1173
28.8 Secondary Structure of DNA: The Double Helix 1174
“It Has Not Escaped Our Notice . . .” 1175
28.9 Tertiary Structure of DNA: Supercoils 1177
28.10 Replication of DNA 1178
28.11 Ribonucleic Acids 1180
28.12 Protein Biosynthesis 1183

RNA World 1184
28.13 AIDS 1184
28.14 DNA Sequencing 1185
28.15 The Human Genome Project 1187
28.16 DNA Profiling and the Polymerase Chain Reaction 1188
28.17 Summary 1191
Problems 1194
Descriptive Passage and Interpretive Problems 28: Oligonucleotide Synthesis 1195

CHAPTER 29
Synthetic Polymers 1200
29.1 Some Background 1201
29.2 Polymer Nomenclature 1202
29.3 Classification of Polymers: Reaction Type 1203

29.4 Classification of Polymers: Chain-Growth and Step-Growth 1204
29.5 Classification of Polymers: Structure 1205
29.6 Classification of Polymers: Properties 1207
29.7 Addition Polymers: A Review and a Preview 1209
29.8 Chain Branching in Free-Radical Polymerization 1211
29.9 Anionic Polymerization: Living Polymers 1214
29.10 Cationic Polymerization 1216
29.11 Polyamides 1217
29.12 Polyesters 1218
29.13 Polycarbonates 1219
29.14 Polyurethanes 1220
29.15 Copolymers 1221
29.16 Summary 1223
Problems 1225
Descriptive Passage and Interpretive Problems 29: Chemical Modification of Polymers 1227


 

IR (Infrared) / UV Spectrosopy & Mass Spectrometry

IR (Infrared) / UV Spectrosopy & Mass Spectrometry (MS) Lab Worksheet .pdf

1H NMR Spectrosopy

1H NMR Spectrosopy: Interpretation / Prediction & Reactions Lab Worksheet .pdf

13C NMR Spectrosopy

13C NMR Spectrosopy: Interpretation / Prediction & Reactions Lab Worksheet .pdf

Activity 4 Draft Publication (Exercise/Worksheet)
Activity 5 (Worksheet) - Aromaticity .pdf
Activity 6 (Worksheet) - Electrophilic Aromatic Substitution .pdf.
Activity 7 (Worksheet) - 1H & 13C NMRs / Electrophilic Aromatic Substitution Worksheet .pdf
Activity 8 (Worksheet) - Carboxylic Acid Derivatives
Activity 9 (Worksheet) - Aldehydes & Ketones/ Nu. Subs.
Activity 10 (Worksheet) - Aldehydes & Ketones/ Enolates
Activity 11 (Worksheet) - Enolates: Synthesis and Reactions of b-Dicarbonyl Compounds
Activity 12: Aldehyde-Ketone Synthesis (Aldrich)
 
Exercise/Worksheet - Carbohydrates
Amines Worksheet

Library Research / Calibrated Peer Review (CPR)

LABORATORY


Worksheets:

NOTE: Worksheets are in pdf format. You will need Adobe Acrobat Reader to view and print them which can be downloaded for free at: http://www.adobe.com/products/acrobat/readstep2.html

IR (Infrared) / UV Spectrosopy & Mass Spectrometry
IR (Infrared) / UV Spectrosopy & Mass Spectrometry (MS) Lab Worksheet .pdf

1H NMR Spectrosopy
1H NMR Spectrosopy: Interpretation / Prediction & Reactions Lab Worksheet .pdf

13C NMR Spectrosopy
13C NMR Spectrosopy: Interpretation / Prediction & Reactions Lab Worksheet .pdf

Aromaticity .pdf

Electrophilic Aromatic Substitution .pdf

1H & 13C NMRs / Electrophilic Aromatic Substitution Worksheet .pdf

Aldehydes & Ketones: Synthesis and Nucleophilic Addition .pdf

Aldehyde & Ketone Syntheses .pdf

Synthesis and Reactions of Dicarbonyl Compounds .pdf

Carboxylic Acids .pdf

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitutions .pdf

Exploration 3-form .pdf

Nucleophilic Aromatic Substitution .pdf

Amines .pdf

Carbohydrates .pdf

Halides-Tosylates I .pdf
Halides-Tosylates II .pdf
Halides-Tosylates Synthesis .pdf

Molecular Modeling / Resonance .pdf

Review .pdf


Laboratory

  1. ORGANIC COMPOUNDS: Preparation / Isolation / Purification / Identification;
  2. SAFETY: General Regulations & Lab Guidelines
  3. LABORATORY EQUIPMENT: Aldrich-Kit with Ground Glass Joints
  4. LABORATORY SKILLS: Organic Lab Skills & Operations Check List
  5. RECORD KEEPING: Research Notebooks & Reports

NOTE: Check List must be completed as part of the pre-lab before you may start any lab experiment. You should be able to describe each skill that is to be used in the lab to Dr. R.. Upon completion of the lab experiment you should be able to demonstrate and to teach someone the skills that you acquired.

Tentative Lab Schedule: (Refer to the course calendar for more exact details and for Due dates.)
WEEK
DATES
Activity
Experiments
1

Jan 25-29

 

Lab Drawer / Equipment Check Out
Aldrich-Kit with Ground Glass Joints

Lab Skills & Operations Check List
2
Feb 1-5

1H & 13C NMRs
Operation & Unknown Identification

Peer Review Analysis
Integrated Spectroscopy and Reaction Chemistry: Analysis of a Draft for Publication - pdf
----- Spectra - pdf
----- Team Form - pdf

3

Feb 8-12

 

Synthesis Project: Electrophilic Aromatic Substitution Reactions/ Acylation
Project Instructions .pdf
Electrophilic Aromatic Substitution Worksheet .pdf
1H & 13C NMRs / Electrophilic Aromatic Substitution Worksheet .pdf

 

4

Feb 15

-19

Synthesis Project: Electrophilic Aromatic Substitution Reactions/ Acylation
Project Instructions .pdf
Electrophilic Aromatic Substitution Worksheet .pdf
1H & 13C NMRs / Electrophilic Aromatic Substitution Worksheet .pdf

Acylation

5
Feb 22-26

Synthesis Project: Electrophilic Aromatic Substitution Reactions/ Acylation
Project Instructions .pdf
Electrophilic Aromatic Substitution Worksheet .pdf
1H & 13C NMRs / Electrophilic Aromatic Substitution Worksheet .pdf

6
Mar 1-5
Synthesis Project: Electrophilic Aromatic Substitution Reactions/ Acylation
Project Instructions .pdf
Electrophilic Aromatic Substitution Worksheet .pdf
1H & 13C NMRs / Electrophilic Aromatic Substitution Worksheet .pdf
7
Mar 8-12

Chiral Compounds and Green Chemistry: Reduction of a ketone by sodium borohydride and baker's yeast
Aldehydes & Ketones: Synthesis and Nucleophilic Addition wks.pdf

Aldehyde & Ketone Syntheses wks.pdf

Individual Aldol condensations

8
Mar 15-19

Chiral Compounds and Green Chemistry: Reduction of a ketone by sodium borohydride and baker's yeast
Aldehydes & Ketones: Synthesis and Nucleophilic Addition wks.pdf

Aldehyde & Ketone Syntheses wks.pdf


9

Mar 22-26

Chiral Compounds and Green Chemistry: Reduction of a ketone by sodium borohydride and baker's yeast

Aldehyde & Ketone Syntheses wks.pdf

Individual Aldol condensations

 


10
Mar 29-Apr 2

 

Ester Hydrolysis

DEET

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitutions .pdf


11
Apr 5-9

 

Holiday

 

 

Holiday

12
Apr 12-16

DEET

Carboxylic Acid Derivatives: Nucleophilic Acyl Substitutions .pdf

Literature Research

CPR


13
Apr. 19-23

Literature Research

CPR


14
Apr. 26-30

Flatulence

Carbohydrates Beano / Raffinose Sugars

Literature Research

CPR

15
May 3-7

Flatulence

Polymers

16
May 10-14

Lipids / Color/ Vision

Amino Acids/ Proteins/ Enzymes

17
May 17-21

Influenza Play

Lab Drawer / Equipment Check In
Aldrich-Kit with Ground Glass Joints

18
May 24-28

 

Finals

 


Skills & Operations:
Exercises / Activities / Experiments

1. Use & Care of Tapered Glassware.
2. Weighing Techniques: Tare & Care
3. Transferring Liquids.
4. Care, Handling & Storage of Chemicals.
5. Chemical Hygiene & Waste Disposal
6. Temperature: Measurement & Control.
7. Heating Methods.
8. Reflux.
9. Cooling Methods.
10. Methods of Addition (s, l, & g).
11. Filtration (Gravity).
12. Filtration (Vacuum/Aspirator).
13. Extraction.
14. Evaporation.
15. Rotevap: Recovery of Solvents.
16. Column Chromatography.
17. Thin-Layer Chromatography.
18. Gas Chromatography.
19. Washing Liquids.
20. Drying Liquids.
21. Drying Solids.
22. Drying and Trapping Gases.
23. Recrystallization.
24. Sublimation.
25. Steam Distillation.
26. Simple Distillation.
27. Vacuum Distillation.
28. Fractional Distillation.
29. Melting Point Determination.
30. Boiling Point Determination.
31. Refractive Index Determination.
32. Polarimetry: Optical Rotation.
33. IR: Infrared Spectrometry.
34. NMR: Nuclear Magnetic Resonance.
35. Ultraviolet-Visible Spectrometry.
36. Mass Spectrometry.


Safety:
SAFETY: General Regulations & Lab Guidelines

Safety Quiz Sheet & Acknowledgment

Molecular Modeling / WebMO

Electrophilic Aromatic Substitution / Friedel Crafts Acylation (Handouts)

Chiral Compounds and Green Chemistry: Reduction of a ketone by sodium borohydride and baker's yeast (Handouts)

Hydrolysis Rate of Esters (Handouts)

Insect Repellant: Deet Synthesis-Explorations 1, 2, 3

Minilab

Dimedone

Synthesis of a bioregulator: 1-phenyl-3-(4-diethylaminoethoxyphenyl)-2-(E)-propen-1-one (Handouts)

Flatulence / Carbohydrates / Digestion / Enzymes

Separation and Identification of Unknowns


Chem 226 Experiments & Skills: (Previous Course)
Experiment #1:  Extraction

Experiment #2: Recrystallization & Melting Point

Experiment #3:  Thin Layer Chromatography (TLC)
TLC of Analgesic Drug Components


Experiment #4: Synthesis of Salicylic Acid from Wintergreen


Experiment #5: Gas Chromatography & Fractional Distillation


Experiment #6: Enantiomeric Separation/ Resolution (Ibuprofen)
Optical Activity /Polarimetry: Part I & Part II
Optical Rotation I .pdf; Optical Rotation II .pdf


Experiment #7: Bromination of Cinnamic Acid

Experiment #8: Acetate Synthesis, Simple Distillation, Infrared Spectroscopy, GC

Experiment #9: Sn1 , Sn2 Reactions and Solvent Effects

Experiment #10: Essential Oils / Steam Distillation / Extraction

Experiment #11: Diels Alder reaction of maleic anhydride and furan

Experiment #12: Identification of Terpenoids

Experiment #13 : Colorful Grignard Reaction

 
   

Laboratory Techniques & Videos:

Techniques:
Extraction:
Description

Thin Layer Chromatography (TLC):
Procedure

Gas Cromatography:


Column Chromatography:

Simple & Fractional Distillation:

Vacuum Distillation:

Filtration:

Reflux:

Recrystallization:

Melting Point:

Infrared Spectroscopy:

Rotary Evaporation:

Videos:
Extraction:
http://www.chem.ualberta.ca/%7Eorglabs/Procedures/Separation_Isolation/Videos.html
http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm (Reaction Work-Up I)
Thin Layer Chromatography (TLC):
http://www.oid.ucla.edu/Webcast/chemistry/index.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Gas Cromatography:
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Column Chromatography:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Simple & Fractional Distillation:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Vacuum Distillation:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Filtration:
http://www.chem.ualberta.ca/%7Eorglabs/Procedures/Filtration/Videos.html
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Reflux:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
Recrystallization:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Melting Point:
http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Infrared Spectroscopy:
http://www.oid.ucla.edu/Webcast/chemistry/index.html
Rotary Evaporation:

http://ocw.mit.edu/ans7870/resources/chemvideo/index.htm (Reaction Work-Up II)

 

 


Laboratory Experiments
These experiments have been adapted from standard types of experiments commonly performed in organic chemistry courses throughout North America. They are derived from the non-copyrighted, open Web source materials kindly made available by a large number of notable educators/professors who generously share their creativity, time, efforts, and excellent materials. Their institutions include: University of Colorado, Boulder; McMaster University; University of Alberta; University of Calgary; Reed College, Barnard University; Massachusettes Institute of Technology; University of California, Los Angeles; Dakota State University; Wellesley University; University of California, Berkeley; Mount Holyoke College, Manhattan College.

Exercises / Worksheets / Tutorials
:

Spectroscopy Tables pdf




LABORATORY:
Molecular model of the spiral structure formed by the HMW subunits of glutenin.
The model was developed by Drs. O. Parchment and D. Osguthorpe at the University of Bath, U.K.
Peter Shewry, et. al., http://www.pbi.nrc.ca/bulletin/sept97/intro.html

            End of Course Survey: (Anonymous survey)