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360rptbk-05

Course Number: CHEM 360, Fall 2009

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Chemistry 360 Organic Chemistry II ________________________________________________________________________ Report Book 2005/2006 Athabasca University Course team Report Book Authors: Report Book Contributors: Laboratory Technician: Course Coordinator: Mr. Robert D. Carmichael and Dr. Lois M. Browne Ms. Aimee Caouette Ms. Elaine Goth-Birkigt Mr. Jim Robinson Every effort has been taken to ensure that these...

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360 Organic Chemistry Chemistry II ________________________________________________________________________ Report Book 2005/2006 Athabasca University Course team Report Book Authors: Report Book Contributors: Laboratory Technician: Course Coordinator: Mr. Robert D. Carmichael and Dr. Lois M. Browne Ms. Aimee Caouette Ms. Elaine Goth-Birkigt Mr. Jim Robinson Every effort has been taken to ensure that these materials comply with the requirements of copyright clearances and appropriate credits. Athabasca University will attempt to incorporate in future printings any corrections which are communicated to it. The inclusion of any material in this publication is strictly in accord with the consents obtained and Athabasca University does not authorize or license any further reproduction or use without the consent of the copyright holder. Athabasca University 2005 All rights reserved Printed in Canada ii CHEM 360 Report Book Contents _______________________________________________________________________________ General Introduction Report Book Structure Acknowledgements 1 3 4 5 5 6-13 14 14 15-21 22 22 23-30 31 31 32-39 40 40 41 42 42 43-50 Experiment 10 Fisher Esterification Reaction Pre-lab Questions Experiment 10 Lab Report Experiment 11 Reactions of Common Functional Groups: Part II: Alcohols and Aryl Halides Pre-lab Questions Experiment 11 Lab Report Experiment 12 Reduction of Benzophenone Pre-lab Questions Experiment 12 Lab Report Experiment 13 Aldol Condensations Pre-lab Questions Experiment 13 Lab Report Experiment 14 1H-NMR Tutorial Pre-lab Questions Experiment 14 Lab Report Experiment 15 Reactions of Common Functional Groups Part III: Aldehydes and Ketones Pre-lab Questions Experiment 15 Lab Report iii CHEM 360 Report Book Contents (cont.) _______________________________________________________________________________ Experiment 16 Grignard Reaction Pre-lab Questions Experiment 16 Lab Report 51 51 52-62 63 63 64-77 78 82 Experiment 17 Multi-step Synthesis of Benzocaine Pre-lab Questions Experiment 17 Lab Report Table of Reagents CHEM 360 Questionnaire iv CHEM360 Report Book 2005-06 Introduction Welcome to Organic Chemistry 360s Laboratory Report Workbook This Report Book, along with the 'Chemistry 360 Lab Manual', will help you prepare for the two weekends (~30h) of supervised lab instruction. All preparatory work in this report book (~12 h to finish, see list on page 3), must be completed and shown to the Chemistry Lab Co-ordinator / Lab Instructor prior to beginning the labs. In order to successfully complete the laboratory component, please be aware of the following 4 step process of instruction. It is the intention of this Chem360 Report Workbook to provide you with the means of completing all four steps. Step 1: First we tell you what you are going to do. Find out by reading the lab manual, doing the pre-lab questions in this report book, and filling out the Table of Reagents etc., i.e., preparing for the labs at home. (By doing so you are able to work more efficiently in the lab and the over-all time spent in the supervised lab can be reduced to ~20 hours from the usually 32 hours.) Step 2: Next we show you how to do it. When you come to the lab, a lab instructor will give a safety orientation, followed by a series of mini lab lectures on each experiment. Various techniques will be demonstrated and you will be shown how to handle chemicals, dispose of hazardous waste, and operate the equipment. 1 Introduction Step 3: Lab Time: Now you do what you've read, been told, and shown. This is the time you spend in the lab performing your experiments, making your products, and recording your results in this report workbook CHEM360 Report Book 2005-06 Step 4: Finally, you tell us what you did. This is the report writing stage. Actually most of your reports will have been written while in the lab. At home you will only have to do your calculations, write your discussion and conclusion and answer the questions at the end of each experiment. 2 CHEM360 Report Book 2005-06 Introduction Report Book Structure and How to Prepare for the Labs: This CHEM360 Report Book is to used in conjunction with the CHEM360 Organic Chemistry II Lab Manual. It consists of an Introduction, Experiment Report Forms, Table of Reagents and a Course Evaluation. The reports are to be completed one month after of the lab session you attended. As a safety precaution, it is advisable to photocopy your reports before mailing them to your tutor for marking. Note: the marked reports are not returned to you. How to best do the Report Book Exercises 1. 2. 3. 4. 5. First read through the lab manual introduction, and then answer the pre-lab questions for each experiment. Complete the Objectives in the Experiment Report. Complete the Procedure (Refer to lab manual pages) and make a flowchart if necessary. Complete the Table of Reagents for each experiment (detach a copy of the TOR to avoid flipping back and forth) You are now ready to come to the lab and do the experimental work. Note: Each experiment in the report book has the following headings: Report Book Heading 1. Experiment Prelab Questions Purpose and Use Answer these questions to help you prepare and understand what you are doing in the lab. In order to answer these questions you will have to consult the CHEM360 Lab Manual, and to read the 'Introduction to Concept', and 'Background Information' sections of this manual. Complete all the questions, and submit for review just before attending the lab Objectives Lists what you should learn from the lab. (see also lab manual). Use this information to fill in 'Objectives' in your Lab Write-up. When appropriate, write out any chemical reactions. Introduction Briefly state how the objectives of the experiment will be achieved and provide the relevant background information. Procedure Refer to the lab manual and only note any modifications or changes. Fill out the Table of reagents. Use the flowchart procedural step table to record your work and observations. The sections of your report shown below are completed while doing the experiment, or at home after the lab session. Results While doing or immediately after your experiment, record your results in this section of the report. Discussion and Conclusion As soon after the lab as possible, discuss your results in light of the objectives, and make the appropriate conclusions. Remember to discuss sources of potential error and loss. Post Lab Questions Answer these questions to prove you understand what you did in the lab. To be completed after the experiment is finished. Submit your answers by mail along with the Course Evaluation. 2. 3. 4. 5. 6. 7. 3 Introduction CHEM360 Report Book 2005-06 Acknowledgements: The grateful authors wish to especially thank Ms. Aimee Caouette for all the artwork. Athabasca University also wishes to thank Drs. K. Tanabe and T. Tamura and for their permission to use the IR and 1H-NMR Spectra used in our lab manual and report book (pp. 50, 62). They were obtained from the SDBS web site: http://www.aist.go.jp/RIODB/SDBS/ (29-Sep-1999). Each experiment in CHEM360 has been modified and rewritten from other sources, keeping the particular needs of Athabasca University students in mind. The procedures described in this manual have been checked in our Athabasca laboratories by Klaus Thomson, Nyron Jaleel, Jerry Pyrozko, Roger Klemm, Glen Conlin, and Robert Carmichael. Special thanks to Ms. Aimee Caouette for her help on the Infrared Tutorial (Summer 1999). Also thanks to Mr. Douglas Woudstra and Mr. James Taylor (CHEM360 students 2004-05) for their helpful suggestions to improve the report book. The comments and suggestions received from all the individuals mentioned above were greatly appreciated by the Course Co-ordinator. The following sources are also hereby acknowledged: Laboratory Manual, Chemistry 320, Athabasca University, 1984. Laboratory Manual, Chemistry 320, University of British Columbia, 1972-73. Laboratory Manual, Chemistry 240, Dalhousie University, 1973. Laboratory Manual, Chemistry 240A/B, Sir Wilfred Grenfell College, 1982-83. Laboratory Manual, Chemistry 240, Memorial University of Newfoundland, 1976-77. L.M. Browne, 1998. Laboratory Manual, Chemistry 161, University of Alberta. L.M. Browne, 1998. Laboratory Manual, Chemistry 163, University of Alberta. L.M. Browne, 1993. Laboratory Manual, Chemistry 361, University of Alberta. Lehman, J.W. 1999. Operation Organic Chemistry: A Problem-Solving Approach to the Laboratory Course, 3rd ed., Prentice Hall, New Jersey. Mayo, D.W., R.M. Pike, and S.S. Butcher. 1989. Microscale Organic Laboratory, 2nd ed., John Wiley and Sons, Toronto, pp.229-232. McMurry, J., 1992. Organic Chemistry, 3rd ed., Brooks/Cole Publishing Company, Pacific Grove, CA. Weast, R.C. et al, 1974. CRC Handbook of Chemistry and Physics, 65th ed., CRC Press, Inc., Boca Raton, FL. 4 CHEM360 Report Book 2005-06 Exp.10 CHEM360 Experiment 10 Report Student Name:___________________ Experiment 10 Prelab Questions: 1. What are the two starting reagents used in a Fisher Esterification? a) carboxylic acid and a ketone b) alcohol and an ester c) alcohol and a carboxylic acid d) carboxylic acid and an ester Is the Fisher esterification reaction reversible? a) yes b) no Date:___________ ID Number:___________ 2. 3. How long must you reflux the reaction in order to maximize the amount of product formed? a) 30 min. b) 45-60 min. c) 52.5 min. d) >60 min. (The longer the better!) What acts as the nucleophile, and what acts as the electrophile in this reaction? a) Nu = sulphuric acid, E = acetic acid b) Nu = isoamyl alcohol, E = acetic acid (protonated form) c) Nu = isoamyl alcohol, E = acetic acid d) Nu = acetic acid, E = isoamyl acetate What gas is evolved during the reaction workup phase when you wash with 5% Na2CO3 (Procedure Step C-5)? a) H2 (g) b) N2 (g) c) O2 (g) d) CO2 (g) How is the ester product purified and characterized? a) Yield, refractive index, % yield, infrared spectral analysis b) Boiling point, refractive index, and infrared spectral analysis c) Yield, boiling point, refractive index, % yield, and infrared spectral analysis What major differences in absorption bands would you expect to see in the infrared spectra of isoamyl alcohol, and isoamyl acetate, the ester product? a) Broad 3300 cm-1 absorption for alcohol, sharp ~1740 cm-1 C=O of carbonyl in ester b) Sharp ~2900 cm-1 absorption(s) for sp3 C-H, no ~2900 cm-1 absorption for sp3 C-H in ester. c) Sharp 3300 cm-1 absorption for alcohol, broad ~1740 cm-1 C=O of carbonyl in ester . d) Sharp ~1200 cm-1 absorption for C-O of alcohol, none for the ester . 4. 5. 6. 7. 5 Exp.10 CHEM360 Report Book 2005-06 CHEM360 Experiment 10 Report Student Name:___________________ Date:___________ ID Number:___________ Title: Objective(s): Equation(s): (General and specific reaction, draw structures, and provide names) 6 CHEM360 Report Book 2005-06 Exp.10 Introduction: 7 Exp.10 CHEM360 Report Book 2005-06 Procedure: (Ref: ) Changes/Modification: Procedure for the Fisher esterification of acetic acid with isoamyl alcohol. Procedural Step Record amounts of reagents used. Observations/Comments/Inferences Table of Reagents for Experiment 10 Fisher Esterification. Reagent Formula Mwt. (g/mol) d (g/ml) Mp (C) Bp (C) Haz. Properties Acetic acid, glacial (conc.) 17.4 M Isoamyl alcohol (3-methyl -1-butanol) Sulfuric acid, conc. 18 M Distilled water Diethyl ether 5% sodium carbonate (aq) Sat. sodium chloride (aq) (brine) Calcium chloride (anhydr) acetone, wash Isoamyl acetate (CH3)2CH(CH2)2OH 88.15 1.840 18.02 1.000 0 130 Irritant H2SO4 H2O 100 none Na2CO3 (aq) NaCl (aq) CaCl2 CH3CO2C5H11 130.19 142 8 CHEM360 Report Book 2005-06 EXPERIMENT 10 FLOW CHART REAGENT PROCEDURE / STEP Exp.10 OBSERVATION Amt = _______ Amt = _______ Amt = _______ Add boiling stones Reflux for 45-60 min Cool, transfer to sep. fun. Add dH2O Amt = ______ Add diethyl ether (ester extractn) Amt = ____ Add dH2O wash Amt = ______ 5% Na2CO3 wash Check pH. Amt = ____ Brine wash Amt = ______ Add drying agent CaCl2 (anhydr.) Distil Crude Ester (add boiling stones) 9 Product Characterization by: ________________ Exp.10 CHEM360 Report Book 2005-06 Experiment 10 Results: Table 2. Summary Table of Observations: Procedural Step Comment or Observation and Inference Table 3. Table of Product Data for Isoamyl acetate, Fisher Esterification Product. Table 3. presents the summary of the results of the experiment. The calculations for limiting reagent, theoretical yield and percent yield are shown below the table. Note: _________________ was found to be the limiting reagent. Refractive Theoretical Yield % Yield Appearance Boiling Refractive Index^ Yield Mass of Liquid Pt.* Index (nD20) (g) (g) nD obs. (C) Isoamyl acetate *Corrected for barometric pressure effects using the formula ^Corrected to 20C using the formula: Limiting Reagent and Theoretical Yield Calculation: Moles of acetic acid used in the reaction = Moles of isoamyl alcohol used in the reaction = Theoretical Yield of iosamyl acetate = % Yield Calculation: 10 CHEM360 Report Book 2005-06 Table 4. Tabulation of Characteristic Infrared Absorptions for the starting regents, and product. Exp.10 Table 4 contains the results of the Infrared Spectral Analyses for the isoamyl alcohol, acetic acid, and isoamyl acetate as obtained by thin film in a FTIR. See also attached spectra for peak numbering and identification. Peak Code# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strg,, med., or weak) Isoamyl alcohol >3000 cm-1 Region 3000-2000 cm-1 Region 2000-1400 cm-1 Region Fingerprint Region Functional Groups Absent: Functional Group Indicated Acetic acid >3000 cm-1 Region 3000-2000 cm-1 Region 2000-1400 cm-1 Region Fingerprint Region Functional Groups Absent: Peak Code# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strg,, med., or weak) Functional Group Indicated Isoamyl acetate >3000 cm-1 Region 3000-2000 cm-1 Region 2000-1400 cm-1 Region Fingerprint Region Functional Groups Absent: Peak Code# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strg,, med., or weak) Functional Group Indicated 11 Exp.10 CHEM360 Report Book 2005-06 Discussion: Comments on reasons for yield (high or low), purity (high or low), sources of error, infrared spectrum results: Conclusion: Structure of Product 12 CHEM360 Report Book 2005-06 Exp.10 Experiment 10 Questions: 1. If the cost of both the alcohol and carboxylic acid were prohibitive, how would you maximize the yield of your Fischer esterification product while keeping costs down? 2. Why did you wash your product with water (3X), before washing it with the solution of sodium hydrogen carbonate? What was the purpose of washing with sodium hydrogen carbonate? 3. Explain the function of the acid catalyst in a Fisher esterification reaction. 4. What would the reactants be to produce isoamyl valerate via Fischer esterification reaction? 13 Exp.11 CHEM360 Report Book 2005-06 CHEM360 Experiment 11 Report Student Name:___________________ Experiment 11 Prelab Questions: 1. Date:___________ ID Number:___________ What is the oxidizing agent used to detect primary and secondary alcohols? a) sulphuric acid b) sodium dichromate c) mixture of sulphuric acid and sodium dichromate d) the alcohol What is the organic product of the reaction of Lucas reagent with an alcohol? a) ketone b) silver halide c) water d) alkyl halide What type of alcohol would be positive in both the Dichromate and Lucas Reagent tests? a. phenol b) primary c) secondary d) tertiary What does SN1 stand for? 2. 3. 4. 5. What does SN2 stand for? 6. Why is the silver nitrate test a good one to observe SN1 reaction mechanism behaviour? 7. Why is the sodium iodide in acetone test a good one to observe SN2 reaction mechanism behaviour? 14 CHEM360 Report Book 2005-06 Exp.11 CHEM360 Experiment 11 Report Student Name:___________________ Title: Date:___________ ID Number:___________ Objective(s): Introduction: 15 Exp.11 CHEM360 Report Book 2005-06 Procedure: (Ref: ) Changes/Modification: Table 1. Table of Reagents for Experiment 11. Reagent 1-butanol 2-butanol 2-methyl-2-propanol Cyclohexanol 1-chlorobutane 2-chlorobutane 2-chloro-2-methylpropane 1-bromobutane 2-bromobutane Chlorobenzene benzyl chloride 3-chloro-1-butene Bromocylclohexane Bromocyclopentane -bromostyrene sodium dichromate sulfuric acid Lucas reagent zinc chloride, anhydrous hydrochloric acid, conc. sodium iodide silver nitrate nitric acid Acetone ethanol ZnCl2 HCl NaI AgNO3 HNO3 CH3COCH3 CH3CH2OH Formula C4H9OH C4H9OH C4H9OH C6H11OH C4H9Cl C4H9Cl C4H9Cl C4H9Br C4H9Br C6H5Cl C6H5CH2Cl C4H7Cl C6H11Br C5H9Br C6H5CHCHBr Na2Cr2O7 H2SO4 Mwt. 74.12 74.12 74.12 100.16 92.57 92.57 92.57 136.9 136.9 122.4 126.59 90.55 163.06 149.04 183.05 261.6 98.08 Solution of ZnCl2 and HCl 136.28 36.46 149.9 169.8 63.01 58.09 46.07 1.400 0.818 0.785 56.5 78.5 2.91 1.20 283 732 (110) Vol/Mass 4 drops 4 drops 4 drops 4 drops 8 drops 8 drops 8 drops 8 drops 8 drops 8 drops 8 drops 8 drops 8 drops 8 drops 8 drops 12 mL d 0.810 0.807 0.7887 0.9624 0.8862 0.8732 0.8420 1.2758 1.2585 1.1058 1.1002 0.8978 1.3359 1.3873 1.4269 7 -56.5 25.5 25.1 -123 -131 -25.4 -112 -112 -45.6 -39 mp -89.5 bp 117-118 100 82.3 161.1 78.4 68.2 52 101.6 91.2 132 179.3 64-65 166.2 136.7 219 Haz. Properties Flamm., Irritant Flamm., Irritant Flamm., Irritant Irritant, Hygroscopic Flammable Flammable Flammable Flammable, Irritant Flammable, Irritant Flammable, Irritant Toxic, Cancer susp.agent Flamm., Lachrymator Flammable, Irritant Flammable, Irritant Irritant Toxic, Cancer susp.agent Corrosive, Toxic, Oxidizer Toxic, Irritant Corrosive, Toxic Corrosive, Highly toxic Mosit. Sens., Irritant Highly toxic, Oxidizer Corrosive, Oxidizer Flammable, Irritant Flammable, Poison 16 CHEM360 Report Book 2005-06 Exp.11 Experiment 11 Part A Results: Reactions of Alcohols (1, 2, and 3) Test Substance 1-butanol 1. Alcohol Oxidation by Sodium Dichromate Observation Inference Equation 2-butanol cyclohexanol 2-methyl-2-propanol Test Substance 1-butanol Observation 2. Lucas Reagent Test Inference Equation 2-butanol cyclohexanol 2-methyl-2-propanol 17 Exp.11 CHEM360 Report Book 2005-06 Experiment 11 Part B Results: Reactions of Alkyl Halides Test Substance 1-chlorobutane Silver Nitrate Test (SN1 Mechanism) Observation Inference Equation 2-chlorobutane 2-chloro-2methylpropane 1-bromobutane 2-bromobutane Chlorobenzene Benzyl chloride 3-chloro-1-butene Bromocyclohexane Bromocyclopentane -bromostyrene 18 CHEM360 Report Book 2005-06 Exp.11 Experiment 11 Part B Results: (cont.) Test Substance 1-chlorobutane Sodium Iodide/Acetone Test (SN2 Mechanism) Observation Inference Equation 2-chlorobutane 2-chloro-2methylpropane 1-bromobutane 2-bromobutane Chlorobenzene Benzyl chloride 3-chloro-1-butene Bromocyclohexane Bromocyclopentane -bromostyrene 19 Exp.11 CHEM360 Report Book 2005-06 Conclusion: 20 CHEM360 Report Book 2005-06 Exp.11 Experiment 11 Questions: 1. There are four isomeric alcohols having the formula C4H10O, and in this experiment you investigated the properties of three of them. How would you expect the fourth isomer to behave when treated with (i) acidic sodium dichromate, and (ii) Lucas reagent? On the basis of your results, arrange the eleven halogen-containing compounds in order of decreasing reactivity in (i) SN1 reactions and (ii) SN2 reactions. a. What results would you expect to observe when benzyl alcohol, C6H5CH2OH, is treated with (i) acidic sodium dichromate, and (ii) Lucas reagent? What results would you expect to obtain when 1-chloro-2,2-dimethylpropane is treated with (i) ethanolic silver nitrate, and (ii) sodium iodide in acetone? 2. 3. b. 21 Exp.12 CHEM360 Report Book 2005-06 CHEM360 Experiment 12 Report Student Name:___________________ Experiment 12 Prelab Questions: 1. Date:___________ ID Number:___________ Why must you prepare the two main reagents, sodium borohydride and benzophenone, separately and then mix them together? 2. Why do you add the sodium borohydride slowly to the benzophenone? 3. What is the purpose of adding the hydrochloric acid/ice in the procedure? 4. Why is hexane used as a recrystallization solvent? 5. What is the purpose of performing a TLC on the crude and recrystallized product, and benzophenone? 22 CHEM360 Report Book 2005-06 Exp.12 CHEM360 Experiment 12 Report Student Name:___________________ Title: Objective(s): Date:___________ ID Number:___________ Reaction Equation: (structures and names) Introduction: 23 Exp.12 CHEM360 Report Book 2005-06 Procedure: (Ref: author surname, initials, date. Title of text, publisher, pages) Changes/Modification: Part A: Reduction of Benzophenone Procedural Step Preparation of organic reagent Preparation of reducing agent Observations/Comments/Inferences Part B: Thin Layer Chromatography of Reagent and Product. Procedural Step 1. Preparation of eluent 2. Preparation of spotting solutions 3. Number of spots per lane: 4. Appearance of developed TLC Observations/Comments/Inferences Table 1. Table of Reagents for Exp. 12 Reagent Benzophenone (or diphenylketone) Sodium borohydride Methanol Hydrochloric acid (conc. = 12M) Hexane Ethyl acetate Ligroin Chloroform Iodine Diphenylmethanol (or benzhydrol) Formula C6H5COC6H5 NaBH4 CH3OH HCl C6H14 C2H5CO2 C2H5 Mineral spiritis CHCl3 I2 119.39 253.81 Mwt. 182.22 37.83 32.04 36.46 86.18 88.11 2 mL 10 mL 3 mL trace ? Vol/Mass d NA NA 1.3288 1.20 0.659 0.902 0.656 1.500 NA moles mp bp NA NA 65 Haz. Properties 400 -93.9 NA NA NA NA NA 133 69 77 60-80 61.3 NA NA NA = not applicable 24 CHEM360 Report Book 2005-06 SAMPLE EXPERIMENT 12 FLOW CHART REAGENT PROCEDURE / STEP Exp.12 OBSERVATION _____ g Sodium borohydride 25 mL Erlenmeyer Flask 30g ice and 3mL conc.HCl ___ mL Hexane Recrystallize Product Characterization by: ________________ 25 Exp.12 CHEM360 Report Book 2005-06 Experiment 12 Results: Table 2. Summary Table of Observations: Procedural Step Comment or Observation Table 3. Table of Product Data for Diphenylmethanol, the Carbonyl Reduction Product. Table 3. presents the summary of the results of the experiment. The calculations for limiting reagent, theoretical yield and percent yield are shown below the table. Note: _________________ was found to be the limiting reagent. Product Name Yield Appearance Observed Lit. Melting Theoretical % Yield (Mass in g) of Solid Melting Pt.* Pt. Yield (g) (C) (C) *uncalibrated thermometer used. Limiting Reagent and Theoretical Yield Calculation: Moles of benzophenone used in the reaction = Moles of sodium borohydride used in the reaction = Theoretical Yield of iosamyl acetate = % Yield Calculation: 26 CHEM360 Report Book 2005-06 Exp.12 Table 4. Infrared Spectrum Data Analysis (see attached spectra) Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Fig 1. TLC Analysis of Benzophenone, Crude and Recrystallized Diphenylmethanol 27 Exp.12 CHEM360 Report Book 2005-06 Discussion: Comments on and reasons for yield (high/med/low), purity (high/med/low), sources of error (uncalibrated thermometer?, side reactions?): Conclusion: 28 Structure of Product CHEM360 Report Book 2005-06 Exp.12 29 Exp.12 CHEM360 Report Book 2005-06 Experiment 12 Questions: 1. Aldehydes and ketones can be reduced to alcohols using hydrogen gas and a metal catalyst. Suggest two reasons why the use of sodium borohydride is preferred over the catalytic hydrogenation in order to prepare diphenylmethanol from benzophenone. 2. In this experiment, you destroyed the excess sodium borohydride by reacting it with hydrochloric acid (Part A, Step 5). What gas was evolved during the process? Write a balanced equation for the reaction that occurred. (Hint: one of the products was boric acid). 30 CHEM360 Report Book 2005-06 Exp.13 CHEM360 Experiment 13 Report Student Name:___________________ Experiment 13 Prelab Questions 1. Aldol condensation reactions are what type of reaction? Date:___________ ID Number:___________ 2. What is the purpose of adding the reagent 95% ethanol (in water) to the reaction mixture of ketone and aldehyde? 3. What is the purpose of adding the reagent 1.0 M NaOH to the reaction mixture of ketone and aldehyde? 4. Will your product be essentially pure after cooling the flask in ice in Step 2 of the procedure? 5. Will your product be essentially pure after washing your product with ice cold 95% ethanol, ice cold 95% ethanol + 4% acetic acid and again with ice cold 95% ethanol in Step 3 of the procedure? 6. What must the washing solutions be ice-cold in Step 3 of the procedure? 7. How will you know which solvent (95% ethanol or toluene) is more suitable for the recrystallization of your product? 31 Exp.13 CHEM360 Report Book 2005-06 CHEM360 Experiment 13 Report Student Name:___________________ Title: Objective(s): Date:___________ ID Number:___________ Reaction Equation: (structures and names) Introduction: 32 CHEM360 Report Book 2005-06 Exp.13 Introduction: (cont.) 33 Exp.13 CHEM360 Report Book 2005-06 Procedure: (Ref: author surname, initials, date. Title of text, publisher, pages) Changes/Modification: Mixed Aldol Condensation Reaction Observations Procedural Step Observations/Comments/Inferences Table 1. Table of Reagents for Exp. 13 Reagent Formula Mwt. d mp bp Haz. Properties Benzaldehyde 4-methylbenzaldehyde 4-methoxybenzaldehyde Cinnamaldehyde Acetone Cyclopentanone Cyclohexanone 4-methylcyclohexanone Ethanol Sodium hydroxide Acetic acid Toluene Benzalacetone Dibenzalacetone Dibenzalcyclohexanone Dibenzalcyclopentanone Chloroform Carbon tetrachloride CHCl3 CCl4 CH3C6H4CHO CH3OC6H4CHO C6H5CH=CHCHO CH3COCH3 C5H8O C6H10O CH3C6H9O CH3CH2OH NaOH (1M) CH3COOH C6H5CH3 C6H5CHCHCOCH3 1.044 1.019 1.119 1.048 0.818 0.951 0.947 0.914 0.785 ~1.00 1.049 0.865 179.5 204-205 248 248 56.5 130.6 155 169-171 78.5 118.1 110.6 34 CHEM360 Report Book 2005-06 SAMPLE EXPERIMENT 13 FLOW CHART REAGENT PROCEDURE / STEP Exp.13 OBSERVATION 10 mL 95% ethanol 10 mL 95%EtOH + 4% Acetic acid 10 mL 95% ethanol Select Solvent =______________ Recrystallize from Product Characterization by: 35 Exp.13 CHEM360 Report Book 2005-06 Experiment 13 Results: Table 2. Summary Table of Observations: Procedural Step Comment/Observation/Inferences Table 3. Table of Data for Aldol Condensation Product. Table 3 presents the summary of the results of the experiment. The calculations for limiting reagent, theoretical yield and percent yield are shown below the table. Note: Both reagents are added in equal stoichiometric amounts. The _______________________ was used as the limiting reagent as it is a 1:1 ratio with the product. Product Name Yield Mass (g) Appearance of Solid Melting Pt.* (C) Literature Melting Pt. (C) Theoretical Yield (g) % Yield *Uncorrected for temperature calibration Limiting Reagent and Theoretical Yield Calculation: Moles of ketone actually used in the reaction = Moles of aldehyde actually used in the reaction = Theoretical Yield of Aldol product = % Yield Calculation: 36 CHEM360 Report Book 2005-06 Exp.13 Table 4. Infrared Spectrum Data Analysis (see attached spectra) Absorption Peak Wavenumber Aldehyde = Band# Shape (cm-1) (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Ketone = Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: Aldol Product = Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, medium or weak) Functional Group Indicated Functional Group absent: 37 Exp.13 CHEM360 Report Book 2005-06 Discussion: Comments on and give reasons for high or low yield and purity, and sources of error (practical and theoretical), etc.: Conclusion: Structure of Product 38 CHEM360 Report Book 2005-06 Exp.13 Experiment 13 Questions: 1. The product obtained in this experiment results from a crossed condensation between an aldehyde and a ketone. Identify two other base-initiated reactions that could conceivably occur involving either or both of these reactants. Suggest reasons why these reactions do not result in the formation of large quantities of by-products. 39 Exp.14 CHEM360 Report Book 2005-06 CHEM360 Experiment 14 Report Student Name:___________________ Experiment 14 Prelab Questions: 1. 1 Date:___________ ID #:___________ H-NMR is an abbreviation meaning: 2. What types of information are to be found in a 1H-NMR spectrum? 3. True or False. Chemical shifts are the result shielding and deshielding of the environment the proton finds around it. 4. True or False. The N=n+1 rule is used to determine the number of neighbouring H if you know the signal splitting or vice versa. 5. What is the purpose of adding tetramethylsilane (TMS) to a 1H-NMR sample prior to determining its spectrum? 6. A very common splitting pattern seen in a 1H-NMR spectrum is the 2H quartet coupled to a 3H triplet. What of the following molecular fragments does this usually represent: a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group? Another very common splitting pattern seen in a 1H-NMR spectrum is a 1H septet coupled to a 6H doublet. What of the following molecular fragments does this usually represent: a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group? 7. 40 CHEM360 Report Book 2005-06 Exp.14 CHEM360 Experiment 14 Report Student Name:___________________ Title: Objective(s): Date:___________ ID Number:___________ Procedure: (Ref: ) Changes/Modification: ATTACH YOUR 4 UNKNOWN IR/NMR SPECTRA PROBLEMS TO THIS TITLE PAGE. 41 Exp.15 CHEM360 Report Book 2005-06 CHEM360 Experiment 15 Report Student Name:___________________ Experiment 15 Prelab Questions 1. What does the Bradys Test detect? Date:___________ ID Number:___________ 2. What does the Tollens Test detect? 3. What does the Schiffs Test detect? 4. What does the Iodoform Test Detect? 5. Which of the following compounds gives a positive reaction to three of the tests above? a) aldehyde b) cyclohexene c) pentane d) acetone If the compound does not react in any of the four above tests, the compound is most likely to be a(n): a) ester b) carboxylic acid c) alkane d) amide 6. 42 CHEM360 Report Book 2005-06 Exp.15 CHEM360 Experiment 15 Report Student Name:___________________ Title: Objective(s): Date:___________ ID Number:___________ Reaction Equations: 43 Exp.15 CHEM360 Report Book 2005-06 Introduction: 44 CHEM360 Report Book 2005-06 Exp.15 Procedure: (Ref: ) Changes/Modification: Table 1. Table of Reagents for Experiment 15. Reagent Benzaldehyde 4-methylbenzaldehyde 4-methoxybenzaldehyde trans-cinnamaldehyde Acetone Cyclopentanone Cyclohexanone 4-methylcyclohexanone Formaldehyde Acetophenone 1-butanol 2-butanol Methanol Brady's Reagent 2,4-dinitrophenyl hydrazine Sulfuric acid, conc. (18 M) Ethanol, 95% Tollen's Reagent Schiff's Reagent Ammonium hydroxide Silver nitrate Nitric acid Sodium hydroxide Iodine in potassium iodide Formula C6H5CHO CH3C6H4CHO CH3OC6H4CHO C6H5CHCHCHO CH3COCH3 C5H8 (=O) C6H10 (=O) CH3C6H9 (=O) HCHO C6H5COCH3 CH3(CH2)3OH C2H5CH(OH)CH3 CH3OH Solution (O2N)2C6H3NHNH2 H2SO4 CH3CH2OH Solution Solution NH4OH AgNO3, 0.3 M HNO3 NaOH, 3 M I2 in KI 35.05 169.87 63.01 40.00 ~1.00 198.14 98.08 46.07 1.840 0.785 78.5 Mwt. 106.12 120.15 136.15 132.16 58.08 84.12 98.15 112.17 30.03 120.15 74.12 74.12 32.04 d 1.044 1.019 1.119 1.048 0.791 0.951 0.947 0.914 1.083 1.030 0.810 0.807 0.791 -98 19-20 -90 202 117.7 99-100 64.7 -94 -51 -47 -1 mp -26 bp 179.5 204-205 248 248 56 130-131 155 169-171 Haz. Properties See hydrazine, 2,4-dinitrophenyl See ammonia + silver nitrate mixture of roseaniline hydrochloride and sulfur dioxide, Toxic 0.90 4.352 212 45 Exp.15 CHEM360 Report Book 2005-06 Experiment Part 15 A Results: Test Substance Aldehyde = Bradys Test 2,4-dinitrophenylhydrazine Observation Inference Equation Ketone = Positive control Negative control Part B Results: Test Substance Aldehyde = Tollens Test - Silver Mirror Observation Inference Equation Ketone = Positive control Negative control 46 CHEM360 Report Book 2005-06 Exp.15 Part C Results: Test Substance Formaldehyde Observation Schiffs Test Inference Equation Aldehyde = Ketone = Test Substance Acetone Observation Iodoform Test Inference Equation Cyclohexanone Acetophenone 1 butanol 2-butanol 47 Exp.15 CHEM360 Report Book 2005-06 Conclusion: Comments on tests, sources of error, and false positives/negatives: 48 CHEM360 Report Book 2005-06 Exp.15 Experiment 15 Questions: 1. Write a balanced equation for the reaction of acetaldehyde (i.e. ethanal) with ammoniacal silver nitrate. Remember that this is a redox reaction. 2. Outline a systematic functional group test procedure that would enable you to distinguish among hexanal, 2-hexanone, 3-hexanone, 2-hexanol, and cyclohexanol. 3. Aldehydes and ketones can also be easily distinguished by their infrared spectra and their identity deduced from their 1H-NMR spectra. Explain why this is. 4. From the following results, identify the unknown compounds. a) Compound A: 2,4-DNPH positive, Tollens Test positive, Schiff's test positive, Iodoform negative (see Spectrum (A) next page). b) Compound B: 2,4-DNPH positive, Tollens Test negative, Schiff's test negative, Iodoform positive (see Spectrum (B) next page). 49 Exp.15 Spectrum (A): 1H-NMR, 400 MHz in CDCl3 CHEM360 Report Book 2005-06 Molecular Formula C8H8O2 , 9.9 = 1H, 7.8 = 2H, 7.0 = 2H, 3.9 = 3H. Spectrum (B): 1H-NMR, 90 MHz in CDCl3 Molecular Formula C8H8O , 7.9 = 2H, 7.3-7.7 = 3H, 2.6 = 3H. 50 CHEM360 Report Book 2005-06 Exp.16 CHEM360 Experiment 16 Report Student Name:___________________ Experiment 16 Prelab Questions 1. Date:___________ ID Number:___________ What is the purpose of the magnesium used in the Grignard Reaction? 2. What is the purpose of the diethyl ether used in the Grignard Reaction? 3. What are two of the limitations of the Grignard Reaction? 4. What is the purpose of using 50mL 2M H2SO4 in Part C Step 1? 5. What layer will your product be in after addition of the diethyl ether in Part C Step 3? 6. What is the purpose of washing the organic layer with water in Part C Step 6? 7. What is the purpose of washing the organic layer with brine in the same Part C Step 6? 8. What is the purpose of adding anhydrous calcium chloride the organic layer with brine in the same Part C Step 6? 9. What is the purpose of using ligroin in Part C Step 7? 10. A flowchart is not really necessary for this experiment. ( True or False ). 51 Exp.16 CHEM360 Report Book 2005-06 CHEM360 Experiment 16 Report Student Name:___________________ Title: Objective(s): Date:___________ ID Number:___________ Reaction Equation(s): 52 CHEM360 Report Book 2005-06 Exp.16 Introduction: 53 Exp.16 CHEM360 Report Book 2005-06 Procedure: (Ref: ) Changes/Modification: A. Procedure for formation of Grignard Reagent. Procedural Step Observations/Comments/Inferences B. Procedure for the reaction of the Grignard Reagent with ethyl benzoate to form Tiphenylmethanol. Procedural Step Observations/Comments/Inferences C. Procedure for isolation of Triphenylmethanol. Procedural Step Observations/Comments/Inferences 54 CHEM360 Report Book 2005-06 Exp.16 D. Procedure for the observation of the carbocation. Procedural Step Observations/Comments/Inferences E. Procedure for assessment of product purity by Thin Layer Chromatography. Procedural Step Observations/Comments/Inferences 55 Exp.16 CHEM360 Report Book 2005-06 Procedure: (cont.) Table 1. Table of Reagents for Experiment 16. Reagent Formula Mwt. d mp bp Haz. Properties Bromobenzene Magnesium Ethyl benzoate Diethyl ether Sulfuric acid, 2M Sodium H carbonate Sodium sulfate, anhyd Dichloromethane Biphenyl Ligroin Iodine Methanol Ethanol Triphenylmethanol C6H5Br 24.31 C6H5CO2C2H5 C2H5OC2H5 74.12 98.07 84.01 142.04 84.93 (C6H5)2 (high bp pet. ether) alkane mixt. 253.8 CH3OH C2H5OH (C6H5)3COH 32.04 46.07 154.21 2.159 2.68 1.325 0.992 0.656 4.930 0.7914 0.7893 133 -94 -117 65 78.5 -95.1 71 40.1 255.9 60-80 270 0.7138 -116 34.5 1.75 649 1090 56 CHEM360 Report Book 2005-06 Exp.16 SAMPLE EXPERIMENT 16 FLOW CHART Part A REAGENT PROCEDURE / STEP Dry all glassware OBSERVATION ___g Mg (s) ___ mL diethyl ether ___ mol bromobenzene ___ mL diethyl ether Keep warm and reflux for a further 20-30 min. Proceed to Part B 57 Exp.16 CHEM360 Report Book 2005-06 SAMPLE EXPERIMENT 16 FLOW CHART Part B and C REAGENT PROCEDURE / STEP OBSERVATION 58 CHEM360 Report Book 2005-06 Exp.16 Experiment 16 Results: Table 2. Summary Table of Observations: Procedural Step Comment or Observation Table 3. Table of Product Data for Triphenylmethanol, the Grignard Reaction Product. Table 3. presents the summary of the results of the experiment. The calculations for limiting reagent, theoretical yield and percent yield are shown below the table. Note: _________________ was found to be the limiting reagent. Product Name Yield Appearance Observed Lit. Melting Theoretical % Yield (Mass in g) of Solid Melting Pt.* Pt. Yield (g) (C) (C) *uncalibrated thermometer used. Limiting Reagent and Theoretical Yield Calculation: Moles of magnesium used in the reaction = Moles of bromobenzene used in the reaction = Moles of ethyl benzoate used in the reaction = Theoretical Yield of triphenylmethanol = % Yield Calculation: 59 Exp.16 CHEM360 Report Book 2005-06 Fig 1. TLC Analysis of Biphenyl, Mother Liquor, Crude and Recrystallized Triphenylmethanol Lane# Dist to Center Spot ( ) Dist to Solvent Front ( ) Rf 60 CHEM360 Report Book 2005-06 Exp.16 Discussion: Comments on and reasons for yield (high/med/low), purity (high/med/low), sources of error, etc.: Structure of Product Conclusion: 61 Exp.16 CHEM360 Report Book 2005-06 Experiment 16 Questions: 1. How do you account for the fact that biphenyl is formed as a by-product in this reaction? 2. Why do you think that reactions involving Grignard reagents are sometimes carried out in an atmosphere of nitrogen or argon? 3. A Grignard reaction was performed and the following 1H-NMR (90 MHz in CDCl3) was obtained of the purified product. Deduce the product's structure (Molecular Formula = C7H6O2). Also write the overall reaction for its formation from any organohalide and carbonyl compound. 1 H-NMR Spectral Data: Shift 7.5 8.1 12.1 Signal # 1 2 3 Integrat'n 3H 2H 1H Splitting Comment #Neighbour H Signal Assignment Xchngs with D2O 62 CHEM360 Report Book 2005-06 Exp.17 CHEM360 Experiment 17 Report Student Name:___________________ Experiment 17 Prelab Questions 1. In Part C, the oxidizing agent is: Date:___________ ID Number:___________ 2. In Part D, the 4-acetamidobenzoic acid is hydrolyzed by the addition of _________? What is hydrolyzed i.e., what is removed from the starting reagent to form the product? 3. In Part E, what is the purpose of the 100% ethanol used in Step 2. 4. During a reflux, what constant states are maintained while the reaction proceeds? (there are 3) 5. If you obtained % yields of 85%, 65% and 90% in a three-step synthesis, what is the overall % yield? 63 Exp.17 CHEM360 Report Book 2005-06 CHEM360 Experiment 17 Report Student Name:___________________ Title: Objective(s): Date:___________ ID Number:___________ Reaction equation(s): Introduction: 64 CHEM360 Report Book 2005-06 Exp.17 Introduction (cont.): 65 Exp.17 CHEM360 Report Book 2005-06 Procedure: (Ref: ) Changes/Modification: Part C. Procedure for the synthesis of 4-acetamidobenzoic acid. Procedural Step Record amount/appearance of pure 4-methylacetanilide used Reaction/Equipment Setup Reaction Observations/Comments/Inferences Reaction Work-up Part D. Procedure for the synthesis of 4-aminobenzoic acid. Procedural Step Record amount of pure 4-acetamidobenzoic acid used Reaction/Equipment Setup Reaction Observations/Comments/Inferences Reaction Work-up Part E. Procedure for the synthesis of benzocaine. Procedural Step Record amount/appearance of pure p-aminobenzoic acid used Reaction/Equipment Setup Reaction Observations/Comments/Inferences Reaction Work-up 66 CHEM360 Report Book 2005-06 Exp.17 Table 1. Table of Reagents for Experiment 17 Reagent Formula Mwt. d mp bp Haz. Properties 4-methylacetanilide magnesium sulfate -7H2O potassium permanganate sodium hydrogen sulfite 4-acetamidobenzoic acid hydrochloric acid Ammonia (conc.) acetic acid, glacial 4-aminobenzoic acid Ethanol sulfuric acid sodium carbonate ethyl-4-aminobenzoate H2SO4 Na2CO3 HCl NH3 MgSO4 -7H2O KMnO4 NaHSO3 67 Exp.17 SAMPLE EXPERIMENT 17 FLOW CHART Part C REAGENT PROCEDURE / STEP CHEM360 Report Book 2005-06 OBSERVATION 68 CHEM360 Report Book 2005-06 SAMPLE EXPERIMENT 17 FLOW CHART Part D REAGENT PROCEDURE / STEP Exp.17 OBSERVATION 69 Exp.17 SAMPLE EXPERIMENT 17 FLOW CHART Part E REAGENT PROCEDURE / STEP CHEM360 Report Book 2005-06 OBSERVATION 70 CHEM360 Report Book 2005-06 Exp.17 Experiment 17 Results: Table 2. Table Summarizing Observations: Procedural Step Observations/Comments/Inferences Table 3.1 Properties of the 4-methylacetanilide Oxidation Product, 4-acetamidobenzoic acid Table 3.1 shows a summary of the results of the 4-acetamidobenzoic acid synthesis. The calculations for theoretical yield and percent yield are shown below the table. Note: _________________ was the limiting reagent, since the only other reagent involved in the reaction, potassium permanganate was added in excess. Name of Product Mass (g) Appearance of Solid Melting Pt. (C) Theoretical Yield (g) % Yield Theoretical Yield Calculation: % Yield Calculation: 71 Exp.17 CHEM360 Report Book 2005-06 Table 3.2 Properties of the 4-methylacetanilide Oxidation Product, 4-aminobenzoic acid Table 3.2 shows a summary of the results of the 4-aminobenzoic acid synthesis. The calculations for theoretical yield and percent yield are shown below the table. Note: ___________ was the limiting reagent, since the only other reagent involved in the reaction, phosphoric acid, served as a catalyst. Name of Product Mass (g) Appearance of Solid Melting Pt. (C) Theoretical Yield (g) % Yield Theoretical Yield Calculation: % Yield Calculation: 72 CHEM360 Report Book 2005-06 Table 3.3 Properties of Fisher Esterification Product, benzocaine Exp.17 Table 3.3 shows a summary of the results of the benzocaine synthesis. The calculations for theoretical yield and percent yield are shown below the table. Note: ___________ was the limiting reagent, since the only other reagent involved in the reaction, phosphoric acid, served as a catalyst. Mass (g) Appearance of Solid Melting Pt. (C) Theoretical Yield (g) % Yield Theoretical Yield Calculation: % Yield Calculation: (Theoretical) Overall % Yield Calculation 73 Exp.17 CHEM360 Report Book 2005-06 Table 4.1 Tabulation of Characteristic Infrared and 1H-NMR Absorptions for 4-acetamidobenzoic acid. Infrared Data: Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated > 3000 cm-1 Between 3000 and 2000 cm-1 Between 2000 and 1400 cm-1 < 1400 cm-1 Functional Group(s) absent: 1 H-NMR Data: Signal # Shift Integrat'n Splitting Comment #Neighbour H Signal Assignment Table 4.2 Tabulation of Characteristic Infrared and 1H -NMR Absorptions for 4-aminobenzoic acid. Infrared Data: Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Functional Group Indicated > 3000 cm-1 Between 3000 and 2000 cm-1 Between 2000 and 1400 cm-1 < 1400 cm-1 Functional Group(s) absent: 1 H-NMR Data: Signal # Shift Integrat'n Splitting Comment #Neighbour H Signal Assignment 74 CHEM360 Report Book 2005-06 Table 4.3 Tabulation of Characteristic Infrared and 1H -NMR Absorptions for benzocaine. Infrared Data: Absorption Band# Wavenumber (cm-1) Peak Shape (sharp, broad) Peak Intensity (strong, med. or weak) Exp.17 Functional Group Indicated > 3000 cm-1 Between 3000 and 2000 cm-1 Between 2000 and 1400 cm-1 < 1400 cm-1 Functional Group(s) absent: 1 H-NMR Data: Shift Signal # Integrat'n Splitting Comment #Neighbour H Signal Assignment 75 Exp.17 CHEM360 Report Book 2005-06 Discussion: Comments on and reasons for yield (high or low), purity (high/med/low), sources of error, overall synthesis effectiveness, etc. Conclusion: Structure of Product 76 CHEM360 Report Book 2005-06 Exp.17 Experiment 17 Questions: 1. In Step 6 Part A, what is the purpose of adding sodium hydroxide to the reaction mixture? 2. In the discussion pertaining to the hydrolysis of 4-acetamidobenzoic acid, it was argued that the presence of the electron-withdrawing carboxyl group in the para position could result in the occurrence of some nucleophilic displacement if the hydrolysis was carried out under acidic conditions and an elevated temperature. What would the product of such a nucleophilic displacement reaction? 3. Write the balanced equation for the oxidation of 4-methylacetanilide to 4acetamidobenzoic acid as carried out in Part C of the synthesis. 4. Write the mechanism for the reaction of 4-methylaniline with acetic anhydride. What was the purpose of adding sodium acetate to the reaction mixture when you performed this acetylation in Part B of the synthesis? 77 Table of Reagents Compound Name acetanilide acetanilide,4-methyl acetanilide, p-nitro acetanilide, o-nitro acetanilide, m-nitro acetic acid, glacial (17.4 M) acetic acid, p-ethoxyphenyl acetic anhydride acetone acetone, diethylamino acetophenone activated carbon allyl alcohol (2-propen-1-ol) ammonia (14.8 M) ammonium hydroxide (14.8 M) aniline aniline, 4-bromo aniline, 4-chloro aniline, o-ethyl aniline, 2-ethoxy aniline, 4-methyl aniline, 3-nitro aspirin (see salicylic acid, acetate) benzaldehyde benzaldehyde, 4-methyl benzaldehyde,4-methoxy benzaldehyde, 4-nitro benzene benzene, bromo benzene, chloro benzoate, ethyl benzoate, methyl benzocaine, 4-aminobenzoic acid, ethyl ester, benzoic acid benzoic acid, 4-acetamido benzoic acid, 4-amino benzoic acid, 3-chloro benzoic acid, 4-chloro benzoic acid, 3-hydroxy benzoic acid, 4-hydroxy benzoic acid, 2-methyl benzoic acid, 4-methyl benzoic acid, 4-nitro benzonitrile benzophenone benzoyl chloride benzyl alcohol benzyl amine benzyl chloride biphenyl boric acid Bradys Reagent bromine butanal Chemical Formula CH3CONHC6H5 CH3CONHC6H4CH3 CH3CONHC6H4NO2 CH3CONHC6H4NO2 CH3CONHC6H4NO2 CH3CO2H C2H5OC6H4CH2CO2H (CH3CO)2O CH3COCH3 (C2H5)2NCH2COCH3 C6H5COCH3 CH2=CHCH2OH NH3 NH4OH C6H5NH2 BrC6H4NH2 ClC6H4NH2 CH3CH2C6H4NH2 CH3CH2OC6H4NH2 CH3C6H4NH2 NO2C6H4NH2 CH3CO2C6H4CO2H C6H5CHO CH3C6H4CHO CH3OC6H4CHO NO2C6H4CHO C6H6 C6H5Br C6H5Cl C6H5CO2C2H5 C6H5CO2CH3 H2NC6H4CO2C2H5 C6H5CO2H CH3CONHC6H4CO2H H2NC6H4CO2H ClC6H4CO2H ClC6H4CO2H HOC6H4CO2H HOC6H4CO2H CH3C6H4CO2H CH3C6H4CO2H O2NC6H4CO2H C6H5CN (C6H5)2CO C6H5COCl C6H5CH2OH C6H5CH2NH2 C6H5CH2Cl C6H5C6H5 H3BO3 (NO2)2C6H3NHNH2 Br2 CH3CH2CH2CHO Solid (S) or Liquid (L) S S S S S L S L L L L S L L L L S S L L L S S L L L S L L L L L S S S S S S S S S S S L S L L L L S S L L L Formula Weight 135.17 149.19 180.16 180.16 180.16 60.05 180.2 102.09 58.08 129.2 120.15 58.08 17.03 35.05 93.13 172.03 127.57 121.18 137.18 107.16 138.13 180.16 106.12 120.15 136.15 151.12 81.14 157.02 112.56 150.18 136.15 165.19 122.12 179.18 137.14 156.57 156.57 138.12 138.12 136.15 136.15 167.12 103.12 182.22 140.57 108.14 107.16 126.59 154.21 61.83 CHEM360 Report Book 2005-06 MP or BP (C) 113-115 149-151 216 94 154-156 118.1 87-90 140 56.5 64/16mm 202 96-98 Density (g/mL) Refract. Index Hazardous Properties* Toxic, irritant Irritant Irritant Irritant Irritant Corrosive, hygroscopic Irritant Corrosive, lachrymator Flammable, irritant Irritant Irritant (see charcoal) Highly Toxic, flammable Corrosive, lachrymator Corrosive, lachrymator Highly toxic, irritant Toxic, irritant Highly toxic, irritant Toxic, irritant Irritant, light sens. Toxic, irritant Highly toxic, irritant Irritant, toxic Hi.toxic, cancer susp.agent Irritant (p-tolualdehyde) Irritant, (anisaldehyde) Irritant Flamm., cancer susp.agent Irritant Flammable, irritant Irritant Irritant Irritant Irritant Irritant Irritant Irritant Irritant Irritant Irritant See also o-toluic acid See also p-toluic acid Irritant Irritant Irritant Corrosive, toxic Irritant, hygroscopic Corrosive, lachrymator Hi.toxic, cancer susp.agent Irritant Irritant, hygroscopic Highly toxic, oxidizer Flammable, corrosive 1.419 1.049 1.082 0.7899 0.832 1.030 0.854 0.90 0.90 1.022 1.3900 1.3590 1.4250 1.5325 1.4120 184 62-64 72.5 210 231-233 196 114 138-140 179.5 204-205 248 106 80.1 155-156 132 212.6 198-199 88-92 122.4 256.5 188-189 158 243 210-203 215-217 103-105 180-182 239-241 191 49-51 198 205 184-185 179 69-71 1.5860 1.051 0.989 1.5590 1.5550 1.5700 1.044 1.019 1.119 0.908 1.491 1.107 1.051 1.094 1.5450 1.5454 1.5730 1.4990 1.5590 1.5240 1.5050 1.5170 1.374 1.010 1.5280 1.211 1.5530 1.045 1.5400 0.981 1.5430 1.1002 0.992 1.435 See hydrazine, 2,4-dinitrophenyl 159.82 58.8 3.102 72.11 75 78 CHEM360 2005-06 Table of Reagents Compound Name 1,3-butadiene, E,E-1,4-diphenyl butane, 1-bromo butane, 2-bromo butane, 1-chloro butane, 2-chloro 1-butanol 1-butanol, 3-methyl 2-butanol 2-butanone 2-butanone, 3-hydroxy-3-methyl 1-butene, 3-chloro3-buten-2-ol n-butyl butyrate butyric acid 3-butyn-2-ol, 2-methyl calcium carbonate calcium chloride, anhydr. camphor (1R, +) carbon dioxide, solid carbon tetrachloride charcoal (Norit) chloroform cinnamaldehyde, trans cinnamic acid, trans crotonaldehyde Cyclohexane cyclohexane, bromo cyclohexane, methyl cyclohexene cyclohexanol cyclohexanone cyclohexanone, 4-methyl cyclopentane cyclopentane, bromo cyclopentanone dichloromethane diethyl ether (see ethyl ether) 1,4-dioxane diphenylmethanol ethyl acetate ethyl alcohol, anhydrous ethyl ether, absolute fluorene formaldehyde (soln) formamide, N,N-dimethyl furfuryl amine gold n-hexane hydrazine, 2,4-dinitrophenyl hexanes hydrochloric acid, conc. 12 M Chemical Formula C6H5C4H4C6H5 CH3CH2CH2CH2Br CH3CH2CHBrCH3 CH3CH2CH2CH2Cl CH3CH2CHClCH3 CH3CH2CH2CH2OH (CH3)2CH(CH2)2OH CH3CH2CHOHCH3 CH3CH2COCH3 (CH3)2C(OH)COCH3 CH3CH(Cl)CH=CH2 CH2=CHCH(OH)CH3 C3H7CO2C4H9 CH3(CH2)2CO2H CHCC(CH3)2OH CaCO3 CaCl2 C10H16O CO2 CCl4 CHCl3 C6H5CH=CHCHO C6H5CH=CHCO2H CH3CH=CHCHO C6H12 C6H11Br C6H11CH3 C6H10 C6H11OH C6H10(=O) CH3C6H9(=O) C5H10 C5H9Br C5H8(=O) CH2Cl2 C2H5OC2H5 C4H8O2 (C6H5)2CH(OH) CH3CO2C2H5 CH3CH2OH CH3CH2OCH2CH3 C13H10 HCHO HCON(CH3)2 (C4H3O)CH2NH2 Au CH3(CH2)4CH3 (NO2)2C6H3NHNH2 C6H14 HCl Solid (S) or Liquid (L) S L L L L L L L L L L L L L L S S S S L S L L S L L L L L L L L L L L L L L S L L L S L L L S L 70% soln L L Formula MP or BP Density Refract. Weight (g/mL) Index (C) 206.29 153 137.03 101.3 1.276 1.4390 137.03 91.3 1.255 1.4369 92.57 78.4 0.886 1.4024 92.57 68.2 0.873 1.3960 74.12 117-118 0.810 1.3990 88.15 130 0.8092 1.4053 74.12 99.5-100 0.807 1.3970 72.11 80 0.805 1.3790 102.13 140-141 0.971 1.4150 90.55 62-65 0.900 1.4155 72.11 96-97 0.832 1.4150 144.21 164-165 0.871 1.4060 88.11 165.5 0.9577 1.3980 84.12 104 0.868 1.4200 100.09 2.930 110.99 2.150 152.24 179-181 0.990 1.5462 44.01 -78.5(subl.) 153.82 76 1.594 Decolourizing agent, used in recrystallizations 119.38 61.3 1.500 132.16 246(decomp) 1.048 1.6220 148.16 135-136 70.09 102.4 0.846 1.4365 84.16 80.7 0.779 1.4260 163.06 166.2 1.324 1.4950 98.19 101 0.770 1.4220 82.15 83 0.811 1.4460 100.16 161.1 0.963 1.4650 98.15 155.6 0.947 1.4500 112.17 170 0.914 1.4460 70.14 49.5 0.751 1.4000 149.04 137-138 1.390 1.4881 84.12 130.6 0.951 1.4370 84.93 40.1 1.325 1.4240 74.12 34.6 0.708 1.3530 88.11 100-102 1.034 1.4220 184.24 65-67 88.11 76-77 0.902 1.3720 46.07 78.5 0.785 1.3600 74.12 34.6 0.708 1.3530 166.22 114-116 30.03 96 1.083 1.3765 73.10 149-156 0.9487 1.4310 97.12 145-146 1.099 1.4900 196.97 1064 19.28 86.18 69 0.659 1.3750 198.14 86.18 68-70 0.672 1.3790 36.46 1.20 Hazardous Properties* Irritant Flammable, irritant Flammable, irritant Flammable liquid Flammable liquid Flammable, irritant Irritant Flammable, irritant Flammable, irritant Irritant Flammable, lachrymator Flammable, irritant Irritant Corrosive, toxic Flammable, toxic Irritant, hygroscopic Irritant, hygroscopic Flamm., irritant Frost bite burns Susp. Cancer agent Irritant Highly toxic Irritant Irritant Highly toxic, flammab. Flammable, irritant Flammable, irritant Flammable, irritant Flammable, irritant Irritant, hygroscopic Corrosive, toxic Corrosive, toxic Flammable, irritant Flammable Flammable, irritant Toxic, irritant Flammable, toxic Flamm., cancer susp.agent Irritant Flammable, irritant Flammable, poison Flammable, irritant Irritant suspect. Cancer agent suspect. Cancer agent Irritant Expensive/valuable Flammable, irritant Flammable, irritant Flammable, irritant Corrosive, highly toxic 79 Table of Reagents CHEM360 Report Book 2005-06 Compound Name iodine isoamyl acetate (isopentyl acetate) isoamyl alcohol isopentyl alcohol lichen ligroin (high bp petrol. Ether) Lucas Reagent magnesium (metal) magnesium oxide magnesium sulfate, anhydrous magnesium sulfate, 7-hydrate manganese dioxide methanol, anhyd. methanol, diphenyl methanol, triphenyl methylene chloride mineral spirits (light kerosene) naphthalene nitric acid (conc. 15.4 M) 2-octanone pentane 3-pentanol 3-penten-2-one, 4-methyl petroleum ether, (Skelly B) petroleum ether, hi bp (ligroin) phenethyl alcohol phenol phenol, 2,4-dimethyl phenol, 2,5-dimethyl phenylacetylene phenylmagnesium bromide phosphoric acid (85%, 14.7 M) potassium chromate potassium dichromate potassium hydroxide potassium iodide potassium permanganate propane, 2-chloro, 2-methyl propane, 2-nitro propanoic acid (or propionic acid) 1-propanol 1-propanol, 2-methyl2-propanol, 2-methylpropionate, ethyl propionic acid rosaniline hydrochloride salicylic acid salicylic acid, acetate ester Schiffs Reagent silane, tetramethyl silica, sand silver nitrate sodium acetate sodium acetate, trihydrate Chemical Formula I2 CH3CO2C5H11 (CH3)2CH(CH2)2OH (CH3)2CH(CH2)2OH C6-C7 (light naphtha) Mg MgO MgSO4 MgSO4.7H2O MnO2 CH3OH (C6H5)2CH(OH) (C6H5)3C(OH) CH2Cl2 C12-C14 C10H8 HNO3 CH3(CH2)5COCH3 C5H12 C2H5CH(OH)C2H5 (CH3)2C=CHCOCH3 Mixt. Of C5-C6 Mixt. Of C6-C7 C6H5CH2CH2OH C6H5OH (CH3)2C6H3OH (CH3)2C6H3OH C6H5CCH C6H5MgBr H3PO4 K2CrO4 K2Cr2O7 KOH KI KMnO4 (CH3)3CCl (CH3)2CHNO2 CH3CH2CO2H CH3CH2CH2OH (CH3)2CHCH2OH (CH3)3COH C2H5CO2C2H5 C2H5CO2H C20H14(NH2)3Cl HOC6H4CO2H CH3CO2C6H4CO2H Si(CH3)4 SiO2 AgNO3 CH3CO2Na CH3CO2Na 3H2O Solid (S) or Formula MP or BP Density Refract. Liquid (L) Weight (g/mL) Index (C) S 253.81 133 4.930 L 130.19 142 0.8670 1.4000 L L S L 60-80 0.656 1.3760 Solution of hydrochloric acid/zinc chloride (from zinc dust) S 24.31 651 1.75 S 40.31 3.58 S 120.37 2.660 S 246.48 1.670 S 86.94 535 (dec.) 5.026 L 32.04 64.5 0.791 1.3290 S 184.24 69 S 260.34 164.3 L 84.93 40.1 1.325 1.4230 L 179-210 0.752 1.4240 S 128.17 80.5 L 63.01 1.400 L 128.22 173 0.819 1.4150 L 72.15 36.1 0.626 1.3580 L 88.15 115/749mm 0.815 1.4100 L 98.15 129 0.858 1.4450 L 35-60 0.640 L 60-80 0.656 1.3760 L 122.17 221/750mm 1.023 1.5320 S 94.11 40-42 1.071 S 122.17 22-23 1.011 1.5380 S 122.17 75-77 0.971 L 102.14 142-144 0.930 1.5490 L 181.33 1.134 L 98.00 1.685 S 194.20 968 2.732 S 294.19 398 S 56.11 S 166.01 681 3.130 S 158.04 d<240 2.703 L 92.57 50 0.851 1.3848 L 89.09 120 0.992 1.3940 L 74.08 141 0.9930 1.3869 L 60.11 97.4 0.8035 1.3850 L 74.12 108.1 0.8018 1.3955 L 74.12 82.3 0.7887 L 102.13 99 0.891 1.3840 L 74.08 141 0.993 1.3860 Solution 337.86 250 (dec) S 138.12 158-160 S 180.16 138-140 Solution of roseaniline hydrochloride & sulfur dioxide L 88.23 26-28 0.648 1.3580 S 60.09 NA S 169.88 212 4.352 S 82.03 S 136.08 58 1.45 Hazardous Properties* Corrosive, highly toxic Flammable, irritant (see 1-butanol, 3-methyl-) (see 1-butanol, 3-methyl-) Allergin Flammable, irritant Toxic, irritant Flammable Moist. Sens., irritant Hygroscopic ( psom salt) Oxidizer, irritant High. Toxic, flammable Irritant Irritant See dichlormethane Flammable, irritant Flamm., susp.cancer agent Corrosive, oxidizer Irritant Flammable, irritant Flammable, irritant Flammable, lachrymator Flammable, toxic Flammable, toxic Toxic, irritant Highly toxic, corrosive Corrosive, toxic Corrosive, toxic Flamm., cancer susp.agent Flammable, moist.sensit. Corrosive Canc.susp.agent, oxidizer Hi.toxic, canc.susp.agent Corrosive, toxic Moist.sens., irritant Oxidizer, corrosive Flammable Canc.susp.agent, flamm. Corrosive, toxic Flammable, irritant Flammable, irritant Flammable, irritant Flammable, irritant Corrosive, toxic Susp. cancer agent Toxic, irritant Irritant, toxic Toxic Flammable, hygroscopic abrasive Highly toxic, oxidizer hygroscopic Hygroscopic 80 CHEM360 2005-06 Table of Reagents Compound Chemical Solid (S) or Formula MP or BP Density Name Formula Liquid (L) Weight (g/mL) (C) sodium bisulfite NaHSO3 S 1.480 sodium borohydride NaBH4 S 37.38 400 sodium bicarbonate NaHCO3 S 84.01 2.159 sodium carbonate Na2CO3 S 105.99 851 2.532 sodium chloride NaCl S 58.44 801 2.165 sodium dichromate, dihydrate Na2Cr2O7.2H2O S 298.00 2.350 sodium hydrogen carbonate NaHCO3 S 84.01 2.159 sodium hydroxide NaOH S 40.00 sodium iodide NaI S 149.89 661 3.670 sodium metabisulfite Na2S2O5 S 190.10 1.480 sodium methoxide NaOCH3 S 54.02 sodium sulfate Na2SO4 S 142.04 884 2.680 styrene C6H5CH=CH2 L 104.15 146 0.909 C6H5CH=CHBr L 183.05 112/20mm 1.427 styrene, -bromo sucrose C12H22O11 S 342.30 185-187 1.5805 sulfur dioxide SO2 Gas 64.06 -10 bp H2SO4 L 98.08 1.840 sulfuric acid (conc. 18 M) sulfurous acid H2SO3 L 82.08 1.030 L-tartaric acid HO2CC2H2(OH)2CO2H S 150.09 171-174 tetrahydrofuran C4H8O L 72.11 65-67 0.889 tetramethylsilane Si(CH3)4 L 88.23 26-28 0.648 tin Sn S 118.69 7.310 Tollens Reagent L See ammonia + silver nitrate toluene C6H5CH3 L 92.14 110.6 0.867 toluene, 4-nitro NO2C6H4CH3 S 137.14 52-54 1.392 o- or 2-toluic acid CH3C6H4CO2H S 136.15 103-105 p- or 4-toluic acid CH3C6H4CO2H S 136.15 180-182 triethylphosphite (C2H5O)3P L 166.16 156 0.969 triphenylmethanol (C6H5)3C(OH) S 260.34 164.3 NH2CONH2 S 60.06 135 1.335 urea (-) usnic acid C18H16O7 S 344.32 198 (+) usnic acid C18H16O7 S 344.32 201-203 H2O L 18.02 100 water water, ice H2O S/L 18.02 0 1.00 xylenes CH3C6H4CH3 L 106.17 137-144 0.860 zinc, dust Zn S 65.37 419.5 zinc chloride, anhydrous ZnCl2 S 136.28 283 2.91 *Be sure to consult the chemicals MSDS for more specific detail on hazardous properties. Refract. Index 1.6070 1.4070 1.3580 Hazardous Properties* Severe irritant Flam. solid, corrosive Moist. sensitive Irritant, hygroscopic Irritant, hygroscopic Hi.toxic, cancer susp.agent See sodium bicarbonate Corrosive, toxic Moist.sens., irritant Moist.sens., toxic Flam. solid, corrosive Irritant, hygroscopic Flammable Irritant Tooth Decay! Nonflamm, corrosive Corrosive, oxidizer Corrosive, toxic Irritant Flammable, irritant Flammable, hygroscopic Flammable solid, moist.sens. Flammable, toxic Hi.toxic, irritant Probable irritant Probable irritant Moist. sens., irritant Probable irritant Irritant Toxic Toxic Will burn skin when hot Frostbite, hypothermia Flammable, irritant Flammable, moist.sens. Corrosive, toxic 1.4960 1.4130 1.33 1.4970 81 Questionnaire CHEM360 Report Book 2005-06 Organic Chemistry II Chemistry 360 Laboratory Course Questionnaire Lab Session Type (circle): Weekend or Weeklong The Centre for Natural and Human Science would appreciate your confidential help in improving our laboratory program. Please complete the following questionnaire by circling one of the following responses on a scale of 1-5: Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) Submit the completed questionnaire by mail to the Science Lab Coordinator at: Centre for Science, 1University Drive, Athabasca University, Athabasca, AB, T9S 3A3. Please rate the Lab Instructor(s) in the items specified below: 1. The lab instructor was competent and made the experiments interesting and instructional. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) The instructor presented an overview of the laboratory exercise in an interesting and helpful manner, pointing out likely problems in the lab procedure at the start of the experiment and stressing safety precautions. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) The lab instructor speaks clearly and understandably. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), 2. 3. Strongly Disagree (1) 4. The lab instructor circulates through the lab during the experiments and actively monitors our work. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) The instructor treated me with respect. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Overall, my instructor was effective. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), 5. Strongly Disagree (1) 6. Strongly Disagree (1) Please rate the Lab Course in the items specified below by circling the appropriate number or letter: 7. The CHEM360 Laboratory Manual was easy to read and understandable. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) The CHEM360 Laboratory Report Book was easy to read and understandable. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) Working on the procedure and table of reagents in the CHEM360 Report Book before coming to the lab helped me understand what to do in the laboratory and what the dangers are in each experiment. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) 8. 9. 10. The information required to answer the pre-lab questions in the CHEM360 Report Book was easy to find. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) 11. I found the whole CHEM360 lab session very rushed and poorly organized. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) 12. Recording my results was made easy by the prepared/formatted tables in the results section. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) 82 CHEM360 2005-06 Questionnaire Organic Chemistry II Chemistry 360 Laboratory Course Questionnaire (cont.) 13. Which experiment did you enjoy the most? a) Fisher Esterification b) Functional Group Tests for Alcohols and Alkyl/aryl halides c) Reduction of ketone d) Aldol Condensation f) Functional Group Tests for Aldehydes and Ketones e) 1H-NMR Tutorial g) Grignard Reaction h) Benzocaine Synthesis Which experiment did you like the least? a) Fisher Esterification b) Functional Group Tests for Alcohols and Alkyl/aryl halides c) Reduction of ketone d) Aldol Condensation f) Functional Group Tests for Aldehydes and Ketones e) 1H-NMR Tutorial g) Grignard Reaction h) Benzocaine Synthesis From which experiment did you learn the most? a) Fisher Esterification b) Functional Group Tests for Alcohols and Alkyl/aryl halides c) Reduction of ketone d) Aldol Condensation f) Functional Group Tests for Aldehydes and Ketones e) 1H-NMR Tutorial g) Grignard Reaction h) Benzocaine Synthesis From which experiment did you learn the least? a) Fisher Esterification b) Functional Group Tests for Alcohols and Alkyl/aryl halides c) Reduction of ketone d) Aldol Condensation f) Functional Group Tests for Aldehydes and Ketones e) 1H-NMR Tutorial g) Grignard Reaction h) Benzocaine Synthesis Working on an experiment with a lab partner improved my understanding of the experiment and overall knowledge of organic chemistry. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) 14. 15. 16. 17. 18. I had many questions that went unanswered while I was in the lab. Strongly agree (1), Agree (2), Neutral (3), Disagree (4), Strongly Disagree (5) 19. I would recommend to a friend to take Athabasca University's organic chemistry course. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) 20. Overall, the laboratory component is a valuable part of AU's organic chemistry course. Strongly agree (5), Agree (4), Neutral (3), Disagree (2), Strongly Disagree (1) Do you have any other comments to add about your instructor(s) or this CHEM360 laboratory course? 83

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CANCUNS PREMIER CHARTER SERVICE SINCE 1993WAVE RIDER ADVENTURES ON THE MAYAN RIVIERAR SAILING EXCURSIONS R SNORKELING &amp; SCUBA DIVING R DEEP SEA FISHING R TOURS OF HISTORIC COZUMEL R LUXURIOUS 50 FOOT YACHT R PROFESSIONAL CREWTHE CANCUN LADYPR
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CREATING YOUR FIRST HTML DOCUMENT THE BASIC STEPS IN CREATING AND EDITING HTML DOCUMENTS 1) Create the basic code using WordPad or Notepad and save as *.htm in plain text format. 2) Open the *.htm page in your browser 3) Switch back to the code docum
Athens Tech - COMP - 210
2015PLAYADESDELPHINESAVE CANCUN,QR,MEXICO 34765 PH:838723 EMAILwaverider@mayanet.com WWWhttp:/cancunlady.comEduardoMontoya BusinessLoansManager, FirstNationalBankofMexico, 4321BlvdCaracol, ZonaHoteleria, Cancun,Q.R. DearSir;Saturday,March13,1998
Athens Tech - COMP - 210
ADVENTURE,EXCITEMENTAND STUNNINGBEAUTYEnjoyadayofmatchlessadventureon ourbeautiful50footTempestsailing yachttheCancunLady. Ourexperiencedandprofessional guides,instructorsandcrewwillensure thatyouhaveanexcitingandtruly memorabledayenjoyingthebeautif
Athens Tech - BIOL - 205
Tutor-marked Assignment #1: Version AChapters 22-30InstructionsThis version is to be done by students whose last names begin with the letters A-M. Answer the following questions, and submit your answers to your tutor for evaluation. Attach a Tutor
Athens Tech - BIOL - 235
Course AnnouncementBiology 235 Human Anatomy &amp; PhysiologyPlease make a note of the following amendment to the Course TextbookCourse TextbookA two-tone green insert titled eGrade Plus (Wiley PLUS) was included with the course textbook.Using e
Athens Tech - ENGL - 491
A Very Short History of CyberpunkMarcus Janni PivatoMany people seem to think that William Gibson invented The cyberpunk genre in 1984, but in fact the cyberpunk aesthetic was alive well before Neuromancer (1984). For example, in my opinion, Ridle
Athens Tech - MATH - 101
Math 101NOTES ON INVERSES OF FUNCTIONSHere is a brief discussion on inverses of functions that are covered in Unit 1 of the Math 101 Study Guide.Definition of the Inverse of a Function The inverse of a function f is another function, generally de
Athens Tech - MATH - 101
Math 101THE FACTOR THEOREMTaking a Closer Look at the Factor Theorem Recall from page 100 of the Study Guide, Unit 3: The Factor Theorem states the following: For a polynomial P of degree n (a positive non-zero integer), P(a) = 0 where a is any rea
Athens Tech - MATH - 101
Math 101NOTES ON TRANSFORMATIONS OF FUNCTIONSHere is a compendium of the various transformations of functions that are covered in Math 101 with some additional explanations on horizontal shifts, stretches and contractions. RIGID TRANSFORMATIONS Ver
Athens Tech - ENGL - 324
Marriage in Othello and Macbeth By Tom Wolfe Othello and Macbeth are both characters who make a tenuous effort at determining their own fortune. This is symbolised in the case of Othello by his marriage to Desdemona, and in the case of Macbeth by his
Athens Tech - ENGL - 423
Postcolonialism and First Nations in Canada by Quentin Kayne This essay will look at postcolonial literary theory in an aboriginal Canadian context. The arguments of three major postcolonial theorists, Edward Said, Homi Bhabha and Gayatri Chakravorty
Athens Tech - ENGL - 324
Ernstberger 1Henry IV Part One: Explication By Wanda ErnstbergerKing Henry IV and Prince Hal deliver the lines How bloodily the sun begins. the unborn times? (5.1.121) just before the battle with Hotspur and the rebel army. The scene opens with a
Athens Tech - ENGL - 492
Buccella,LisaMarie StudentNo.2532500Whats the Difference? The Politics of Difference in Feminist Representation Lisa Marie BuccellaIntroduction The politics of difference in feminist theory is hardly a new phenomenon. Feminism has been largely ce
Athens Tech - ENGL - 492
Postcolonialism and First Nations in Canada by Quentin Kayne This essay will look at postcolonial literary theory in an aboriginal Canadian context. The arguments of three major postcolonial theorists, Edward Said, Homi Bhabha and Gayatri Chakravorty
Athens Tech - ENGL - 304
Course AnnouncementEnglish 304 A History of Drama: Part II: Modernist TheatrePlease note the following amendment to the Student ManualStudent ManualCourse Materials The course anthology, The Harcourt Brace Anthology of Drama, 3rd ed. is out of
Athens Tech - ENGL - 381
Course AnnouncementEnglish 381 Creative Writing in ProsePlease make a note of the following amendment to the Study Guide Student ManualAs part of its evaluation components, English 381: Creative Writing in Prose now has an optional peer-to-peer
Athens Tech - ENGL - 303
Course AnnouncementEnglish 303 A History of Drama: Part I: Early StagesPlease note the following amendment to the Student ManualStudent ManualCourse Materials The course anthology, The Harcourt Brace Anthology of Drama, 3rd ed. is out of print,
Athens Tech - ENGL - 373
Course AnnouncementEnglish 373 Film and LiteraturePlease make a note of the following amendment to the Course Textbook Study GuideCourse TextbookTimothy Corrigan, A Short Guide to Writing about Film, exists in several editions which are very s
Athens Tech - ENGL - 373
Course AnnouncementEnglish 373: Film and LiteratureAs the film Vanya on 42nd Street is no longer available for inclusion in your course materials package, we now advise students to borrow a copy from the Athabasca University Library: (http:/library
UMass (Amherst) - COMP - 4190
74.419 Artificial IntelligenceCourse Introduction and ROASS DocumentInstructor &amp; Course Info Course Topics and approximate Schedule Assignments and Grade Breakdown The usual Stuff (including How to fail this course) Students introduce themselves
Athens Tech - ENGL - 305
Course AnnouncementEnglish 305 Literature for ChildrenPlease note the following amendments to the Study GuideDear Student, The publishers of three of the textbooks for English 305: Literature for Children have published new editions. This cours
UMass (Amherst) - COMP - 4190
74.419 Artificial Intelligence 2004Non-Classical LogicsNon-Classical Logics Specific Language Constructs added to classic FOPL Different Types of Logics Modal Logics most popular ones, e.g. Deontic Logic (allowed and forbidden; ethics; law)
UMass (Amherst) - COMP - 4190
74.419 Artificial Intelligence Knowledge RepresentationRussell and Norvig, Ch. 8Outline Ontological engineering Categories and objects Actions, situations and events Mental events and mental objects Reasoning systems for categories Reasoni
Athens Tech - ENGL - 324
Marriage in Othello and Macbeth By Tom WolfeOthello and Macbeth are both characters who make a tenuous effort at determining their own fortune. This is symbolised in the case of Othello by his marriage to Desdemona, and in the case of Macbeth by hi