Syllabus. Lab Text: Mohrig, Hammod and et al, Experimental Organic Chemistry (Macro and micro scale)

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1 Syllabus Chem 212- Organic Chemistry II Spring 2015 (2/8/16 6/616) Instructor: Dr. Chellappah Chanmugathas Lecture: 3 hrs per week M W 5:10-6:35 PM Room MSA 403 Lab: 6 hrs per week M W 6:40-9:55 PM Room: MSA 412 Office hours: M W 4:20-5:05 PM Room: MSA 412 Course description: Chemistry 212 is an organic chemistry course primarily for students who wish to continue in the fields of chemistry, pharmacy, medicine, dentistry etc This course is a continuation of Chem. 211, with emphasis on the remaining functional groups as well as special topics of molecular structure and reactions of organic compounds, bonding, stereochemistry, multi-step synthesis and application of modern instrumental and analytical methods. Introduction to the chemistry of some Biological compounds is also included. The laboratory work involves multi-step synthesis, structure determination, reaction mechanisms and qualitative analysis of Organic compounds. Chem. 212 provides the foundation for further work in Biochemistry. Prerequisites: A grade of C or better in Chemistry 211 is a prerequisite for enrollment in Chem Lecture Text: Solomons, Graham and Fryhle Craig, "Organic Chemistry 10 th Edition Lab Text: Mohrig, Hammod and et al, Experimental Organic Chemistry (Macro and micro scale) Optional Reading Materials: There is also a study guide for Solomons that has solutions to the problems. The following books are also suggested: (a) Organic Chemistry by Morrison and Boyd. (b) Organic Chemistry by Brown. (c) Organic Chemistry by Ege. (d) Organic Chemistry by McMurry. Please understand that you cannot learn by only attending classes, or by merely reading your notes or textbook. This course requires a lot of practicing in writing molecular structures, names of molecules, and reactions. There is no substitute for continuous effort to work out problems on your own. You should seek help only after you have done your best to solve the problem.

2 Chem 212 Dr. Chan Lecture: 5:10-6:35 Page 2 Spring 2016 chem212@gmail.com Lab: 6:40 9:55 I. Laboratory: Chemistry 212 is a laboratory course. Failure to perform the experiments and hand in the work on time will result in an unsatisfactory grade in the course. For reasons of safety, lab work must be done only during the assigned laboratory periods and in the presence of an instructor. NOTE: You must wear eye protection whenever you are in the lab. If you do not have the appropriate eye protection you may be dismissed from the laboratory section with loss of credit for that exercise. Do not wear contact glasses in the lab. They can absorb or trap some organic vapors and fumes and could cause eye damage. Eating or drinking in the lab is prohibited. Read the instructions and the procedure for the experiment before coming to the lab. Preparing flow charts before coming to the lab will help you to finish the experiment in time and prevents avoidable accidents from happening. Recommended Collateral Reading: Laboratory Techniques- Pavia, Lampman, and Kriz Additional Supplies: Safety Glasses - goggles or industrial quality safety glasses. Normal prescription glasses are not satisfactory. A duplicate page laboratory notebook. Reading Assignments: It is important to complete reading before class to maximize benefit from the laboratory work. Particular attention should be focused on experimental procedures and safety. Be sure that you have an understanding of the objective before you begin laboratory work. Prelab preparation and effective use of laboratory time: Laboratory time is limited. It is important to prepare carefully for the assigned experiment so as not to waste time. Furthermore, understanding the experimental procedures will enhance laboratory safety. An outline of the experimental procedure should be written on paper separate from the notebook. This information will provide the basis for your laboratory work. The actual work you carry out will be recorded in the notebook. Laboratory quizzes will contain questions to ensure prelab preparation. Quizzes: Approximately eight unannounced quizzes will be given during the semester. These short quizzes will cover the topic or topics assigned to be covered that day in class or earlier. Students are responsible for background reading on these topics. Spectroscopy concepts and problems will be included In the quizzes. Homework: Several homework assignments will be required. Final Examination: A final examination will be given during the last class meeting in the regular laboratory classroom. The exam will be comprehensive and is required of all students.

3 Laboratory Grading: Grading will be based on credit awarded for various activities distributed as shown below. Activity Points Lab Reports 170 points Participation 20 Safety 25 Prelabs 35 Lab Exam 50 Total 300 In grading lab reports s, I will be looking for the following: a. The Title of the experiment. b. The date on which the experiment is performed. c. Your name and your lab partner s name, if any. d. Abstract: The abstract should briefly describe the topic, the principal findings, and the conclusion. It should be written last to reflect the content of the report. e. The procedure that you followed. This may be in outline form i.e. a list of steps that you followed or if you are using a procedure from a book or journal, you may refer to that book or journal, you do not have to recopy the whole lab procedure. For example, you may write Followed procedure in Mohrig, -- page 35, with the following changes also, you need to give a flow chart. f. Your observations, which should include: color changes, formation of precipitate, temperature changes, etc. g. List of chemicals & masses (and possibly volumes) and physical properties (MP, BP, molar mass, density etc ) of reactants and products used. h. A balanced equation for all reactions (if any). i. Calculate the % yield (or recovery) of products. Show all work. j. The physical properties of products: Color, crystal size and shape, smell, etc. IR spectrum. k. Determine (by experiment) the melting, boiling point of your product and compare to the melting point or boiling point of the pure product. (This can be obtained from the CRC Handbook or Merck Index) l. Discussion: Explain any possible errors (like poor yield or 100+ % yield). m. Lab Reports are due one week after you complete the experiment. Late reports will lose 2 points per day. n. Each experiment will be graded on a scale of 10 points. PRODUCTS: The products i.e. the compounds you synthesize or recover will be collected and checked for amount and purity.

4 Chem 212 Dr. Chan Lecture: 5:10-6:35 Page 4 Spring 2016 chem212@gmail.com Lab: 6:40 9:55 II. Course Grade: Examination and Final Grade Distribution: Final exam in the lecture will be comprehensive. Final grades will be assigned primarily on the basis of points accumulated as follows: Activity % Points Final Grade Distribution Exams (3x100) pts A % Final Exam pts B 88-77% Quizzes pts C 75-65% Lab pts D 64-50% Home Work pts Total 750 pts A passing grade will be contingent on successful completion of assigned experiments. There will be no make-up lab or exam. A grade of zero will be assigned for a missed lab or exam. Attendance: You are expected to attend all lectures and labs. You are responsible for information, exam announcements, date changes, etc. presented in class, whether or not you are present. Students who are absent for 3 consecutive class meetings or 6 class meetings throughout the course without presenting a valid excuse could be dropped from the class. You should turn off your cell phones (if any) while you are in the lecture room or laboratory. During Exams students may leave the exam hall only after submitting their exam paper to the instructor. A student who has left the hall for any reason during the exam may not be allowed to come back and finish the exam or make any changes in his/her answers. A student who comes to the exam hall after the exam is started, may not be allowed to take the exam if at least one student has left the exam hall before he/she came into the hall. Withdrawal From Class: You are responsible for your credit and enrollment status. Any student withdrawing from class must officially inform the admissions office of his/her decision. Students who fail to follow the correct procedure for withdrawals will receive a grade of F for the course at the end of the semester. For important deadlines, please refer to the spring 2011 semester class schedule. The college academic honesty policy (please read catalog) will absolutely be upheld in this course. Neither cheating nor copying will be tolerated.

5 Course SLOs: -Demonstrate understanding of basic organic chemistry concepts -Understanding the differences or similarities of concepts -Know the IUPAC names and structural formulas of organic compounds -Rationalize reaction mechanisms - Compare differences in reaction mechanisms. - Explain relationships between molecular structure and properties of compounds. -Recognize the effect of reaction conditions on the mechanism of the reaction In tests and final exams, during discussions and lab reports: - Short oral questions are asked during lecture to check the students understanding of concept being discussed - Students are asked to choose, from many possible reactions, the best method of synthesizing a given compound - Students are asked to write the names/and structural formula ( including stereochemistry) of organic compounds -Students are asked to discuss a reaction mechanism that involves addition, substitution, elimination and rearrangement - Students are asked to explain the mechanism of a reaction based on the property (ex. optical activity) or structure( ex. Stereochemistry, rearrangement) of products formed -Students are given structural formula of compounds and asked to predict the physical and chemical property of the compound qualitatively. - Questions are asked to predict the major product of a reaction based on reaction conditions, size of the reacts, and nature of the reagents used ( effect of : solvent, structure, size and nature of substrate and nucleophile / base, temperature etc) - Students are asked to give reaction conditions that will favor one reaction mechanism over the other in a competing reaction ( SN1 Vs SN2, E1 Vs E2 or substitution Vs elimination reactions) - Students are asked to propose a multi-step synthesis of a given compound - Organize and apply chemical knowledge - Students are asked to show their collected data to the instructor before leaving the lab. -Observe and collect experimental data accurately. - Students are asked to set-up their own experiments - Students are required to use (operate) lab equipment -Identify basic laboratory equipment for analysis -Purify samples - Students are asked to purify their products using physical means (recrystallization, distillation, filtration etc) -Use appropriate lab equipment and chemicals - Students are required to use (operate) lab equipment for analysis - Determine purity of products - Students are required to determine the purity of their products and include it in their reports - Students are asked to identify unknowns -Analyze the data and come to conclusions, and - Students are required to write a lab report based on

6 Chem 212 Dr. Chan Lecture: 5:10-6:35 Page 6 Spring 2016 chem212@gmail.com Lab: 6:40 9:55 write a report. -Calculate and compare percent yields of reactions -Explain observations Program SLOs: Utilize an appropriate and effective scientific methodology to analyze chemical and physical processes in the work place and in everyday living. Explain and analyze the chemical world â as chemistry is the basic science with connections to many careers. Research and interpret scientific literature. their observations and discuss their results in the report and write their conclusions. - The reports are collected and graded for accuracy, organization, analysis, and synthesis of information - Students are required to calculate percent yield of their reactions and include it in their report Students are required to systematically and logically: -Characterize samples -Classify unknowns -Identify unknowns -Students are asked to apply learned information in solving multi-step synthesis problems -Projects that show the application of chemistry in industry and in day-to-day life are assigned - Group work/discussions are assigned -Students are asked to read current scientific journals and write report on the topic Students are asked to methodically and logically characterize, classify and identify unknown organic compound samples Institutional SLOs: -Critical thinking -Quantitative reasoning -Technical competence

7 Chem 212 Spring 2016 Lecture and Lab Schedule Lecture Text: Organic Chemistry, Solomon, 11 th ed Lab Text: Organic experiments, Mohrig WK Date Chpt LB 1 2/08 14 Aromatic Compounds M Check in and orientation Video 14 Aromatic Compds continued 1 W Extraction of piperine Handout 2 2/15 Presidents Day - Holiday M No Lab meeting 15 Reactions of aromatic compounds 2 W Oxidation of cyclohexanol/tlc E /22 15 Rxns of aromatic compds - continued M Oxidation/IR analysis - continued E Phenols and Aryl Halides - substitution rxns 3 W GC and IR and HNMR Analysis TBA 4 2/29 21 Aromatic Substitution - continued 4 M Nitration of Methyl Benzoate / TLC Handout 16 Aldehydes and Ketones I: Nu Addition 5 W Alkylation of 1,4- Dimethoxybenzene Neckers/E22 5 3/07 16 Nucleophilic Addition - continued M Photoreduction of Benzophenone Handout 17 Carboxylic Acids and their Derivatives 6 W Exam 1 ( Chapt 14, 15, 16, 21) 6 3/14 17 Carboxylic Acid derivatives 7 M Identification of alcohols [ QA ] Handout 17 Carboxylic Acids - continued W Identification of aldehydes and ketones Handout 7 3/21 18 alpha-carbonyl compounds M Aldol condensation/ir P alpha-carbonyl - continued 8 W Synthesis of isopentyl acetate E /21 19 Rxns of carbonyl compds M Synthesis isopentyl acetate-cont E Rxns of carbonyl compounds contd 9 W Grignard Synthesis -I Handout 9 3/28 19 Rxns of carbonyl compounds contd M Grignard Synthesis II Handout Review for Exam 2 W Exam 2 (chapts & 19 ) 4/04 Spring break Spring break 4/06 Spring break Spring break 10 4/11 20 Amines M TBA 20 Amines - Continued 11 W Phase transfer catalyst E /18 22 Cabohydrates- monosaccharides M Phase transfer catalyst - continued E Carbohydrates-disaccharides 12 W Isolation of lactose Handout 12 4/25 23 Lipids 13 M Glucose Pentaacetates P lipids-continued W Glucose Pentaacetates P /2 24 Amino acids and Proteins 14 M Syn. of Benzoyl Amino Acid / TLC E Amino acids and Proteins 15 W Synthesis of 5,5 -diphenylhydantoin Handout 14 5/09 25 Nucleic acids M Exam 3 ( Chapt 20, ) 25 Nucleic Acids - continued 16 W Synthesis of p-aminobenzoic Acid/TLC Handout 15 5/16 Review / Discussion M Checkout and Lab Final Review / Discussion 16 5/23 Review / Discussion 5/25 Review / Discussion 5/30 Memorial Day Holiday Holiday : Final Exam : Wednesday (6-2-16) 5:10 Pm

8 Chem 212 Dr. Chan Lecture: 5:10-6:35 Page 8 Spring 2016 chem212@gmail.com Lab: 6:40 9:55 Chem 212 Spring 2016 Text: Organic Chemistry; Solomons 10 th Edition Suggested Homework Problems. Chapter 14: Review Problems: 1 (a-d), 4, 5, 6, 7, 8, 13, End of Chapter Problems: 16 (a-p), 18 (a-l), 20 (a-b), 21, 23, 30 (a-c), 31, 32, 34, 35, 36, 37, 38, 39, 43 => Turn in problems: 18 a b c e f j; 30 all; 31; 34; 36; 39; 43. Chapter 15: Review Problems: 1, 2, 4, 5, 6, 7, 8, 9, 11, 13, 15, 16, 17, 18, End of chapter problems: 24b, 30 (a-e), 31 (a-c), 33 (a-e), 34 (a-c), 35 b d e f, 36 a b c, 38 a b, 43 =>Turn in problems: 24 a; 26; 30 a b d e; 31; 35 e g I m; 36 d; 43 Chapter21: Review Problems: 1, 2, 3, 4, 6, 7, 13all, 14all, 15 all, 16all, 17 a-d, 18 d f, 26 a b, 32and 41. Turn in problems:14 a b d, 15 a and b, 16 b and c, 17 a b c, 18 b c d, 26 and 41. Chapter 16: Review problems ( 4, 5, 6, 7, 9, 10, 11, 12, 13, 16, 17, 18,) End of Chapter problems: 20, 22, 23, 24 (a-d), 26 (a-d), 28, 30 (a-j), 33, 36, , Turn in problems: 20 (a b c e g j h; 22 c e; 23 a c f; 24 b c d; 25 b d; 27 c; 28; 30 a b f; 33; 36; 47 Chapter 17: Review problems: ( 1, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 14, 15, 16, End of Chapter Problems: 18 (a-f), 19 (a-d), 20, 21, 22, 23, 25,27 (a-c), 28 (a-f), 29 (a b d, e), 30 ( b c d e), 31 (d e), 33 a, 35(b d), 36, 41, 46 9a-e0, 48, 53. Turn in problems: 21, 22 b c e f 23 f, 25 f, 28 b e, 30 d, 31 d, 36 b, 41 all. Chapter 18: Review problems (1, 2, 3, 7, 8, 9, 10, 11, 12 a b, 13, 14), End of Chapter Problems: 15 a b c, 18 a b e f, 19 b, 20 a d, 21 a b d, 22 a b, 23a, 25 b, 26 a b 27 a d g, 29, 33 a b. = >Turn in Problems: 22 c, 25b, 28, 29. write complete equations in each case. Chapter 19: Review problems (1, 2, 3, 5 a b, 6a, 7, 9 a b c, 10 a b c d, 11, 14, 15 a b c, 17 a b c, 19a, 21a) End of Chapter Problems: 23 a b e, 24 a b, 25 b, 26, 31, 33 a-e, 34, 35 a b d f, 36 a c d, 38 a b, 41 a c, 44, 47 a b, 48 a d, 49, 60., Turn in Problems: 23 b e, 24 a, 33 c, 35 a, 36 e, 41a, 47 c, 49. Chapter 20: Review problems ( 1, 2, 3, 5, 6, 7, 10, 15, 16) 20 (a-e), End of Chapter Problems: 21, 22 a b, 23 c, 24 b c, 25 a d k, 26 b e, 27 a b e, 30 a b c, 31 a b, 32 a f, 40, 46, 49. => Turn in Problems: 26 a b d, 30 b, 31 n, 32 a, 40, 46. Chapter 22: Review problems ( 3, 6, 7, 9, 10, 11, 12) 20 all, 22, 27, 32, 33, 38. Chapter 23: 2, 3, 4, 5, 8, 12 (a-g), 13 (a-d), 19, 22 a. Chapter 24: 1, 2, 5, 6, 8, 9, 12, 13, 17 all, 18 all, 22, 23, Chapter 25: 10 a, 11 a b, 12, 13, -: END :--