CHE 201 Organic Chemistry Microscale Lab Program fall 2015

Department of Chemistry CHE 201 Organic Chemistry Microscale Lab Program fall 2015 Lab director: Dr. Khalid Ahsan (ahsan@buffalo.edu); Office: NSC 301; Phone: 645-4115 Office hours: Monday and Thursday 1-2 PM and By Appointment REQUIRED TEXTS AND MATERIAL 1) Lab Manual: Multiscale Operational Organic Chemistry: A problem solving approach to the laboratory course, by John W. Lehman, 4 th custom edition for University at Buffalo, (2012). 2) Chemistry Notebook - Any bound chemistry Note book (or a composition book) can be used. Spiral bound notebooks or loose sheets in a 3 ring binder are not allowed. 3) Lab Materials: lab kit (same as CHE 101-2/107-8), monogoggle safety glasses, and a padlock for lab drawer are required (available at the bookstore). Proper protective clothing are required, long sleeve shirt, pants, and intact footwear covering the entire upper portion of the foot. You will not be able to work in the laboratory without proper clothing. Protective clothing is also detailed in the Laboratory Notes document available on UBLearns. Learning Outcomes and Objectives: Upon completion of CHE 201 laboratory course, a typical student should be able to: 1. Carry out experiment effectively and safely in the organic laboratory. 2. Perform micro scale reactions and synthesize organic compounds 3. Determine boiling point and melting point of product. 4. Perform purification of compounds by distillation, chromatography and recrystallization. 5. Identify products using boiling point, melting point and chemical analysis. 6. Take good experimental notes and data. 7. Write good laboratory report according to standard format of organic chemistry. 8. Develop good Team working and problem solving skills 9. Relate principles of chemical reactions and mechanisms to organic functional groups 10. Propose reaction mechanisms for common organic chemistry reactions IN THE LABORATORY Before starting any experiment A Laboratory Safety Quiz needs to be completed and students have to check-in and assume responsibility for all the assigned equipment.. A discussion of the theory, practice and methods will precede each experiment. These discussions will be held during the first hour of the lab period (recitation section). Please study the theory and familiarize yourself with the techniques required for all the experiments. Attendance of the pre-lab lecture and performance of each laboratory experiment is mandatory. A missed laboratory experiment cannot be made up at another time and any missed laboratory session will result in a grade of zero (0) for that experiment. Students who unavoidably miss a lab experiment must fill out and submit an excuse form (available on UB learns and Chemistry Copy Center NSC 361) within one week of their absence. STUDENTS WITH AN APPROVED ABSENCE* MAY BE EITHER ASSIGNED A MAKEUP ASSIGNMENT or PRORATED. You can only be excused from lab if you a Valid excuse that can be documented. 1

Please Note: Students who miss recitation WILL NOT be allowed to work on that lab and will receive a 0 for that lab. Lab Check-Out: All students must check out of their lab drawer during their regular lab period (with their lab instructor) during the week of check-out Nov 16-21, 2015). Those who do not are subject to a $100.00 improper check-out fee plus charges for broken, missing or unusable equipment as well as having the lock cut off the drawer. (Safety glasses and lab kits will be held in the stockroom for one month only). Students who drop the course during the semester must check out within one week of dropping to avoid the lab check-out charge. Students who are absent from check-out at the end of the semester because of illness must complete a waiver form, available at the Copy Center (NSC 361) to have this $100.00 charge waived. This form requires written documentation from a physician verifying the reason for the absence. Lab Safety and Regulations: Personal lab safety is very important when working in a chemical lab. Failure to abide by these guidelines may seriously endanger you and your fellow students, and WILL NOT BE TOLERATED. Deductions from your lab grade will be made for any behavior on your part which is inappropriate in a lab, or for failing to clean up your lab space before you leave the lab. More details are provided on page 3 of this document. Grading Policy: The laboratory component of this course comprises 25% of the final course grade [250 max points].to remove any grading inconsistency, lab grades will be normalized at the end of the term. This will mean that the averages in some sections will be raised or lowered. Any Problems regarding the grading policy should be directed toward the Course Instructors or Dr. Ahsan, not to the teaching assistants. More details are provided on page 5 of this document. CHE 201 Lab Exam: Lab Final exam (multiple choices, short answers and reaction equations) will cover material discussed in recitation, assigned readings, and procedures as actually done in lab. Students are also required to know basic principles of organic chemistry for the exam. Details will be provided later. ITEM ASSESSMENT SUMMARY(250 POINTS) EXPLANATION Data Sheet Tabulated raw data 2 points x 10 = 20 Lab Reports Final analysis of lab work 7 points x 10 = 70 Notebook- Personal record of lab work 2 points x 10 = 20 Lab efficiency Safety and technical proficiency 2 points x 10 = 20 Pre-Lab Quizzes-10 Assessment of Theoretical and Practical Knowledge (5 points x 10) = 50 Lab Final Exam Assessment of Theoretical and Practical Knowledge ( 1 x 70) = 70

Department of Chemistry LAB SAFETY AND REGULATIONS Personal lab safety is the most important consideration when working in a chemical lab. The following is a list of safety guidelines that need to be strictly followed. i. DO NOT PERFORM ANY EXPERIMENTS IN THE LABORATORY UNSUPERVISED ii. Wear splash-proof goggles at all times. State and Federal law require the use of safety eyewear by anyone working in a chemical laboratory. The Department has approved splash-proof goggles for this purpose. These are available for sale in the Bookstore. iii. Wear Chemical resistant Lab apron at all times. State and Federal law require the use of Lab apron by anyone working in a chemical laboratory. iv. Contact lenses are not recommended. Students need to sign a contact lens waiver form if they have to use contacts. v. Wear clothing (shirt, blouse, or dress) which covers and protects your chest, belly, sides, back, shoulders and UPPER ARMS. No cutouts or cutoffs, tank tops, tube tops, muscle shirts, etc. No peek-a-boo belly buttons either! The skin of your torso must not be exposed at any time in the lab. vi. Wear clothing (pants, long skirt or long dress) which covers and protects your body from the waist all the way down to and including your ankles. vii. SHIRTS MUST COVER YOUR CHEST AND ARMS COMPLETELY, SHORT SLEEVED, LOW CUT SHIRTS and BLOUSES ARE NOT ALLOWED. viii. SHORTS/SKIRTS ARE NOT ALLOWED. MID-LENGTH SKIRTS / SHORT PANTS (RIGHT BELOW THE KNEE) ARE NOT ALLOWED. ix. Do not wear clothing which is loose enough to knock over containers on the work bench or drag or dip into flames or chemicals. x. Wear shoes which cover and protect your feet completely. No sandals, flip-flops, open-toed shoes, or shoes with open sides or heels. SLIPPERS ARE NOT ALLOWED - THE TOP OF YOUR FOOT MUST BE COVERED! xi. Gloves must be worn when handling chemicals. Disposable gloves will be provided for each experiment. xii. Cleanup Lab Area: A clean area provided a safe working environment. Student need to clean up their lab bench and balance room area before they leave the lab. Failure to clean up will result in a deduction of points from your lab grade. xiii. No Eating and Drinking allowed in the lab. xiv. No Horse Play or other distraction allowed. xv. RUDE/ OBNOXIOUS/RECKLESS BEHAVIOR WILL NOT BE ALLOWED IN THE LAB AREA. STUDENT WILL BE EVICTED FROM LAB WITH THE HELP OF UB POLICE. xvi. USE OF LAPTOPS, IPODS, PDA S, CELL PHONES OR ANY OTHER DISTRACTIONS ARE NOTALLOWED DURING LAB. In addition to these you should also follow all instructions provided by your teaching assistant as well as other lab staff and instructors. Failure to abide by these rules may seriously endanger you and other students. VIOLATIONS WILL NOT BE TOLERATED. APPROVED MONO GOGGLES NOT APPROVED SAFETY GLASSES 3

Dates Aug 31-Sept 5 Lab #: EXPERIMENT No Recitation or lab Sept 7-12 Sept 14-19 Sept 21-26 Sept 28-Oct 3 Oct 5-10 Oct 12-17 Oct 19-24 Oct 26-31 Nov 02-07 Nov 9-14 Nov 16-21 Nov 23-28 Dec 1-7 No Recitation or lab Safety Quiz; LAB Check-In Lab 1: Introduction to Organic chemistry Worksheet. Lab 2: Learning Basic Operations [Lehman Exp. 1 page 2] Key techniques: Using a weighing balance; Separation, Density. Lab 3: Separating the Components of Panacetin [Lehman Exp. 2 page 10] Key concepts: Acid-Base reactions, Stoichiometry Separation, extractions. Lab 4:Identifying the Constituents of Panacetin [Lehman Exp. 3 page 18] Key techniques: Recrystallization and Melting point Lab 5: Properties of organic compounds -Handout on UB learns. Key concepts and techniques: Hydrogen bonding; Distillation & Boiling Point Lab 6: Synthesis of Salicylic acid (All parts except IR & NMR) [Lehman Exp. 4 page 23] Key techniques: Reflux, Recrystallization, Melting point Lab 7 Preparation of 2-chloro-2-methylbutane Lehman Page xvii Key concepts: Nucleophilic Substitution reactions.-chapter 4.7- Carey Lab 8: Separation of Unknown by Flash Column Chromatography-Lehman Page xxiv Lehman Key concepts: Polarity, capillary action, Separation Lab 9: Dehydration of 4-Methylcyclohexanol [Lehman Exp. 21 page 73] Key concepts: Elimination reactions Chapter 5.9- Carey Lab 10: A Diels-Alder Synthesis of 9,10-Dihydroanthracene-9,10α, β succinic acid Anhydride and LAB CHECKOUT No Recitation or lab-thanksgiving week CHE 202 Lab final will be held on Dec 2,3 and 4,2015 @ 6:00 PM. Students will be assigned the exact date and location for their exam in the week of Nov 2, 2015. APPROVED MONO GOGGLES NOT APPROVED SAFETY GLASSES

Department of Chemistry Lab Policies Objectives: To apply the knowledge obtained in Organic Chemistry lecture to problem solving in the laboratory. To develop good laboratory techniques; work safety; take data carefully; record relevant observation; use time effectively; assess the efficiency of your experimental method; plan for the isolation and purification of substances you prepare; and characterize substances you prepare by physical and spectroscopic means and synthesize organic substances. Please Note: CHE 201/202 (lecture class) is a co-requisite for this lab class. This means that if you drop the lecture class, you will automatically be dropped from the lab and should checkout of your lab drawer ASAP. Organic Labs at UB are considered controlled access areas, Students who have dropped lecture and continue to attend lab will be considered as unauthorized individuals and will be asked to leave the lab area. Preparation for Each Lab: The labs will require preparation and careful work to complete in the allotted time. Read all laboratory material before coming to lab. If pre-lab questions are assigned, complete the answers and turn in at the beginning of the lab. It is important that you understand the theory and procedure of the experiment. During the lab: Most labs are to be performed with a partner. In some labs you may be instructed to work alone. All data & observations should be recorded in your notebook. Use non-erasable ink, and never use white out. After completion of the experiment, fill the lab data-sheets (where appropriate) in a legible, tidy manner. After the lab: Clean up the lab space, clean the apparatus and put back to the drawer. Analyze the results and write a conclusion in your notebook. Academic Misconduct: Honesty in reporting results is one of the essential characteristics of your laboratory work. Little of your grade depends on getting "good" quantitative results. You will be more severely penalized for misrepresenting results than for honestly reporting "poor" results. You may discuss the lab results with other students, but you must complete all lab reports individually (even if you worked with a partner). Copying lab reports (any part) shall be considered academic misconduct, and as a result, may result in the grade of a 0 for that report and an additional penalty of 10 points. 5

GRADING POLICY The laboratory component of this course comprises 25% of the final course grade [250 max points] and will be determined as a percentage of the points received for each of the following items: Each experiment (Labs 1-10) will be worth 13 points. Frequent checks by the faculty will be made to ensure that grading is relatively consistent among individual teaching assistants. To remove any grading inconsistency lab grades will be normalized at the end of the semester. This will mean that the averages in some sections will be raised or lowered. Any Problems regarding the grading policy should be directed toward the Instructors or Dr. Ahsan, not to the teaching assistants. The emphasis on grading will be based not only on the number of points taken off for items missing but points given for work above the expected minimum requirement. 1) PRE-LAB QUIZ: 10 x 5 PTS = 50 POINTS Quiz graded by TA s from another section. Students efficiency to conduct each lab can be increased by ensuring that they are well-prepared for the lab through the administration of lab quizzes. Before coming to the laboratory, students must read the experiment and complete a pre-laboratory quiz (after recitation) for the lab that is to be done. The pre-lab quizzes will be given in your assigned lab before recitation and will be for 10 mint duration. The pre-lab questions will test students overall knowledge of the procedures, substances, theory, and calculations for each experiment. Students who miss recitation will not be allowed to perform the day s lab. 2) LAB FINAL EXAM 1 x 70 POINTS. Final will be graded by TA s from another section. Lab final will be held on Dec 2, 3 and 4 @ 6:00 PM students will be assigned the date and location of exam 2 weeks prior to the lab exam. The exam will cover material discussed in Recitations, Assigned readings, and Experimental Procedures as actually done in lab. Students are required to know Basic Organic chemistry principles for this exam. Practice Lab Final will be provided 2 weeks prior to the lab final. 3) LAB EXPERIMENTS (10 @13 PTS EACH) =130 POINTS. * Falsifying data and plagiarism of any sort (including copying from partner s lab report and internet websites) will not be tolerated and all parties will be penalized. Lab experiment points are further subdivided into the following: 4A) Data Sheet: (2 points): Blank data sheets will be available from UB learns. These are to be used for recording collected data and other values and calculations; % yield, grams, moles, color, phase (liquid or solid), melting point or boiling point of your product(s). Data sheets need to be submitted to your TA at the end of each Lab period. These will be used to compare the results and observations that you include in your lab reports. Lab reports without a corresponding data sheet will be awarded 0 point. 4B) Lab Report (7 Points each): To be written after you leave lab due within 1 week after conclusion of experiment. In a formal laboratory report, students describe the problem undertaken, the methods and materials used, the data collected, the conclusions drawn, and the arguments supporting the

Department of Chemistry conclusions. Laboratory reports should reflect high-level thinking skills and should not include completion items from a manual or answers to lists of questions. Lab report should be written in past tense, third person (e.g.: 3 grams were weighed, rather than Weigh 3 grams). If you don t understand how to do this, please ask your TA. Report should be either typed or Handwritten (single side only). Sloppy and untidy work will be penalized. i. Introduction: (a). Title and purpose of the experiment. (b) The reaction itself (include mechanism) ii. Procedure/Results: (a) State briefly state what you did in paragraph form. You may reference your lab manual for the specific procedure, indicating any changes. (b) Report the grams, moles, color, phase (liquid or solid), melting point or boiling point and the literature melting or boiling point (make sure you reference your source) and the IR of your product. (c) Calculate the % yield iii. Discussion: (a) Restate your yield. Discuss why your % yield was not 100%. You must do this by identifying sources of error that are inherent in the experiment. These include side reactions that could occur to form by-products, your mistakes made in the experiment, spills, etc. Suggest ways in which you would modify the procedure to improve your percent yield. (b) Restate your MP or BP range (e.g. 155-159 C). Discuss why your melting or boiling point was not the same as the literature value. Compare the two values here. (c)describe whether or not your methods of characterization (i.e. MP, BP, IR [CHE 202 only] supports identification and/or purity of your product. (d) If your product did not come close to the expected result, then describe why you think may have gone wrong. iv. Conclusion (a) Describe the purpose of the experiment and whether or not it was achieved as supported by the evidence. (b) Include at least one suggestion on how you would improve this lab. 4C) Lab Notebook*(2 points each): *Students should use the Organic Chemistry Notebook - Hayden-McNeil (available at UB book store) or a similar note book Notebook pages will be checked at the beginning of each lab and then signed by your TA at the end of each lab period. Notebooks will be randomly checked by the Lab director (Dr. Ahsan) A Lab notebook is both a chronological record of a student s laboratory work and a means by which the student can record analyses and interpretation of data, conclusions, and understandings gained. During the laboratory activity students can use Lab notebook entries to record revisions in procedure, modified hypotheses, or questions which occur to them. i. Introduction: The reaction itself (include mechanism if appropriate) ii. Table of Reagents: (a) List all reactants, solvents, and products (b) Densities, Mol Weights, Grams/mLs and moles to be used. iii. Procedure: This needs to be done as you are working on your actual lab experiment. It should include (a) What you actually did during the experiment include any last minute changes. (b) Your Observations & (c) Data and other values and calculations. iv. Summary of Data: % yield, grams, moles, color, phase (liquid or solid), melting point or boiling point (make sure you reference your source) of your product(s). 7

Students are not allowed to PASTE anything in their Lab notebooks-all information should be handwritten 4D) Laboratory Performance* (2 Points): The following Lab performance assessment guide has been adapted from a Rice University website [Ref:www.ruf.rice.edu/~bioslabs/assessment/performance] Expectations and performance criteria: You are expected to be punctual, prepared, to work efficiently and responsibly. Most of the specific criteria listed here will be used to evaluate you for the performance points i. Courtesy: Cleaning up your lab station and keeping common areas such as sinks, hoods, and balance area neat and tidy. Think before you drop a backpack in the middle of an aisle, or pour something into a clogged sink or a waste bottle that is full. ii. Attentiveness: During pre-lab listen carefully for, changes to a protocol, locations of supplies and equipment, tips to use equipment, etc. Conversing during recitation, working on an assignment, or sleeping is not recommended behavior. iii. Preparation: Know the objectives of the Lab and how to achieve it. Review the write up of the laboratory study and make an outline of procedures. iv. Responsibility & teamwork: Responsible students work safely and are carefully. They do not waste supplies, damage equipment, throw away product, forget to enter data, or enter data it incorrectly. v. Efficiency: Students who finish earlier than most while successfully completing their lab work are usually noted as being efficient. Students who take an exceptionally long time usually do so because of some omission in a procedure, unfamiliarity with the protocol, inattention to pre-lab etc. It is especially inefficient to "trade" notes when you and your partner have finished the lab work. Such practice suggests that you've missed the whole point of timely recordkeeping. You are both equally responsible for a complete laboratory record. If you simply copy your partner's notes you miss the opportunity to ensure that the notes are complete and accurate. Effective Communication with your partner during the lab allows you to catch each other's mistakes, and helps maintain good record keeping.