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Chem 213 Ochem Laboratory Experiments] Spring 2018 [CHEM 213 OCHEM LABORATORY EXPERIMENTS] Experiments & Exam Schedule ~Spring 2018~ Date What’s due? Week Exp.# Topic 2018 Prelab (PL), Report (R) Safety Contract, Check-in Introduction, Safety, Check-in 1 1-16 16 Sheet, PL 16 How to write-up a Lab Experiment using EXP 16 2 1-23 17 PL: 17 Nitration of Methyl Benzoate 3 1-30 18 PL: 18, R: 17 Friedel-Crafts Acylation 4 2-6 R: 18 Exam 1 Exam 1 review 5 2-13 19 PL: 19 Reactions of Alcohols & Phenols 6 2-21* 20 * Due Wed: PL: 20, R: 19 Synthesis of Alkenes 7 2-27 21 PL: 21, R: 20 Reduction of Ketone to form a Diol R: 21 8 3-6 EXAM 2 Exam 2 review Spring Break 3-12 to 3-17 9 3-20 22 PL: 22 Aldol Condensation 10 3-27 23 PL: 23, R:22 Reactions of Aldehydes & Ketones Lecture 11 4-3 R: 23 EXAM 3 12 4-10 Nothing Campus Closed Tuesday April 10 13 4-17 24 PL: 24 Isolation of Milk Protein 14 4-24 25 R: 24, PL 25, R:25 Soap Synthesis & Check-out 15 5-1 Nothing EXAM 4 16 5- 7 & 8 Monday May 7: Poster due Tuesday May 8: Application Project Poster Session 17 Return Loaned Books: You must turn in loaned 18 5-21? books before final exam to get a final exam. Final Exam (TBD) ___________________ @ 7:30 am All papers, exam reviews, experiment prelabs (PL) and lab reports (R), are due before 7:20 am. NO LATE REPORTS OR PAPERS ACCEPTED. Technological problems (printer, computer, ink, etc.) are not acceptable excuses for late reports or papers, so start early. Labs: For each experiment you are responsible to prepare and read over lab text and lab notes to understand the general principles. You are required to turn in a purpose and procedure for the experiment before lab starts. The purpose and procedure is written in your lab notebook and the carbon copy given to me. If you do not turn in the purpose/procedure on time, you will not be able to perform that experiment (No makeup labs allowed). I will start every lab with a short discussion of safety and lab technique. If you arrive late, I cannot allow you to perform the experiment. I will not tell you how to do the experiment step by step. You are responsible to have read the material with an understanding of the experiment and what you need to do before you come to lab. If I feel you are unprepared for the lab, you will be asked to leave without credit for the experiment and no makeup lab allowed. APPLICATION PROJECT (60 PTS) You will complete research and present a poster to the class. Key Due Dates and Times Topic Approved by Instructor: Monday March 26th (each day late -5 points) You must post your organic compound on the Discussion Board in Blackboard; each student must have a different compound) Poster turned into lab room: Before Monday May 7th @ 7:20 am (Early posters encouraged, do not be late to lecture) th Poster Session: (Attendance mandatory) Tuesday May 8 @ 7:30 am Copyright © 2018 K. Boebinger 1 Spring 2018 [CHEM 213 OCHEM LABORATORY EXPERIMENTS] Only use analytical balances for this course for ALL mass measurements. Issued Laboratory Equipment: The student is responsible for all issued equipment as well as the key. Points may be deducted for missing or broken equipment and/or key. Point values will be determined by the instructor. The student is responsible for taking an inventory of the drawer and hood equipment during both the check-in and check-out process or when dropping the course. The student is responsible for the cleaning of all equipment after each experiment and also at the time of check-out. Any student failing to check-out of issued lab drawer and taking inventory of equipment may result in a hold being placed on transcripts and registration. Dress Code for Lab: Eye protection must be worn at all times anyone is performing an experiment in lab, even if you are finished. Goggles or safety glasses may be purchased from the bookstore or hardware store. Goggles will fit over prescription glasses. If you wear shorts or skirts to class, it must be knee length, or you must wear an apron or lab coat. You must provide your own, the bookstore will have some available for purchase. No opened toe shoes, exposed tops of feet, nor sandals may be worn in the lab. Refusal to comply with the above rules will result in your earning a zero grade for the experiment for that day, and you will not be allowed to do a make-up for missed work. Laboratory Report: Each experiment completed correctly and handed in on time will be graded on a 20-point basis. All experiment reports due approximately 1 week after lab is scheduled, before the lab or exam starts (see page 1 for due dates). Late reports will not be accepted for any reason. If you know you cannot attend, then you may have a student turn in the report on time for you. All experiments include spectroscopy this term. What is due before or at the end of lab for the Lab Report: a) Purpose: Written in your lab notebook along with the procedure, and the copy turned in before the lab starts Read the experiment to determine what the purpose of the experiment is. The purpose is the reason for doing the experiment, and it is a couple of sentences, or a short paragraph. The purpose should also include the name(s) of the reactants and/or products and must include any reactions, or equations for the experiment. If MP or % yield will be determined, include a statement such as “purity of product will be determined using melting point range’, and/or “percent yield of product will be calculated”. (2 pts) b) Procedure: Also written in your lab notebook along with the purpose, and the copy turned into me before the lab starts. The procedure must be in enough detail, so that the experiment can be performed from just your notes. This must include materials list and equipment needed, and a brief sketch of the lab apparatus or set up with each piece clearly labelled. This is turned in before the experiment is performed. (3pts) c) Data: This is written in your lab notebook. It should be prepared before you come to lab so that during the experiment, all you need to do is fill in the data and turn in the copy to me as you leave, at the end of lab. Be sure to write this on a separate page in your notebook from your purpose and procedure, since this is turned in at a different time. I do not return these to you. (1 pt) What is due the following week for the Lab Report: Report: The front and first page is the Report page from this packet where you write your name, (for Exp 16 that is page 4). Complete all sections and questions on the report page, including the spectroscopy sections in the space provided. Do not write answers to questions in the lab notebook. Then attach the page(s) written in your lab notebook, clearly label each section: Calculations, Graphs, Conclusion*, and Sources of Error. *The conclusion must include results such as MP, unknown number and identity, % yield, etc. Questions on the report pages need to be answered directly on that page, and not written in lab notebook. (14 pts) You are responsible for understanding the information in your Zubrick lab text. The lab text is your guide to organic lab techniques required for this course. For example, if the directions ask you to recrystallize, look up recrystallization techniques in your lab text. Standard laboratory techniques, safety, and brief theoretical discussions are described in the text. It is your responsibility to read and understand the information before you come into lab to perform the experiments. If I feel you are not properly prepared for the experiment, you will be asked to leave the lab, no credit will be given for the experiment, and no make-up lab is allowed. Copyright © 2018 K. Boebinger 2 Spring 2018 [CHEM 213 OCHEM LABORATORY EXPERIMENTS] Experiment 16: Synthesis of trans-Cinnamic Acid Carboxylic acids are the most common class of organic acids that are encountered. The pKa values of carboxylic acids range 3-5, classifying them as weak acids. Phenols are only slightly less acidic, while alcohols, ketones and terminal alkynes are much less acidic. This experiment will synthesize a carboxylic acid from an iodoform reaction of a methyl ketone; the reaction will result in a loss of a carbon from the chain. The oxidizing agent is commercial bleach which contains 5% hypochlorite. This synthesis will take place in two steps; Reaction 1st A haloform reaction using hypochlorite (NaOCl) as the oxidizing agent NaOCl + HOH + NaCl 2 NaOH + Cl2 2nd Oxidation of the methyl ketone to a carboxylic acid. + O O H O + NaOCl (Cl2, NaOH) CHCl + C C C 3 - + R CH3 R O Na R OH H O H O 1. NaOCl, H2O C C C C + CHCl3 C CH3 + C OH 2. H H H trans -4-phenyl-3-buten-2-one trans-cinnamic acid MM = 146.19 g/mol MM 148.2 g/mol Procedure: 1. Place 0.300 g trans-4-phenyl-3-buten-2-one (benzalacetone) and one boiling stone in a 10-mL round bottom flask (You will Not be using the conical vial or spin vane as shown in the picture, be sure to draw the round bottom flask in your sketch for the prelab).
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