CHEMISTRY 351 LABORATORY MANUAL WINTER 2021 FALL LABORATORY SESSIONS START JANUARY 25th, 2021 Winter 2021 Laboratory Coordinator: Dr. I.R. Hunt DEPARTMENT OF CHEMISTRY UNIVERSITY OF CALGARY Last revision: Jan 6, 2021 TABLE OF CONTENTS 1. Outline 2. Laboratory Coordinator 3. Academic Integrity 4. Attendance at the Laboratory 5. Missed Laboratory Sections 6. Grading 7. Preparing for the Laboratory 8. Laboratory Notebooks 9. Laboratory Reports 10. Safety and Waste Management a. Regulations b. WHMIS c. Safe Laboratory Practice d. Waste Disposal 11. Check In / Out Procedures and Department of Chemistry Breakage Policy 12. Useful References for Practical Organic Chemistry 13. CHEM 351 Homepage 14. TA Office Hours 15. Introduction to the Experiments Appendices: Equipment List Table of properties of common acids used in the laboratory Table of properties of common organic solvents Temporary Change of Laboratory Section Form Useful equipment volumes Spectroscopic tables H-NMR C-NMR IR Techniques (alphabetical) Pages Boiling point Determination (micro method) T 5 Chromatography (gas) T 13 Chromatography (thin layer) T 13 Decolourisation with charcoal T 2.3 Distillation (fractional) T 10 Distillation (simple) T 10 Drying organic solutions T 7 Extraction T 6 Filtration (simple) T 3.2 Filtration (hot) T 3.2 Filtration (vacuum) T 3.3 Fluted filter paper T 3.1 Greasing glass joints T 11 Heat sources T 1 Melting Point Determination (Mel-Temp) T 4.2 Melting Point Determination (Thiele tube) T 4.4 Recrystallisation T 2 Reflux apparatus T 12 Rotary Evaporation T 8 Sublimation T 9 Yield Calculations T 14 WHY ONLINE PDF ? The CHEM 351 student laboratory manual is available as a series of linked PDF documents. We certainly don't expect you to print all the pages, some can just be read online (e.g. the background information), but you will need copies of the pages that describe the experimental techniques and the individual experiment procedures during the laboratory sessions (no devices at the benchtop). There are several sections to the manual: • Introduction – that’s this document which outlines the laboratory part of Chem 351 including information on how to prepare for each experiment, keeping notes as well as grading and report writing issues. • Experiments - each experiment has at least two parts to it: o background information on the basis and context of the experiment. o experimental procedure - describes the work to be carried out. o report templates - are provided for some experiments where you “fill in the blanks” to complete your report. • Techniques – these provide stand-alone descriptions of how to perform the various experimental techniques that are integral to each of the experiments. In some cases, you will use a particular technique several times across the semester. NOTE : For safety reasons, no electronic devices (other than a simple calculator) are allowed on the laboratory benchtop work area. 1. OUTLINE. CHEM 351 is the first half course of an introduction to modern organic chemistry. Since organic chemistry is a practically based subject, the laboratory component forms an integral part of the course as it would normally introduce basic laboratory techniques while also investigating some of the modern concepts of structure, reactivity and reaction mechanisms of organic molecules in both simple systems and in the often more complex biological context. For W 2021, things need to be different because of the ONLINE nature of the activities. The focus will be on observation and interpretation, writing reports, and working through activities that directly connect to topics in other aspects of course content (especially some of the concepts of organic chemistry that students find difficult). Despite being online for Winter 2021, we have chosen not to totally rewrite this part of the manual or the experiment documents. We think you should be aware that laboratory work is REALLY supposed to happen in person, in a laboratory with you at the bench or fumehood. We know and understand that many of you don't want to be chemists, and you are required to take this course for your program or career aspirations because it was decided by someone else that the course is required, but everyone can benefit from some basic scientific training. For the online experiments, they are typically based on experiments we have used in the past that are known work when carried out correctly and with good technique. In general, they have been tried and tested over many, many years. Please remember that we all learn from our mistakes, and over time, our skills should improve. Please note that the style of this manual, it is written in a scientific style and NOT as a "point form". You are taking a University science course and the procedures are written as you would find them if you were to go to a scientific journal or a standard laboratory text book. A "point form" style generally discourages students from thinking for themselves, something that is both very dangerous in a real laboratory and very boring for the student. 2. LABORATORY COORDINATOR If you have questions or issues with the laboratory component of the course, then you should contact the Laboratory Coordinator. While the laboratory TAs can help with questions about the experimental work and the reports, it is the Laboratory Coordinator who is responsible for decisions about making up missed work, changing sections, exemptions, safety concerns etc. and it is your individual responsibility to communicate with the Laboratory Coordinator in a timely manner. Questions concerning the CHEM 351 laboratories in the Winter 2021 semester should be directed to the Laboratory Coordinator, Dr. Ian Hunt mailto:[email protected]. 3. ACADEMIC INTEGRITY We expect and require all students to conduct themselves in an appropriate academic manner in the laboratory and when completing laboratory related work such as writing reports, quizzes or tests. Therefore, we have a zero tolerance for "cheating" such as copying reports, quizzes or tests, or communicating with other students in quizzes and tests, or using "cheat sheets" or any other prohibited notes during quizzes or tests. We also have a zero tolerance for any attempts to interfere with the grading or the grades assigned as a part of the laboratory component. In the same manner as at an airport, where it says don't even joke about having a gun or a bomb, please don't even think about joking with your TA about changing your grade in exchange for you buying them a beer or a cooler, etc. We regard all such matters very seriously and they could result in an "F" in the course or worse. 4. ATTENDANCE AT THE LABORATORY In weeks where experiments are scheduled, students are required to attend their scheduled laboratory session that week via synchronous Zoom meeting. Like regular face-to-face laboratory sessions, students are expected to be punctual for the laboratory sessions and are expected to stay until they have completed the required work. If you can not attend your scheduled laboratory session (for the duration of your registered time slot, see section 5 below). Students who arrive late for a laboratory session will not be allowed to join the experiment and will be required to make up the laboratory in accordance with the information below. Like normal face-to- face laboratory sessions, the Zoom laboratory sessions will end promptly at the end of the period since in many cases, the next section starts in 30 minutes and TAs might have other laboratories or classes to attend. Zoom meetings will NOT be recored. 5. MISSED LABORATORY SESSIONS As per the Calendar and the Faculty of Science regulations (3.6 A “Missed Components of Term Work), students are required to notify the laboratory coordinator within 48 hrs of missing a laboratory section. Students are normally required to make up any excused absences e.g., those for which sufficient documentation has been provided to the Laboratory Coordinator. At the Laboratory Coordinator’s discretion, you will be allowed to make up other laboratory sessions that were missed for reasonable reasons. Absences can only be made up within a short time frame, and by prior arrangement with the Laboratory Coordinator. No absences can be made up once the same graded work has been returned to other students in the course. Each student is normally allowed only one laboratory make up opportunity per semester (except where prearranged special permission has been granted). If you don’t attend and perform the online experiment, then the grade for that experiment will be zero. In order to make up a missed laboratory section: 1. Complete the online "Temporary Change of Laboratory Section" form. PLEASE make sure that you read and follow ALL of the instructions on the form otherwise it will be returned to you unapproved for correction and resubmission. The information on the course website will allow you to find time slot with a laboratory section to attend. Once have completed the form, email a saved copy to the laboratory coordinator. 2. When the form is approved and returned to you, you will be provided with the information that you require in order to be able to attend the approved make-up laboratory section. 3. If a report was due in the missed laboratory period, then you should hand it in to the Chem 351 Laboratory Coordinator as soon as possible (certainly before the next laboratory session). Notes • If you try to make up an experiment without having the form first approved by the Chem 351 Laboratory Coordinator, then the TA will not allow you to join the online laboratory session. • Any report submitted without the complete Temporary Change of Section form attached for an experiment that you missed in your regular section will not be graded.