CHEM 222 Santa Barbara City College Alcohol Oxidation 3 Lab Report
This week we will be doing both a Virtual Labz "worksheet", as well as a formal lab report based on a filmed experiment! This week's topic is on alcohol oxidation and reduction of a carbonyl compound. If we were in the lab, we would oxidize borneol to camphor and then take that SAME sample and reduce the camphor to isoborneol (stereoisomer of borneol). This is to introduce you to redox chemistry in a lab, and the idea of synthesizing something, purifying it, then using it to make something NEW; this process is a very simplified version of a multi-step synthesis. Since we have two experiments a week this semester, I don't want to assign you two formal lab reports, so instead of "performing" the oxidation of borneol to camphor, we will do an alcohol oxidation simulation. Details of the lab report are in the Experiment 2: Virtual Labz 12-3: Alcohol Oxidation-3 tab in this weeks module! In addition to the Virtual Labz worksheet, you will need to submit a formal report on the Reduction of Camphor to Isoborneol (Experimental Video). To improve your lab report write-ups, I have implemented a new type of assignment. You will be required to conduct a peer review of TWO CLASSMATES. Details will also be provided in the Experiment 3: Reduction of Camphor to Isoborneol tab in this weeks module. This week's Exp 2 is a Beyond Labz simulation where you perform the oxidation of an alcohol. You have to decide which alcohol to start with to obtain the desired compound 3-methyl-cyclohex-2-enone (details given in the procedure). You will also have to decide the appropriate oxidizing agent. Once you have completed the simulation, typically we fill out the worksheet and submit this as a pdf on Canvas, but this time we are trying something a little different. You can still fill out your worksheet for your records, but your submission on Canvas will be in the form of a multiple choice/dropdown box format using roughly the same questions. This is to expedite your receipt of the correct answers, since there are now TWO lab reports a week. Note: You will have to submit a proposed mechanism for this oxidation process. While it will differ SLIGHTLY from what we have learned in lecture, there are two logical mechanistic pathways one might propose. Once the alcohol oxygen has bound to the Cr, it may help to view this Cr complex as a leaving group as well as a nucleophile :) Yikes! I've said too much haha! Anyway, this should be fun! After completing Exp 2: Virtual labz : 12:3: Alcohol Oxidation-3, please complete this multiple choice "worksheet". In the past, the worksheet is a fill in the blank type of question assignment which you normally would upload as a pdf file with your responses to the questions. However, for this worksheet, we turned those questions into a multiple choice assignment. Please complete by Sun, 1/24 @ 11:59 pm. Choose the best answer. So this weeks formal lab report will be based on the reduction of camphor to isoborneol, an experiment that I have performed and recorded for your convenience. Sorry about some of the angles, I totally got a tripod, but forgot it at home :/ the video is still too legit to quit though. When writing your formal lab report, make sure to follow the guidelines laid out in the syllabusThis weeks formal lab report will be completed as usual, but is considered a rough draft. Once you submit your report (by Sunday 11:59PM), you will get assigned two PEER REVIEWS. You will complete these peer reviews by Wednesday, January 27, so your peer will have time to complete any improvements to their report and resubmit by Sunday, January 31. Keep in mind, next weeks experiment will still be due by that Sunday at 11:59PM, so the better you write your rough draft, the less work you have to put into your final draft. What you need to do...in bullet points :)Submit a QUALITY rough draft report by Sunday, January 24 at 11:59PM. (You will be graded on completion)Complete TWO peer reviews by Wednesday, January 27 at 11:59PM using the given rubric as a guide as well as providing written feedback to your peer. (More details to come, but you will be graded on quality of constructive criticism, but DON'T BE MEAN!!!)Submit final draft by Sunday, January 31 at 11:59PM.IMPORTANT NOTE: All peer reviews and reports will be anonymous on the students' end and only I can see who commented on each report so don't freak out, but also be kind and provide constructive feedback only. lab video https://youtu.be/bkKy_XDxTvELab report : the following is an outline of what your instructor expects to see in your lab reports. As long as the order and main titles (presented below in bold type) are present, the style is completely up to each student. A carbon copy laboratory notebook is required, and all work should be recorded directly in the notebook, not on scratch paper, as the work is performed. The written laboratory report includes the following areas:Name, Lab section or day/time and the complete title of the experiment should be written in the provided section on the top of each page.The Objective should indicate the purpose of the experiment in 1 to 2 sentences be clear and concise. If the experiment involves synthesizing a compound, meaning you make something new, please include a reaction scheme. A reagent table labeled as Physical and Chemical Properties of Reagents. Within this table should be the appropriate physical and chemical properties such as molar mass, melting point, boiling point, density, refractive index, amount needed, and at least one hazard and safety precaution for each substance. You can find this information in the CRC Handbook of Chemistry and Physics or online at a credible website, such as sigmaaldrich.com or https://sdbs.db.aist.go.jp and the proper reference should be indicated below the table. Calculations of theoretical yield and limiting reagent should be written below this table if the experiment is a synthesis.Equipment/Apparatus section will include a list of common glassware or equipment needed, such as spatula, Erlenmeyer flask etc. OR you may be required to draw and label the apparatus primarily used in the experiment of the day unless the apparatus had been used in a previous experiment, such as distillation. Since you will be observing the experiments in a video format I want you to write the Procedure according to your observations and my narration. This way, it will be in your own words and in a manner that you understand! Yay! It should, however, be written such that any organic chemist can perform the experiment when using these procedures. It may be a flow chart, paragraph, or bullet point as an example. The first time you perform a certain technique, for example, a distillation, you must describe how to set up and perform the distillation. If a subsequent experiment requires a distillation, you may simply state that the liquid was distilled.The above 5 sections are called the “pre-lab” and would typically be due upon entering the lab, but in this online format will be submitted with the below sections, called the “post-lab” and will include the following: Data and Results section is completed during the lab. Include all data obtained, observations (color changes, emulsions forming, liquid disappeared, melting point, crystallization), measurements (including tared masses), and results. Analytical results, such as an NMR spectra or IR should be attached at the end of the report. Calculations including items such as percent yield, or Rf values etc should be written out completelyThe Conclusions section should be used to interpret the data obtained. You should summarize your results of the experiment, including data such as yields, mp, bp, purity and how you came to this conclusion, % error, spectral analysis, literature values as well as any other necessary information needed to identify if the objectives of the experiment were achieved. You may also state whether or not the procedure was a good method for making the desired compound and any suggestions on improving the methods for future experiments. Possible sources of error, and how that error would affect the overall yield are extremely important to comment on.Here are the IR spectra obtained from the experiment: