The CHEM 233 final exam is scheduled for Monday, December 7 in room 250 SES from 6:00-8:00 p.m. For more information, download the file "finalinfo_F09.pdf" from the orgo labs file sharing page. This document contains information on exam conflicts, policies, format and sample questions. It also has reminders for the lab notebook due date and the practical exam.

Tags: final exam

The experimental procedure for Lab 9 (diazo coupling) has been revised. The diazo coupling reaction will now be performed at reflux, which precludes the need for purging the reaction flask with nitrogen. You may download the revised procedure from the Shared Files page. This procedure replaces the one found in the course manual. Use the new procedure when writing your pre-lab entry. Sorry for the late notice.

This semester UIC has asked all instructors of 100- and 200-level courses to enter midterm grades. I have entered midterm grades for CHEM 233 so that you can make informed decisions about your work in this course. The midterm grade was determined from your scores on lab reports 1-6 and the midterm exam. You will be able to view your midterm grades using the Student Self Service Login at 5:10 p.m. Friday, Oct. 23. Your TAs have also been given your your midterm grades and can provide you with your current percentage score in the course, which will give you a clearer picture of your standing. I have also posted the course curve and midterm curve on the Grades Fall 2009 page. For more information on midterm grades, visit the Office of Admissions and Records site. If you'd like to discuss your standing in this course, particularly what quality of work is required to achieve your goals, stop by during office hours (M,W,F; 12-2 p.m.).

Tags: midterm grades

This semester I am instituting a new policy for making corrections to exams that have grading errors. If you suspect that an error has been made in grading your exam, first speak with your TA or myself to determine if in fact there is a grading error. If you are confident an error has been made, a formal letter must be written to me that clearly states the nature of the suspected error and the proposed adjustment in point value that will result from this correction. The letter and the original exam must be personally submitted to me in my office no later than 2 weeks from the date the exam was taken; these items may not be submitted to your TA. Original exams that are submitted for review will not be returned; be sure to make a photocopy for your records. For submission instructions and requirements, download the file "exam_corrections.pdf" from the Organic Chemistry Labs File Sharing Page.

Tags: midterm, corrections

The grading statistics for CHEM 233 are now posted on the Grades Fall 2009 page. I was hesitant to post these so early in the semester, but I did anyway since there have been several questions regarding lab report scores. Please do not over analyze these stats; currently, they only reflect the scores of the first two lab reports. They are meant to give you an approximate idea of how your scores compare to the rest of the class and how your TA's section average compares with the others. Remember, initially all sections are normalized to a 70% average (for lab reports only), which means that if your TA's lab report average is below 70% every student's lab report average will be raised until the section average is 70%. Likewise, if your TA's average is above 70%, every student's lab report average will be lowered until the section average is 70%. The stats will, of course, become more informational as more scores are added and when the scores of those students who have withdrawn have been removed. If you would like an individual detailed report of your grades, which will include your normalized lab report score, please stop by my office during office hours and I'd be happy to print one out for you.

This semester I am making a slight change to the steam distillation experiment (Lab 5). In addition to isolating (S)-(+)-carvone from caraway seeds, you are also going to isolate (R)-(-)-carvone from spearmint leaves. For more details on this modification download the file "steamdist_modification.pdf" on the File Sharing page. You will work in groups of two. One member of the group will isolate (S)-(+)-carvone from caraway seeds, the other will isolate (R)-(-)-carvone from ground up spearmint leaves. The spearmint leaves I purchased are dried. Since I'm not sure how much carvone is present per gram of dried leaves, we may need to increase the starting mass of spearmint leaves. We'll see how the first lab section goes and then modify as necessary. Good luck. It should be a very fragrant lab.

Two copies of the CHEM 233 textbook have been placed on reserve in the Science Library (3500 SES; 312-996-5396). You may checkout the textbook for use in the library for a limited number of hours. Be sure to bring your UIC student ID.

Tags: textbook

For those of you interested in a more graphical presentation of infrared spectroscopy, I made one of my previous CHEM 232 lectures available on that topic. You may download Lecture 9 on the the CHEM 232 page. The IR material begins in the middle of that lecture. Remember, one of the keys to utilizing IR spectroscopy requires that you know your basic functional groups and the bond types that make up that group. At the minimum you should be able to draw an example of all of the functional groups that were presented in the IR Primer activity on the first day of lab.

There is also a nice presentation of IR on the Michigan State University website and the CU Boulder website. Both contain several examples and a straightforward discussion of IR theory. The CU Boulder page is a little more exhaustive; it describes numerous IR bands that can be identified for several functional groups.

Tags: Infrared Spectroscopy

Since there have been so many questions, I wanted to elaborate on what lab notebooks are acceptable for CHEM 233. The only requirement is that the notebook must be spiral-bound. No loose-leaf sheets will be counted toward the notebook grade at the end of the semester. It does not have to be an "authentic" notebook like those solid in the bookstore. Having said that, I do recommend that you purchase a lab notebook with carbon copies that you can tear out. If your notebook is lost or stolen, you will at least be able to present the carbon copies as proof that you completed the notebook. If you do not choose to go this route, then at least make a photocopy of your entries each week as a backup. While we're on the topic of notebooks, remember that it will be graded at the end of the semester according to the notebook grading rubric in the course manual. Look at this rubric now, so that you are completing your weekly entries correctly.

Tags: notebook

The CHEM 233 course manual is now available at the UIC Bookstore (Student Center East).

Tags: manual, bookstore

CHEM 233 Course Manual Arriving at the UIC Bookstore Soon!

There are two required texts for CHEM 233:

1. Gilbert, J.C.; Martin, S.F. Experimental Organic Chemistry: A Miniscale and Macroscale Approach, 4th ed.; Brooks/Cole: Pacific Grove, CA, 2006. ISBN: 0-495-01334-X.

2. Landrie, C. Organic Chemistry Laboratory I: Lab Manual & Course Materials, Kendall-Hunt: 2009. ISBN: 978-0-7575-6240-2.

The second text above is currently being shipped and should be stocked in the bookstore by Tuesday, August 25, 2009. In the event that the lab manual is not available until the following week, the syllabus, front material and Lab One have been photocopied for you and will be distributed on the first day of class. You may also download that packet here. You will be responsible, however, for purchasing the lab manual before you complete Lab Two. Check back here for further updates on availability.

Tags: manual, bookstore

The summer 2009 CHEM 233 final exam will be on Thursday, August 6 from 6:00-8:00 p.m. in room 250 SES. Please download the final exam handout for more information on exam conflict resolution, makeup exams, policies, format, practice questions, exam topics as well as important reminders for the practical exam.

Tags: final exam

Long before I began teaching the undergrad orgo labs full-time, I was a TA for this course when I was a chemistry graduate student at UIC. At the time, there were few analytical techniques available for the characterization of organic molecules: no melting point apparatuses, no IR, no TLC and a sporadically functional GC with an unbearably slow analog plotter. A typical synthesis lab was often concluded by the students proudly shoving a yellow powder at me exclaiming, “See, I did it.” Sadly, I would acknowledge their accomplishment with a solemn nod, after which they would chuck their powder into the waste container with a strange jubilation. What was the point, I wondered. That yellow powder could have been anything. After about three years as a teaching assistant for this course, I was shocked one day when I found an infrared spectrometer in what is now the instrument room. I couldn’t believe we weren’t using this equipment in our labs. When I was hired as the full-time instructor, I made utilizing the IR my first priority. Of course, I quickly realized why this technique had been left by the wayside for such a large class: time. Time training TA’s and students, time creating instructional handouts, and time maintaining the spectrometer were all factors, but the time that it took students to acquire a decent spectrum was the most formidable challenge of all—primarily because of the difficulty students had with sample preparation. For liquid samples, students sandwiched a thin film between two NaCl plates. After the tenth plate was ruined by accidentally washing with and thereby dissolving in water, we switched to disposable PTFE cards. These worked well enough, but it was difficult to get spectra of volatile samples.

Solid samples had to be ground with anhydrous KBr and pressed with a die into a transparent disc. While seemingly straightforward, a number of conditions had to be met precisely right in order to obtain a disc of sufficient transparency and with a high enough sample concentration to acquire a spectrum in less than 5 minutes. The tension was palpable during these labs, especially when time was running short and the line for the IR wound outside the instrument room like a snake threatening to choke the sanity out of student and TA alike.

I’m happy to say, those days are over. The attenuated total reflectance (ATR) accessory, which I have fought to acquire since I began teaching this course, has arrived thanks to the differential tuition money that was made available to the Chemistry Department this year. After several tedious hours of tuning, aligning and swearing, the Pike Technologies GLADiATR was successfully installed. Then came the time of reckoning. After acquiring 64 background scans, I nervously applied a small amount of solid acetanilide to the 2 mm2 diamond crystal, lowered the pressure clamp and then turned the clamp dial clockwise until the pressure tip had pressed the solid into the diamond at 40 pounds of force. I clicked the scan icon on the screen and one minute later I was looking at my first successful ATR spectrum. The results were amazing. The total acquisition time from start to print was 3 minutes—a far cry from the 20 minute average for the KBr technique. Could it really be this easy? After twenty or so spectra later, the answer was a resounding yes. I was ecstatic. It’s a great feeling to know that this technology will radically change how IR is approached in CHEM 233 and I am anxiously awaiting to see how it will be received by the CHEM 233 students this semester.

Please click here for a full-color version of the instructions for using the GLADiATR accessory.

Tags: IR, ATR

A couple years ago I sat in on a lecture at UIC where the instructor was using technology that allowed her to poll her students during class. She would ask a multiple-choice question, which was duplicated on the overhead projector, and then her students would punch in A, B, C, D or E on their hand held clickers before the timer expired. Within seconds, the results of the poll flashed on the screen—eerily reminiscent of a Who Wants to be a Millionaire lifeline. I was hooked instantly. Not only do I love gadgets, Millionaire and statistics of every kind, but it also seemed like an ideal method for communicating with students in large lectures. Any teacher worth their salt continually asks themselves, “are they getting it?” Some are even brave enough to ask out loud even though they know the question will likely be regarded as rhetorical and disappear into the echoes of the lecture hall. What better way to find out then a reliable polling system such as iClicker?

You are wondering, of course, how this topic is relevant to the laboratory courses blog. In truth, it isn’t; however, next Spring I will be teaching one lecture of CHEM 232 (Organic I) and I am considering using this system. I’ve considered many of the advantages and disadvantages from my perspective. What I don’t know, however, is what students at UIC think are the primary strengths and weaknesses of this system. I would welcome any comments you have. Some key questions that must be considered are:

• What are good and bad polling questions?
• Should the system be mandatory?
• Should the questions be worth points? If yes, what percentage of the course?
• How many questions are too many in one lecture, one semester?
• Is the technology reliable? Is record keeping feasible?
• Will students remember to bring their clickers?
• How much do the clickers cost? Is this a financial burden?

Tags: iClicker

Phew! Grades for CHEM 233 are done. You can find summary statistics on the Spring 2008 grades page. Because of the large number of students in the course, I cannot respond to emails for grade requests. However, I will hold office hours this Thursday and Friday (5/8 & 5/9) from 11am to 4pm specifically to meet with students to discuss grades. No appointment is necessary. You may also contact your teaching assistant. Based on the summary statistics, this was a very successful semester with an above average number of A's and B's. For most of you, your hard work has paid off. Congratulations on a job well done. Have a great summer.

Tags: grades

The Spring 2008 CHEM 233 final exam is scheduled for Monday, May 5 from 6:00pm to 8:00pm. Please see the final exam information handout for information on the schedule, exam conflicts, policies, format and sample questions. There is a link to this file on the homepage as well as the shared files page. I will distribute a hard copy of the handout next week before your practical exam. Also, I just posted three sample exams for exam two.

Tags: 233, final exam, exam 2, sample exam

Wow, another whirlwind semester is almost done; it always seems to go by so fast. However, as I look at the upcoming schedule and the amount of work we have left, it seems like a long way yet to go. Perseverance, hard work and lots of coffee will get us their though. Remember that the week after your last lab is the practical lab exam (synthesis of luminol). I will provide you with an introduction and more details the week of your last lab (4/14-4/18) at the beginning of your sections; don't be late. Your laboratory notebooks are also due ON the day of the practical. Exam 2 is the following week (4/28-5/2); you will also check-out your lab drawers on that day. I will again post sample exams online within the next two weeks. Finally, I will distribute a flyer with information pertaining to the final exam two weeks prior. The flyer will include policies, conflict procedures, sample questions, etc. Have a great weekend...

Tags: practical, exam 2, final exam

FYI: I posted the exam 1 key for CHEM 233 on the bulletin board outside of my office as well as the curve & distribution graphs. As I posted the key, I noticed the bulletin board also needs to be spiced up with some new pictures. Pictures of you and your friends--in lab!! I have been meaning to take some new pics, but just can't seem to get around to it. So I decided that I'll leave you in charge of the pics. I'll give one extra credit point (max 5 points) to every CHEM 233 student who submits a picture which is approved to go up on the board. I will generally look for original, candid and lab oriented pics to post. Write your name and TA on the back and hand it to me or slide it under my door. If you see your pic on the board, you got the credit. Be safety conscious and be sure to ask permission before snapping a pic of your colleagues. Deadline: April 18.

Tags: exam 1, key, pictures

Congratulations on a job well done. I was very pleased with the results of exam one; it was apparent the majority of you worked hard on this material. The sample exams also seemed to contribute to more focused studying. I was particularly impressed with the number of students who seemed to have mastered functional group recognition in IR spectroscopy. The approximate curve (grade cutoff's) and score distribution have been posted on the Spring 2008 Grades page under the CHEM 233 tab. Remember that this curve is only approximate; the full value of each of your scores will contribute to the final score, which is then curved. If you would like to discuss your score or believe there is a grading error, stop by during office hours and I'll be happy to look over it with you. Note: your TA's will not be able to make corrections to your exam since the score has already been entered into my gradebook. Again, great job.

Tags: 233, exam 1, curve

I recently posted sample exams for CHEM 233. While I think studying from samples can be dangerous since this sometimes encourages students to memorize material rather than learn it, the samples communicate clearly the type, formate and difficulty level of content to be tested. My aim was also to eliminate any disparity between students without samples and those who acquired old exams from classmates who had previously taken 233. My recommendation is to use the sample exams as an evaluation tool after you have studied the material. Review homework questions, assigned reading, course manual readings and prelab lecture notes first, then attempt one of the samples to gauge how well you understand the laboratory concepts and techniques.

Tags: exam, exam 1, studying

For those students interested in subscribing to this blog as an RSS feed, click on the link entitled "Blog RSS Feed" at the bottom of the sidebar to the left of this page. There is another link above entitled, "RSS." This will simply open the RSS feed for comments only. To be honest, I'm not sure why that's there or how to remove it.

Tags: 233, 333

As many of you have already realized, there is a mistake in the textbook excercise # 5. You should use equation 8.4 (Hooke's Law), not equation 8.5. This question is very similar to 3 & 4. Also, while I'm on the topic of Hooke's law, let me point out that the masses in the equation refer to the mass of a single atom. The most common error is to use molecular weights, rather than atomic masses. You can find atomic mass by dividing the molar mass by Avogadro's number.

Tags: Hooke's, 233, Homework

Andy Freeman has asked that I let all students know that Friday, February 1 will be the last day that the stockroom will lone out goggles. Reminder: Students without goggles will not be allowed to participate in any laboratory activity.

Tags: goggles, safety, 233, 333

Wow! It's hard to believe we're almost through week 3 already. CHEM 233 students: Be aware that there were a couple mistakes on the prelab lecture transparencies for Lab One. These errors have been corrected in the pdf version, which you can download here.

As most of you have found out, lab one is technically challenging. Your successful completion of the lab on time depends to a large degree on your advance preparation. I strongly encourage you to carefully read the textbook material assigned in the lab manual--especially those sections dealing with new techniques such as boiling point, melting point and IR--before coming to lab. Your familiarity with these topics can potentially reduce your in-lab time significantly.

Tags: 233, notes, Lab1, IR

There was an error on the informational sheet distributed before the practical exam. The correct room for the final exam are as follows:

Monday - Thursday sections: Lecture Center A1 (6:00pm-7:00pm)

Friday sections: Lecture Center B1 (6:15pm-7:15pm)

Sorry for the confusion. You can find and updated final exam info sheet on the shared files page.

Tags: final

I posted a sample exam for exam #2 on the shared files page (233sample_ex2.pdf). You may work through this example to help you study. I do not recommend relying soley on this example; also look at homework questions and TA notes for additional material.

Tags: exam, exam 2, chem 233

There have been several questions about the stereoselectivity of an E1 elimination mechanism. Two arguments can be made. A kinetic argument compares the relative energies of the carbocation intermediates leading to each product. The carbocation intermediate on the left is more stable than the carbocation intermediate on the right due to reduced steric strain; therefore the trans alkene is favored. Because this reaction is reversible a thermodynamic argument can also be made and is actually more correct; although the outcome is the same in this instance. Thus, the trans alkene product is favored because it is more stable (lower in energy) than the cis alkene. Trans is more stable than cis for the same reason already mentioned, less steric strain. Caution: thermodynamic arguments (comparing relative stabilities of products) can only be made when reactions are reversible (equilibrium). This reaction is reversible and explains why distillation was necessary to remove the alkene products and shift the equilibrium toward products (LeChatleir principle).

Tags: chem 233, E1, elimination, stereoselectivity, distillation, kinetic, thermodynamic, LeChatleir, alkene, dehydration, carbocation

CHEM 233 final exam will meet according to the schedule below. The exams will start on time so please arrive early so that you may find your seat. Again, a final exam information sheet will be distributed on the day of your practical. Happy Thanksgiving.

Monday-Thursday sections: Monday, Dec. 10, 6pm-7pm, Lecture Center B1.

Friday sections: Monday, Dec. 10, 6:15pm-7:15pm, Lecture Center A1.

Tags: final exam, chem 233

Week 14 (November 26-30): Practical Exam

Week 15 (December 3-7): Exam 2 and Drawer Checkout.

Week 16 (December 10): Final Exam, 6pm, LC A1 & B1. Please see final exam info sheet to determine which room your exam is in.

Tags: final, final exam, practical, exam 2, chem 233

The final exam for CHEM 233 will be held on Monday, December 10 from 6-8pm in Lecture Centers A1 and B1. Because there are two rooms, the class will be divided in half. You will receive an informational sheet on the day of your practical exam that will indicate which Lecture Center you should attend. This info sheet will also contain sample questions, review topics as well as exam policies.

Tags: exam, final, final exam, chem 233

Well, I've finally entered the world of blogging after having spent probably hundreds of hours reading the blogs of others. It feels good, although I'm a little skeptical since I tend to be a perfectionist and reread my writing over and over until I am satisfied. I'm somewhat comforted that this blog is dedicated to organic chemistry--a topic I could write endlessly about. Initially, I anticipate the blog to more or less function as an announcement board for CHEM 233 and CHEM 333, especially for the remaining Fall 2007 semester. However, I certainly hope it can grow into a platform for initiating interesting discussions in chemistry. It may even be entertaining, but that might be stretching. . .