Links to download Zoom Lab Videos and PDF files
- Lecture Date: Tuesday, January 26, 2021
Welcome to the fist day of Chem 12BL. In this first class we go over introductions to the course. We take a look at the website used for the course at https://ChemEd.study in addition to the Canvas shell. We discussed the layout of the class, what the lab is likely to be like and the grading scale. We also introduced the Grignard reaction, it's historical relation to the Barbier reaction, and how the reaction in general works.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, January 28, 2021
In todays lab session we cover experiment 33A The formation of triphenylmethanol by Grignard reaction. This reaction covers two to three days worth of lab exercises. The first day involves the reaction of bromobenzene with magnesium metal to afford the Grignard reagent phenyl magnesium bromide and it's subsequent reaction in situ with benzophenone to afford the insoluble triphenylmethoxide ion adduct. The second and third days involve the acid work-up of the adduct to afford triphenylmethanol, the isolation and characterization of the product including melting point, FT-IR spectroscopy and percent yield determination.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, February 2, 2021
The Grignard wet lab is being broken into four videos that span setting up the apparatus, conducting the reaction, isolating the product, and characterization of the product. The first three of the videos are below. This lab traditionally takes most students three full lab periods, or 9 hours of work to complete. The characterization video will be filmed this Wednesday and hopefully make it up online for Thursday, we shall see. The data for this lab should be taken in your laboratory notebook from the video. To make these videos took about 21 hours of filming and another 18 hours of production work.
All lab session review the following videos:
- Grignard Reaction Part 1: Apparatus. This video is 22 minutes in length.
- Grignard Reaction Part 2: Reaction. This video is 33 minutes in length.
- Grignard Reaction Part 3: Isolation. This video is 44 minutes in length.
- Grignard Reaction Part 4: Characterization. This video is 22 minutes in length.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, February 4, 2021
After watching all of the Grignard lab videos it was time to turn our attention to writing the formal report. As well as looking at how to work-up the data from the lab, we also took in an in-depth look at all of the resources in the course that support you in writing the formal. We looked at each part of the formal report and broke down the requirements and what to focus on in your report on the Grignard reaction.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, February 9, 2021
This morning we decided to steal a little time from lab to work an problems from lecture. We worked the morning like a study session working the scheme and synthesis problems that were posted in Canvas for practice. Hopefully this session is helpful!
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, February 11, 2021
We started our look at the multistep synthesis of benzilic acid starting from benzaldehyde. This is a three step synthesis that will take us through some nice biological chemistry with a thiamine catalyst, some oxydation mechanisms, and finally through base catalyzed rearrangement. This project usually spans three to four weeks in the lab, and we'll digest it over several weeks as well. Today we take a look at the first reaction, the formation of benzoin from benzaldehyde. If you are looking for help with the Grignard formal report, we discussed more on the formal towards the end of the lecture.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, February 16, 2021
Today we covered the second reaction in the multistep synthesis of benzilic acid, the oxidation of benzoin to benzil. We are covering this reaction in anticipation of the lab videos that I hope to get up online for this weekend. Here we look at the oxidation step. We talk oxidation in general as well as specifically our nitric acid oxidation. We also look at the work-up for the reaction and the separation scheme. Both lab sessions lasted about an hour today.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, February 18, 2021
In today's lab period we stoll a little more time for some lecture practice to work synthesis problems. We pulled problems from those posted on Canvas and worked the various patterns.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, February 23, 2021
Today we covered the third reaction in the multistep synthesis, the reaction of benzil to benzilic acid. In this final reaction we look at the base catalyzed oxidation and rearrangement reaction that occurs. We discussed the reaction mechanism, the reaction methode, the work up, and a comparison of the characterizations of both benzil and benzilic acid. Now I just need to get the darn videos produced!
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, February 25, 2021
Having looked at all three reactions in the multistep synthesis of benzilic acid, today we went over the formal report. This was actually a really important lecture as we broke down the formal report and looked at each section and the focus and components that should be included in the formal. Watch this lecture before starting to write the formal for the multistep.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, March 2, 2021
We took it easy today while I'm still trying to catch up on editing the lab videos. Each session did something a little different today as I opened the floor to work on whatever people had questions on. The morning lab asked to go over the benzoin oxidation mechanism. From there we did a preview of the subject for today's lecture. We then previewed the next big topic we will cover in lecture - spectroscopy. We looked at what makes each form of spectroscopy different and how they are used together to decipher the structure of organic compounds. In the afternoon lab we talk more about the upcoming exam and the different problem types you are like to see on the exam. We did sample problems for each of these problem types. Regardless of which lab you are in, it might be good to watch both of these videos as they are each useful and completely different.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, March 4, 2021
We used today's lab time to support lecture by review old exam problems for exam one. Both morning and afternoon did essentially the same problems, however there were significant differences based on the follow-up questions that were asked. It might not be a bad idea to watch one section and skim through the other looking for those differences.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, March 16, 2021
Things are happening. While I'm still fighting back pain issues, I've made some positive improvements and we are getting back to work. It is still going to take me more time to process the rest of the videos for the multistep reaction. I just haven't been strong enough to takel that yet. Instead, what we did today is to take a look at a little more lecture material to support spectroscopy. We looked at chemical equivalence of both protons and carbons. The session today was approximately an hour where we looked at chemical equivalence. This is a critically important skill set for starting NMR.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, March 18, 2021
Second day on NMR. Today in lab we cover spin-spin coupling. We take a look at how neighboring protons cause splitting of signals in their near neighbors and the origin of how this splitting takes place. In the afternoon lab we did an example NMR problem from start to finish.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, March 30, 2021
We used lab time today to work on NMR. Specifically, we worked backwards from a molecule to the proposed spectrum breaking down the process stepwise. We worked from the number of chemical environments to the relative chemical shift expected for each, from there we added integration values, and finally we added the spin-spin coupling. We then used an NMR prediction software to verify our prediction. This is a required skill in solving NMR problems. If you cannot assess proposed structures then you cannot resolve structurally related compounds to find the correct structure. At the conclusion of this exercise each lab did a different NMR problem to its completion.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, April 1, 2021
Third day on NMR. Two good problems presented in the morning lab. I had to cancel the afternoon lab presentations as the vaccine monster caught up with me. Afternoon folks please watch the morning lab recording.
Morning Lab Session
Afternoon Lab Session please watch the morning lab session above.
- Lecture Date: Tuesday, April 6, 2021
The morning lab was cancelled this morning. In the afternoon lab we worked on individual questions from the group. The main question we looked at was looking at the numerous different substitution patterns that can occur on an aromatic ring system and how to recognize them. Towards the end of the lab we worked another problem start to finish.
Morning Lab Session - session cancelled
Afternoon Lab Session
- Lecture Date: Thursday, April 8, 2021
Second day on mass spectrometry. Today we used lab time to review some critical mass spec skills and to demonstrate some of the practice problems on Mass Spec tutorial from Linda Breci.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, April 13, 2021
As we get close to closing out the spectroscopy chapter, the one spectroscopy type that we have not covered yet is InfraRed Spectroscopy (IR). IR was covered in first semester. Zerubba covered IR in the course of first semester lab in Chem 12AL. I have a slightly different take on what to focus on in the IR spectrum than Zerubba. We both agree on the zones and interpretation, but I focus almost exclusively on zones 1 and 4. In this lab period we focus on the limits of IR and how to use it to best advantage with the other forms of spectroscopy to get the most info as fast as possible - Let's call it IR at a glance. Links to Zerubba's FTIR and my FTIR tabels are below as well.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, April 15, 2021
We did a great overview of fragmentation patters for mass spec this morning. We looked at more specific fragmentation patters for the most common functional groups. We also looked how to calculate and use the loss information in the spectrum to ascertain which functional groups may be present. In addition we did a harder NMR problem, actually an all-in-one problem using mass spec, IR and NMR to determine the structure of an unknown. This was a really fun problem and demonstrated some great problem solving skills and how to get overwhelmed in the middle of problem. This session was live in the morning lab and viewed asynchronously for the afternoon lab as I had an appointment for the afternoon.
Morning Lab Session
Afternoon Lab Session - please watch the lecture from this morning. This was a great sessions and there is a ton of good information in this lecture.
- Lecture Date: Tuesday, April 20, 2021
No lab lecture for today.
- Lecture Date: Thursday, April 22, 2021
So, I finally got tired of stealing time from lab for lecture. It's time that we start getting back into some lab concepts - in lab. So today we start taking a look at the Micheal-Aldol reaction. This experiment covers Experiment 64 in the 5th edition of Pavia and relates to experiment 37 and experiment 38. It's traditionally the last experiment performed in the curriculum before we move to special projects. I'll leave it to the video to describe the experiment in more detail and why I love this experiment, but suffice it to say that I'm looking forward to spending some time talking about this reaction and the challenges it presents.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, April 27, 2021
This was the second day on experiment 64 - The Michael-Aldo Experiment. Today we looked at how to scale the second part of the experiment. For this reaction we actually need to create a scaling factor. We discuss how to find and apply that scaling factor. We also discussed how the different substituents affect the reaction, either speeding it up or slowing it down, and different ways to compensate in order to make the reaction work.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, April 29, 2021
We used the lab time today as a study session for the lecture. This was a problem solving session involving Electrophilic Aromatic Substitution problems. Many different problem types were presented and lots of good discussion involving electronic and steric factors and which to use when.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Tuesday, May 4, 2021
Both morning and afternoon labs took some time to look at electrophilic addition to dienes and also spent some time on discussing the answer to quiz 5.
Morning Lab Session
Afternoon Lab Session
- Lecture Date: Thursday, May 6, 2021
Today was Diels-Alder day. We took on the Coop 4 Diels-Alder problems looking at intramolecular Diels-Alders reactions, and the issue of endo vs exo - when it matters and when it doesn't.
Morning Lab Session
Afternoon Lab Session
