Links to download Zoom Lab Videos and PDF files
- Lecture Date: Monday, August 23, 2021
No Lab was planned for today.
- Lecture Date: Wednesday, August 25, 2021
In this first lab meeting we focused on an alkene problem to review the alkene chapter and assess the strength of the class. We did the first half of the problem set.
- Lecture Date: Monday, August 30, 2021
Today we focused on the second half of the alkene reaction problem set.
- Lecture Date: Wednesday, September 1, 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.
This first day is covering the reaction mechanism and how the reaction is performed. In subsequent classes we will go over issues that can arrise with the reaction and how to write a formal report for this lab. In the mean time you should watch the videos below that show the synthesis of triphenyl methanol taking place.
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.
Please 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.
Here is the recorded video from today and the notes taken during the lecture.
- Lecture Date: Wednesday, September 8, 2021
Today we continued with the pre-lab lecture for the Grignard reaction. We worked through the rest of the reaction and the work-up. We also took a look at the separation scheme for the reaction. The next step is for you to watch the four video lectures that are linked in the post from September 1 above.
- Lecture Date: Monday, September 13, 2021
Today we looked at formal reports. We reviewed the formal report guidelines that are online at ChemEd.Study as well as the formal report rubric. We also showed how all these resources are linked within the module on the canvas shell, in addition to a sample formal report from the Chem 12A lab, the formation of acetylsalicylic acid. In the second half of the lecture we looked at the scale of the chemical reaction, the way to calculate the percent yield of the reaction, and all the common problems that can arise during the reaction that can contribute to lower yields. Basically we showed all the things to watch for in the video that you can talk about in the formal.
- Lecture Date: Wednesday, September 15, 2021
Today we stole a bit of time from lab to use as a problem solving day. We worked a couple of problems from both the alkene problem set and the advanced problem set that are linked as practice in the canvas module.
- Lecture Date: Monday, September 20, 2021
In today's lecture we started by discussing the Grignard reaction and the emphasis for the introduction. We discussed focusing the introduction on both Grignard as the scientist and the generality of the Grignard reaction, and the importance of making new carbon-carbon bonds in synthesis. That importance is signified in compounds like Taxol - a chemotherapy drug that could not have been brought to market as a natural product, scientists needed to find a way to synthesize the molecule by total synthesis.
In the second half of the lecture we worked on more of the problems from the advanced alkene problem set that is posted in Canvas.
- Lecture Date: Wednesday, September 22, 2021
No lecture for today as I was tied up with a chemical waste pickup at Cabrillo.
- Lecture Date: Monday, September 27, 2021
Today we started our look at the multistep synthesis of benzilic acid from benzaldehyde. This is a three step reaction that starts with converting benzaldehyde to benzoin, oxidation of benzoin to benzil, and finally base catalyzed conversion of benzil to benzillic acid. In this lecture we cover the first reaction of the thiamine catalyzed conversion of benzaldehyde to benzoin.
- Lecture Date: Wednesday, September 29, 2021
We used the lab today as a problem solving session looking at synthesis involving alkene and alkyne reactions. The problems were all chosen to show a solid progression of skills. These are all excellent exam type questions and a required skill set for success in organic chemistry.
- Lecture Date: Monday, October 4, 2021
Today was a bit of a repeat from Wednesday where we worked on synthesis problems. We started the day by looking at common reaction patterns. We then used many of those reaction patterns in the problem sets.
- Lecture Date: Wednesday, October 6, 2021
One more day of synthesis problems. These problems are showing extended patterns that are very common starting from unfunctionalized alkanes to build alkenes, alkynes, alcohols and larger molecules with multiple functional groups.
- Lecture Date: Monday, October 11, 2021
This was one more day on synthesis problems. Much of the emphasis today was on the use of epoxides as versatile substrates for SN2 and E2 substrates.
- Lecture Date: Wednesday, October 13, 2021
We got back to a focus on lab today. In this lecture we look at the second reaction in the Multistep Synthesis of Benzilic Acid. The lecture covers the conversion of Benzoin to Benzil.
- Lecture Date: Monday, October 18, 2021
Lab was cancelled this morning. My recollection is that I had a migraine and took the morning off to recover.
- Lecture Date: Wednesday, October 20, 2021
We used the lab this morning to discuss problems from the exam. We used like open office hours. Students were allowed to ask questions and I tried to give direction without giving away the ball game. We worked for a little more than an hour at which point I stepped out and allowed students to collaborate.
- Lecture Date: Monday, October 25, 2021
We covered the third and last reaction in the Multistep Synthesis of Benzilic Acid, the synthesis of benzilic acid from benzil. In this lecture we look at the reaction mechanism, the reaction procedure and workup, as well as the characterization of the synthesized benzilic acid.
- Lecture Date: Wednesday, October 27, 2021
There was no lab lecture today
- Lecture Date: Monday, November 1, 2021
Today we did a segment on chemical equivalence for both 1H-NMR and 13C-NMR. We also took a look at using integration values within 1H-NMR to understand how many protons are in each chemical environment.
- Lecture Date: Monday, November 3, 2021
This morning is an NMR problem solving session. tools and techniques were presented for parsing the information in the NMR spectrums allowing for easy organization of utilization towards structure elucidation.
- Lecture Date: Monday, November 8, 2021
This morning we worked on NMR problems from the WebSpectra website. These were problems that were attempted by several students in the class last friday. Hopefully seeing these worked out was helpful. We completed numbers 3, 6, and 7.
- Lecture Date: Wednesday, November 10, 2021
This morning we worked on some specific skills in NMR. Specifically we looked at using the spin-spin coupling data to connect subgroups creating larger subgroups thereby giving fewer permeations in rebuilding the molecule. This is critical skill set for being able to solve NMR problems.
- Lecture Date: Monday, November 15, 2021
This was one last day on NMR skills.
- Lecture Date: Wednesday, November 17, 2021
Today we reviewed mass spectrometry concepts and problems.
- Lecture Date: Monday, November 22, 2021
Today we took a look at the coop problems for coop 3. The first problem we did start to finish using the spectroscopy rubric as a guide and check list. The first problem was a little more difficult than the second and third problems by virtue of having three fluorines that can not be seen by isotope effect. we also looked at problems two and three to give everyone a start on those two as well.
- Lecture Date: Wednesday, November 24, 2021
This was a mass spec day where we took a closer look at mass spec problems specifically for alcohols (I think). Better description coming later, I just really wanted to get this up before my travels back down to California.
- Lecture Date: Wednesday, November 29, 2021
The notes for today were very limited. We had just one question on Hard vs Soft ionization techniques for mass spec.
- Lecture Date: Wednesday, December 1, 2021
In this last lecture I made it clear that there will not be another formal report for the course. We will have only the one formal report for the Grignard reaction.
- audio only m4a file
- video with audio mp4 file
- No lecture notes were taken today