Final Summary: Development of a Novel Grignard Experiment

Hi all,

I am officially done with my research for the summer. I made a lot of progress, to the point where a few labs could be made from the work that I have done. Even though I have a total of 11 working experiments, they don’t line up like Dr. Lashley and I would like for the W&M undergraduate labs. For this reason I’ll continue my work into next semester.

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Update #3: Development of a Novel Grignard Lab

Hi all,

We’re nearing the end of my time in the lab this summer and things are going pretty well. My professor is excited about the work that I’ve done and believes we’re right on the cusp of being finished with this. Right now, I have a total of 10 working reactions
(which was the goal). 2 of these reactions are slower so I would like to replace them, if we can. For the next 2 weeks, I’ll be finishing the lab by testing a few more unknowns then beginning to write a procedure for the students.

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Update #2: Development of a Novel Grignard Experiment

Hi all,

My project has hit some speed bumps along the way but I think we’re getting somewhere. I believe that I’ll have to redesign my lab in order to finish it this semester and prepare it for implementation in the upcoming fall semester. Originally, I planned on having 4 Grignard reagents and 4 ketones. Now, I plan on using 2 Grignard reagents with 5-6 ketones, which will still allow for each group to have a unique product. The main reason for the switch is the reactivity of my reagents. When I tested bromonaphthalene and bromotoluene, they took too long to react fully. The low reactivity with the magnesium makes them unusable for the short Organic II labs. Upon further research into Grignard reagents, the 2 I happened to start with are among the most reactive. Because of this, I’ll work around the 2 very reactive reagents.

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Update #1: Development of a Novel Grignard Reaction Lab

Hi all,

Abstract: http://ccsummerresearch.blogs.wm.edu/author/mssmith01/

During the past week and a half, I have tested out two new grignard reagents. The first one was benzyl bromide. Because of its high reactivity, the benzene derivative was very quick to react with the magnesium. On the flip side, it was also very quick to react with itself, creating a lot of byproduct. Although I expected this it affects the procedure of the lab because the newly formed product must be used quickly. The longer it is left to reflux, the more byproduct there will be. One solution has been very low heat when refluxing. Another possible way to get around this is to use benzyl chloride. Benzyl chloride will still react with the magnesium but it will most likely be slower because it is less reactive compared to benzyl bromide. Although I have yet to try all the ketones with benzyl bromide, so far it’s promising.

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Development of a Novel Grignard Reaction Lab

Hi everyone,

I’m Matt Smith and my research involves the development of a new organic chemistry experiment for W&M labs. The research will focus on the Nobel-prize winning Grignard reaction, where a carbon nucleophile is created to attack a carbonyl as shown in the image below. This reaction will create a tertiary alcohol. A unique aspect to this lab is the creation of the tertiary alcohol with multiple unknown starting materials. By providing a student with 2 unknowns, they will be able to complete an experiment without knowing the product, as with real world research labs. Because of limitations in lab size and time, the alcohols created will need to be solid, allowing the students to determine their product with melting point. Students may also be provided with NMRs of their product to ensure they identify the proper alcohol.

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