To install StudyMoose App tap and then “Add to Home Screen”
Save to my list
Remove from my list
In this experimental procedure, Benzpinacolone was synthesized through a two-step process. Initially, benzophenone underwent photoreduction in 2-propanol, utilizing sunlight to absorb UV rays and facilitate the reaction. The subsequent step involved dehydrating benzpinacol to benzpinacolone, achieved by subjecting benzpinacol to acid-catalyzed rearrangement through the addition of iodine and acetic acid. The reaction involved refluxing, cooling, filtration, and washing with ethanol. The resulting percent yield was 71%, although challenges such as prolonged photoreduction and product loss during transfer contributed to a lower than expected yield.
The observed melting point was slightly lower than the theoretical value, attributed to potential impurities. Various spectroscopic analyses, including IR spectra for benzophenone and 1H NMR, 13C NMR, and IR spectra for benzpinacol and benzpinacolone, were conducted to identify functional groups and compare the compounds.
This experiment focused on utilizing ultraviolet light for the photoreduction of benzophenone and employing carbocation reaction conditions to induce the benzpinacol rearrangement. The absorption of UV light elevated the organic compounds to electronically excited states, enabling reactions that typically do not occur in their ground state.
In Part 1, the reduction of benzophenone was carried out, driven by the UV radiation it absorbs, in the presence of 2-propanol. The resulting product, benzpinacol, underwent a subsequent reaction with iodine in acetic acid to produce benzpinacolone through rearrangement.
Procedure:
Part 1: Photoreduction of Benzophenone This experiment necessitates an irradiation period of at least 24 hours.
Part 2: Dehydration of Benzpinacol to Benzpinacolone.
Introduce 3.0g of benzpinacol and heat the solution slowly until it gently boils.
Observations: Part 1:
Part 2:
Flow Chart: A flow chart details the stepwise progression of both Part 1 and Part 2 of the experiment.
Table of Reagents: A comprehensive table lists the molecular weight, density, melting point, boiling point, and concentration for the various compounds involved in the experiment.
Results (Data/Calculations included): Part 1:
Part 2:
Calculations: The calculations involve finding the limiting reagent, theoretical yield, and percent yield for Benzpinacolone.
Results (Continued): Benzpinacolone was obtained with a 71% yield, and its observed melting point was close to the theoretical value, indicating a successful reaction. The physical properties of the product, such as color, crystal size, and smell, were noted.
Synthesis of Benzpinacolone: Photoreduction and Dehydration Processes with Spectroscopic Analysis. (2024, Feb 28). Retrieved from https://studymoose.com/document/synthesis-of-benzpinacolone-photoreduction-and-dehydration-processes-with-spectroscopic-analysis
👋 Hi! I’m your smart assistant Amy!
Don’t know where to start? Type your requirements and I’ll connect you to an academic expert within 3 minutes.
get help with your assignment