Grignard Reaction: Synthesis Of Triphenylmethanol
Grignard Reaction: Synthesis of Triphenylmethanol
Dominic DiRaimo
Lab Partners:
Roxana Hernandez
Somata Thach
TA: Sreya Mukherjee
December 5, 2013
Introduction
Grignard reagents are good nucleophiles as well as strong bases (Weldegirma). It allows compounds to react with acidic compounds, therefor is must be free from acids as well as water during the desired reaction. Another important aspect of Grignard reagent is that refluxing is necessary to carry out the reaction (Weldegirma). The reagent has been studied for a very long time period. As early as the 1920’s, Grignard reagents could be identified and studied qualitatively by a color test. For a very
long, the importance of this compound was understood and studied. For example, in the 1980’s, new innovative techniques were being discovered using the reagent to use practically on certain nucleophiles. These reactions have been studied for ages and are vital to all of organic chemistry. (Science Spot)
Mechanism
-------Mg-------> ----1) Ph2C=O----> Et2O 2) H+
Table of Chemicals
Bromobenzene Phenyl MgBr Triphenylmethanol Diethyl Ether
MP: -31C MP: n/a MP: 162C MP:-116C
Hazards: All chemicals can cause severe skin, eyes, nose, throat, and/or lung irritation.
(New Jersey Department of Health)
Results
Melting Point: 163°C
Appearance: Clumped together yellow crystals
Percent Yield %Yield = [(wt of product) / (wt of crude)] X 100% %Yield = [(0.001) / (0.027)] X 100% %Yield = (0.037) X 100% %Yield = 3.7%
Discussion The results that were obtained were fairy good. The percent yield of the final product could have definitely been better, however, all of the results such as the melting point and appearance of the product were in line with that of the literature. The most likely cause of this loss of product was that it was so purified that some of the product was lost during the purification product. The melting point results back up this theory. The aprotic solvent was used because it is important and vital to the reaction and reaction time. Aprotic solvents do not react with strong bases, as used in this experiment. Therefore, the solvent would not change or affect the reaction. Overall, the experiment data turned out excellently and the product was easily confirmed.
Conclusion
The information in this experiment revealed that it was successful in that the results were very similar to the given literature values, regardless of the percent yield. The techniques which were used in this experiment can be used in many of the other experiments. Vacuum filtration for example has been used in several experiments in the past, and will be used again in future experiments. The experiment did accomplish what it was set out to do because the goals were completed accordingly.
References
Experimental Organic Chemistry Lab Manual, S. Weldegirma, USF Chemistry Department
New Jersey Department of Health Website
Science Spot Website, T. Trimpe, 2009
Dominic DiRaimo
Lab Partners:
Roxana Hernandez
Somata Thach
TA: Sreya Mukherjee
December 5, 2013
Introduction
Grignard reagents are good nucleophiles as well as strong bases (Weldegirma). It allows compounds to react with acidic compounds, therefor is must be free from acids as well as water during the desired reaction. Another important aspect of Grignard reagent is that refluxing is necessary to carry out the reaction (Weldegirma). The reagent has been studied for a very long time period. As early as the 1920’s, Grignard reagents could be identified and studied qualitatively by a color test. For a very
long, the importance of this compound was understood and studied. For example, in the 1980’s, new innovative techniques were being discovered using the reagent to use practically on certain nucleophiles. These reactions have been studied for ages and are vital to all of organic chemistry. (Science Spot)
Mechanism
-------Mg-------> ----1) Ph2C=O----> Et2O 2) H+
Table of Chemicals
Bromobenzene Phenyl MgBr Triphenylmethanol Diethyl Ether
MP: -31C MP: n/a MP: 162C MP:-116C
Hazards: All chemicals can cause severe skin, eyes, nose, throat, and/or lung irritation.
(New Jersey Department of Health)
Results
Melting Point: 163°C
Appearance: Clumped together yellow crystals
Percent Yield %Yield = [(wt of product) / (wt of crude)] X 100% %Yield = [(0.001) / (0.027)] X 100% %Yield = (0.037) X 100% %Yield = 3.7%
Discussion The results that were obtained were fairy good. The percent yield of the final product could have definitely been better, however, all of the results such as the melting point and appearance of the product were in line with that of the literature. The most likely cause of this loss of product was that it was so purified that some of the product was lost during the purification product. The melting point results back up this theory. The aprotic solvent was used because it is important and vital to the reaction and reaction time. Aprotic solvents do not react with strong bases, as used in this experiment. Therefore, the solvent would not change or affect the reaction. Overall, the experiment data turned out excellently and the product was easily confirmed.
Conclusion
The information in this experiment revealed that it was successful in that the results were very similar to the given literature values, regardless of the percent yield. The techniques which were used in this experiment can be used in many of the other experiments. Vacuum filtration for example has been used in several experiments in the past, and will be used again in future experiments. The experiment did accomplish what it was set out to do because the goals were completed accordingly.
References
Experimental Organic Chemistry Lab Manual, S. Weldegirma, USF Chemistry Department
New Jersey Department of Health Website
Science Spot Website, T. Trimpe, 2009