Essay about Nitration of Methyl Benzoate

Mayo, D. W.; Pike, R. M.; Forbes, D. C. Microscale Organic Laboratory with Multistep and Multiscale Syntheses, 5th ed.; John Wiley & Sons, Inc., 2011; pp 132-135.

8. ISBN: 0-558-05245-2 Virtual ChemLab: General Chemistry, Student Lab Manual/Workbook, V. 2.5, Third Edition, by Brian F. Woodfield and

6. Purpose: to clarify the mechanism for the cycloaddition reaction between benzonitrile oxide and an alkene, and to test the regiochemistry of the reaction between benzonitrile oxide and styrene; to purify the crude product of either trans-stilbene, cis-stilbene, or styrene reaction.

The objective of this lab was to create a ketone through an oxidation reaction using a using a secondary alcohol and oxidizing agent in order to use that ketone in a reduction reaction with a specific reducing agent to determine the affect of that reducing agent on the diastereoselectivity of the product. In the first part of this experiment, 4-tert-butylcyclohexanol was reacted with NaOCl, an oxidizing agent, and acetic acid to form 4-tert-butylcyclohexanone. In the second part of this experiment, 4-tert-butylcyclohexanone was reacted with a reducing agent, either NaBH4 in EtOH or Al(OiPr)3 in iPrOH, to form the product 4-tert-butylcyclohexanol. 1H NMR spectroscopy was used to determine the cis:trans ratio of the OH relative to the tert-butyl group in the product formed from the reduction reaction with each reducing agent. Thin-layer chromatography was used in both the oxidation and reduction steps to ensure that each reaction ran to completion.

The hydrobenzoin (meso) product of the benzil was isolated through the techniques of recrystallization and vacuum filtration. Because there NaBH4 was the limiting reagent in the experiment, 0.005604moles of NaBH4 should yield 1.2008g of hydrobenzoin (meso). The mass of the isolated product was 0.613g, resulting in a 51.1% yield. There are many reasons to account for the loss of 48.9% of

Fifield, F. W. and Kealey, D. 1995. Principles and Practice of Analytical chemistry. (4th ed) Glasgow, Blackie Academic and professional.

After the initial mixture has refluxed, 9.11 grams of benzophenone was dissolved in 100 mL of anhydrous ether in a beaker and was then transferred into the separatory on the reflux apparatus. This solution was then added to the Grignard reagent at a drop wise rate while stirring. After the benzophenone was added, the mixture was then refluxed for 15 minutes on a heating mantle.

Dictionary of organic compounds, 6th edition, Chapman and Hall, London, Volume 3(& Volume 6), 1996 Maria Lindsay and Sean P. Hickey, Organic chemistry lab 2 manual, department of Chemistry University of New Orleans

Abstract: This procedure demonstrates the nitration of methyl benzoate to prepare methyl m-nitrobenzoate. Methyl benzoate was treated with concentrated Nitric and Sulfuric acid to yield methyl m-nitrobenzoate. The product was then isolated and recrystallized using methanol. This reaction is an example of an electrophilic aromatic substitution reaction, in which the nitro group replaces a proton of the aromatic ring. Following recrystallization, melting point and infrared were used to identify and characterize the product of the reaction.

Gilbert, John and Stephen F. Martin. Experiment Organic Chemistry: A Miniscale & Microscale Approach. Belmont, CA: Thomson Brooks/Cole, 2010. 537-547. Print.

The properties were first discovered in the 1980s by a Cuban biologist, Misael Bordier Chibas. Misael was studying the affects of poisons on different aliments, when he

Adrain, A. L (1997). The Most Important Thing I Know. New York, NY: MJF Books.

This experiment was designed by conducting a substitution reaction to construct a complex compound (2-methylphenoxyacetic acid) from two simple parts; also known as synthesis - converting simple molecules into more complex molecules. A purification technique known as crystallization was used to purify the product. Suction filtration was used to filter out the product. The experiment was completed over a three-day experimental period.

“Chemist Collector Bader Donates RBW Notebook” is an article written by Theodor Benfey. This article was published in Newsmagazine of the Chemical Heritage Foundation, Volume 19, Number 4 Winter 2001/2. It can be found on pages 16 through 17. Alfred Bader was an ambitious graduate student at Harvard University. He attended a lecture course that was given by Robert Burns Woodward. Woodward was a distinguished chemist, also known for his artistic skills that display both the elegance of his organic syntheses and in the way he depicted them in his lectures. Although Bader didn’t do his graduate work with a different professor, his exposure to Woodward—a distinguished chemist of that time period—led to great accomplishments. This includes establishing

Although organic reactions have been conducted by man since the discovery of fire, the science of Organic chemistry did not develop until the turn of the eighteenth century, mainly in France at first, then in Germany, later on in England. By far the largest variety of materials that bombard us are made up of organic elements. The beginning of the Ninetieth century was also the dawn of chemistry, all organic substances were understood