Triphenylmethyl Bromide Lab Report

Observations The purpose of this experiment was to be able to synthesize triphenylmethyl bromide from triphenylmethanol by a trityl carbocation intermediate. During the experiment, 0.100 g of triphenylmethanol was placed into a small test tube. The triphenylmethanol looked like a white powder. Next 2 mL of acetic acid was added to the test tube and the solution turned a cloudy white color. There was a strong odor similar to the smell of vinegar given off. After the solution was heated and the solid dissolved, 0.2 mL of hydrobromic acid was added to the test tube. The solution turned a bright yellow color after the hydrobromic acid was added. The solution was heated in a hot water bath for 5-10 minutes and then let cool. After heating, the

After adding the acetic acid and hydrobromic acid to the solution, and heating and recrystallizing the solution, the product triphenylmethyl bromide was created and had a mass of 0.103 g. The theoretical yield was calculated by determining the limiting reagent in the reaction. The triphenylmethanol was the limiting reagent in the reaction. The total amount of mass from the triphenylmethanol was converted to moles by using the molar mass of the triphenylmethanol. The amount of moles was then converted into grams to determine the theoretical yield, 0.125 g. The percent yield was then calculated by dividing the actual yield by the theoretical yield and multiplying the result by 100%. The percent yield was 82.4%. The melting point of the product was observed to be 139.5 °C. The theoretical yield of the product is 152 °C (University of South Carolina Department of Chemistry and Biochemistry). The melting point percent difference was calculated by subtracting the theoretical melting point from the actual melting point, dividing the result by the theoretical melting point, and multiplying the result by 100%. The melting point difference was 8.22%. Example calculations are shown

Since triphenylmethanol is a tertiary alcohol, it went through an SN1 reaction where a carbocation was formed in order for the covalent bond to form. Compared to SN2 reactions, SN1 reactions are composed of three steps with the carbocation in the rate determining step. An important every day example of an SN1 reaction is the digestion of carbohydrates by glycosidase. This is an SN1 reaction where water is the nucleophile and and an alcohol is the leaving group. Humans use this process to break down carbohydrates for an energy source. Other biological organisms use this same process such as cows that break down cellulose through an SN1