Bromination Of Trans-Cinnamic Acid And Trans-Stilbene.

An Erlenmeyer flask was used to accommodate the largest volume of recrystallization solvent calculated and was cooled in an ice bath to increase the yield of crystals. The solid was collected by vacuum filtration and washed with a small amount of ice water. The product is then dried to a constant mass by use of an oven and weighed. A small amount of the unknown was compared to two samples of acetanilide and phenacetin for a melting point range to determine the identity. The temperature of the unknown was recorded when the first trace of liquid can be seen and when the unknown was completely liquid.

After each of the solids were completely dry, each was placed into a MelTemp device. The temperature at which each solid began to melt and completed melting was recorded.

During recrystallization, the solution was to be cooled to room temperature before placing it in an ice bath. Doing this allows enough time for the crystals to be formed because as the temperature decreases, the rate of crystallization slows down. If the solution was placed in the ice bath too quickly, then the cold would have blocked out the impurities and trapped them in the solution. The more impurities present, the lower the melting point so data would have been inaccurate. Also, if the melting point apparatus wasn’t set up correctly, the data would have been imprecise.

What is the stereochemistry for the bromination of trans-cinnamic acid, and how is it formed?

These were most likely impurities, in which case I added a bit more water than was necessary. Also, the lab manual says to take two samples of each mixture (unknown; ½ phenacetin; ½ acetanilide) for the melting point, but we only conducted one.

The vial was removed from the heat and cooled to room temperature. The spin vane was rinsed with 2-3 drops of warm water over the conical vial. The vial was cooled to room temperature then placed in an ice bath for 15 minutes. The liquid was decanted from the mixture and the resulting crystals were dried on filter paper. The crystals were then placed on a watch glass for further drying. The crystals were weighed and a small sample was placed into a capillary tube for melting point determination.

4- chlorobenzoic acid which was the aqueous layer has a theoretical melting point of 240-243°C, the organic layer, 4-chlorobenzyl alcohol has a theoretical melting point of 68-71°C. During our experiment we were unable to collect any data for the organic

Through our data acquisition on day one our predicted values for the change in temperature of our NaCl solution in water was slightly off. This was most likely due to recording the freezing temperature sometime after the precise moment of the solution freezing. However, we predicted that as we doubled our concentration of NaCl in solution the freezing point depression would also double which is consistent with our results. Through our day one experiments we were able to better understand the ability of NaCl as a deicer by understanding how the freezing point depression changes based on concentration. We could further test these results by testing with different concentrations of NaCl.

No correction had to be made to the melting points because the standard melted in the range labeled on the bottle. The melted point observed is the correct melting point.

The freezing point depression constant for water that was experimentally determined in this analysis was 0.0479 °C/m, which was derived from the slope of the trend line in Figure 4. This is significantly lower than the constant stated in the literature of 1.86 °C/m.1 The freezing point temperature determined via cryoscopy should have been much lower in the high sucrose concentration solutions.

Purpose: The purpose of this experiment is to observe a variety of chemical reactions and to identify patterns in the conversion of reactants into products.

The solvolysis of t-butyl bromide is an SN1 reaction, or a first order nucleophilic substitution reaction. An SN1 reaction involves a nucleophilic attack on an electrophilic substrate. The reaction is SN1 because there is steric obstruction on the electrophile, bromine is a good leaving group due to its large size and low electronegativity, a stable tertiary carbocation is formed, and a weak nucleophile is formed. Since a strong acid, HBr, is formed as a byproduct of this reaction, SN1 dominates over E1. The first step in an SN1 reaction is the formation of a highly reactive carbocation, in which a leaving group is ejected. The ionization to form a carbocation is the rate limiting step of an SN1 reaction, as it is highly endothermic and has a large activation energy. The subsequent nucleophilic attack by solvent and deprotonation is fast and does not contribute to the rate law for the reaction. The Hammond Postulate predicts that the transition state for any process is most similar to the higher energy species, and is more affected by changes to the free energy of the higher energy species. Thus, the reaction rate for the solvolysis of t-butyl bromide is unimolecular and entirely dependent on the initial concentration of t-butyl bromide.

Tube 4 now should only have crude solid in the tube and it is then weighed. The tube is placed into a 50℃ water bath and then approximately 0.5 -1 ml of methanol is added, as well as H2O until the solution gets cloudy, once the solution is dissolved it is cooled to room temperature and then iced. The crystals are then collected using a Hirsh funnel. Next a small amount (~ 0.1g) of the crystals are placed into a melting point tube and placed into the melting point machine to record the unknown neutral substances melting point.

Discussion: As seen in the melting point determination, the average melting point range of the product was 172.2-185.3ºC. The melting points of the possible products are listed as 101ºC for o-methoxybenzoic acid, 110ºC for m- methoxybenzoic acid, and 185ºC for p- methoxybenzoic acid. As the melting point of the sample

The first involved aliquotting 10µl of each of the reconstituted materials into cryovials (in triplicate) and were then stored upright and frozen at -20oC immediately . On a test day, 1490µl Premier diluent was added to each of the thawed materials (1:150 dilution ratio as per manufacturer’s instructions)