Amber Patel Organic Chemistry Lab Section 004 1/27/2014 Melting Point Determination of Compounds and Compound Mixtures

Purpose: Determining the melting point of known solids and mixtures, and an unknown. Reagents: 1) Unknown number 7 provided by the instructor and unknown comparison chart. Compound Benzophenone Maleic anhydride 4-Nitrotoluene Naphthalene Acetanilide Benzoic acid Urea Salicyclic acid Sulfanilamide Succinic acid 3,5-Dinitrobenzoic acid p-Terphenyl Melting Point 49-51 52-54 54-56 80-82 113.5-114 121.5-122 132.5-133 158.5-159 165-166 184.5-185 205-211 210-211

2) Proportions of Mixtures to be tested: - Urea/Cinnamic acid proportions: 1:0, 1:4, 1:1, 4:1 and 0:1. Procedure: 1) Testing melting of Pure Urea and Cinnamic acid Crush the fine powder on a watch glass for both substances separately. Using a spatula put the fine powder into capillary to fill 2-3 mm of the capillary. Heat 20C below 132.5C and then slowly heat the capillary at 1C per minute. Mark the temperature at which the first drop appears and the last solid present for both the substances.

2) Testing mixtures of Urea and Cinnamic acid Approximate proportions of ratios 1 Urea: 4 cinnamic acid, 1 Urea: 1 Cinnamic acid and 4 Urea: 1 Cinnamic acid are made. The mixtures are crushed and filled in two capillaries to fill 2-3mm of the capillary. The first capillary is rapidly heated to find approximate temperature for the mixture. Then the second capillary is heated 20C below the approximate and then slowly heated at 1C per minute. The temperature at which the first drop appears and the last solid present for all the mixtures in noted. 3) Melting point of Unkown An unknown is obtained from instructor and crush it in a watch glass. Two capillaries are made for the unknown. The first capillary is rapidly heated to find approximate temperature for the mixture. Then the second capillary is heated 20C below the approximate and then slowly heated at 1C per minute. The temperature at which the first drop appears and the last solid present is noted. Experiment Setup: The experiment required the use of a digital melting point apparatus provided by instructor and capillaries. In the experiment the capillaries were first filled with the substances and then put into the digital thermometer where the amp rate, start temperature and final temperature could be set. The melting points were noted by looking through a magnifying glass in digital thermometer. Clean Up: All the capillaries should be safely disposed in broken glassware container and other waste mixtures and reagents should be disposed into hazardous containers. Observation: In the first part of the experiment when the capillaries for Urea and Cinnamic acid were heated to 20C below 132C there was no liquid present in the capillaries. The first drop was seen for both Urea and Cinnamic acid when they reached 132C and 132.2C respectively. In the second trial Urea melted slightly earlier at 131C than at 132C while Cinnamic acid stayed constant at 132.4C. The slight change was very small and thus can be disregarded. It was thus noted that these two different compounds have almost the same melting point ranges. In the second part of the experiment when the two mixtures were mixed it was noticed that the melting point for all three proportions tested had decreased and the range of melting point had also increased. For the third part the unknown was first heated rapidly and the approximate temperature for melting was found to be 120C. Then when it was slowly heated the melting point range of the unknown was found to be between 121.6C and 122.3C. When this melting point range was compared to the unknown charts it was found that the unknown provided by the instructor was Benzoic acid.

Data and Calculations: 1) Melting Point of Urea and Cinnamic acid #of trial Urea Cinnamic acid 1 2 132C-133C 131C -132.5C 132.2C-133.7C 132.4C -133.6C

2) Data for Mixtures Mixture proportion Urea:Cinnamic acid 100% Urea 1:4 1:1 4:1 100%Cinnamic acid Phase Diagram Melting Point 131C -132.5C 96.5C-115.9C 117.9C-118.9C 114C -116C 132.2C-133.6C

Phase diagram
140 120 Temprature 100 80 60 40 20 0 0 20 40 60 80 100 Percent of Cinnamic acid increasing while Urea decrasing 120

3) Data for Unknown Unknown 7 Fast approximate Slow Melting Point 120C 121C-122.3C

Conclusion: In the experiment for the first part of the experiment the melting points of Urea and Cinnamic acid were found to be approximately the same, which was similar to the known melting point for Urea and Cinnamic acid. In one trial the Urea temperature was slightly lower than the known this could just be due to human error while reading the thermometer or due to some impurity in the capillary as the melting point was depressed which is commonly seen when impurities are present. In the second part of the experiment it was noticed that 100 percent pure substances had higher temperatures and smaller range compared to mixtures of Urea and Cinnamic acid. The reason for this is in a mixture Urea acts as an impurity for Cinnamic acid and Cinnamic acid acts as an impurity for Urea. The depression in the melting point could be because Urea and Cinnamic acid have a different crystalline lattice form. This can cause the melting point to lower as the disruption in the crystalline form due to impurity causes the lattice to be broken down more easily at reduced temperatures as certain hydrogen or other forms of bonds are absent. The broadening of the melting point range can be explained, as the heat cannot be evenly distributed due to difference in crystalline structures of Urea and Benzoic acid. The phase diagram created for this experiment seems irregular as the 1:1 mixture of Urea and Cinnamic acid had a higher temperature than 1:4 and 4:1 ratio. This seems to be odd because in 1:1 ratio there is a more impurity (50 percent) suggesting the depression should be more than 4:1 or 1:4, which have lower impurity (25 Percent). The bad reading could be caused by a manual error in reading the capillary correctly or making the mixture. Due to the bad result for 1:1 mixture I drew a slope of the other two and tried to find a close estimate to the eutectic point to make the phase diagram look a normal. For the third part of the experiment the unknown was heated rapidly and the estimate temperature was noted as 120C while the actual temperature was 121.6C122.3C. The difference between the estimate and actual can be explained because in the first case the capillary was heated rapidly making the transfer of heat uneven in the lattice. The unknown when compared to unknown chart was found to be benzoic acid as the melting points were very close.