ORGANIC CHEMISTRY I LABORATORY 220L-Tue 1-4pm

Lab #2 Melting Point Determination

Kathleen Swanson 10/08/2013

INTRODUCTION: A pure organic solid compound has many consistent and predictable physical properties that can be used to characterize a sample. Some of these include molecular weight, boiling point, refractive index, density and melting point (Williamson, 2011). The melting point of a compound is the temperature at which the vapor pressure is equal to the pressure of the liquid. This characteristic melting point, specific and static to each organic solid compound, can be used to indicate the purity of a sample since a pure sample will consistently demonstrate the same narrow melting point range (within 1-2 C) over many trials. This knowledge of a directly proportional relationship between purity and melting point temperature allows us to determine the purity of a sample, even when unknown; as the degree of impurity decreases, the range of melting point temperatures attributed to the sample will both decrease and also displace the entire range upward (Williamson, 2011). Recrystallization of a sample removes impurities that are dissociated in a solvent, while the sample recrystallizes as it is cooled. This process, and subsequent determination of the melting point of the sample, should coincide with an observable narrowing of the melting point range and a complete upward displacement of the range. This process can be continued until a point at which no further narrowing or upward displacement is observe, and is the point at which a sample can be referred to as pure.

This laboratory exercise seeks to both identify an unknown organic sample via melting point determination, while also demonstrating the characteristic relationship between the purity of this sample and the range of melting point temperatures associated with it. The melting point, and range of a sample thought to contain some minor impurities, is compared to the same sample which underwent a recrystallization process intended to remove these impurities. The degree of change observed in the range of melting point temperatures and any displacement noted will confirm whether or not the recrystallization processes did in fact remove potential impurities from the raw sample obtain from the Chemistry Laboratory storage of organic compounds.

Materials and Methods:

The Mel-Temp apparatus which consists of an electrically heated aluminum block is used to heat the sample which is contained within a thing glass capillary. This glass capillary is magnified and viewable through an exterior port. Observation of the sample and its phase change from solid to liquid is conducted through this 6x powered lens. A mercury thermometer is staged so that its reported temperature can be assumed to match that of the sampled contained within the glass capillary. The

aluminum plate temperature is increased 1C per minute until the solid begins to show signs of liquefying. This point marks the beginning, or lower bound of the melting point range. The upper boundary of the melting point range is marked by the temperature at which the entire sample is completely liquefied. The same process is conducted with the recrystallized, presume pure sample.

Compounds used: 1.) an organic solid compound that underwent the recrystallization process one week prior to melting point determinations
2.)

as well as a presumed impure, sample of the same material; used for comparison as previously noted.

Experimental:
Compound Melting Point Temp lower boundary 120C 121C 124C 124C +3.5C (124C-120.5C) Melting Point Temp Upper boundary 125C 124C 126C 126C +1.5C (126C-124.5C) Narrowed, -2) (avg4C-2C) Melting Point Range 5C 3C 2C 2C Melting Point (mean of the range) 122.5C 122.5C 125C 125C +2.5C

T1: impure sample T2: impure sample

(Trial 2)

T1: Pure sample

(recrystallized)

T2: Pure Sample

(recrystallized) MP Range/Mean displacement (impure v. pure) Difference in MP Range Impure v. pure

Table 1: data collected from 2 trials, for each an impure organic sample and a pure, recrystallized organic sample. With melting point range, mean value, difference between means (impure v. pure), and displacement of range and mean (impure v. pure); T1 = Trial 1; T2 =Trial 2 TABLE OF PHYSICAL PROPERTIES:
MW Compound (g/mol) (g/mL) (mL) (g) Skin/eye irritant, hazard Benzoic Acid 122.12 g/mole .1 gram 8.19 x mol for inhalation and ingestion Density Vol. Mass mole Hazard

Table 2: properties of unknown sample later identified as benzoic acid.

Discussion:

Based upon literature reviewed, it was predicted that the recrystallization and subsequent purification of an organic solid sample would alter the intrinsic properties of the sample (that was previously presumed to contain impurities), as evidenced by observable changes in melting point and melting point range. Given an organic compounds melting point is predictable and reproducible it was expected that either the addition of, or extraction of impurities would alter this otherwise static property and would be quantifiable upon comparison. Recrystallized, pure organic sample was expected to possess a more narrow range of temperatures associated with its melting point, in addition to observing an upward displacement of the entire melting point temperature range. These features (displacement and narrowing of the range) should also reveal the degree to which the original sample contained impurities. Or conversely results could illuminate possible errors made in the previous recrystallization process if the impurities were thought to have persisted into the pure sample.

Both the impure and pure samples were subjected to two trials of heat application at a rate of 1C per minute. The melting point upper and lower bounds were recorded and compared to test earlier predictions. The data showed a clear, observable narrowing in the range of melting point temperatures by 2C (calculated from the average of trials 1 and 2 for the impure sample). Results also showed a well define upward displacement in the entire range, with the lower bound increasing 3.5C, the upper bound increased 1.5C, as well as the mean melting point temperature which increased by 2.5C. The data confirms the predictions and shows that the recrystallization process performed a week earlier did in fact purify the sample. The melting point temperature of the purified organic compound was used to positively identify the unknown compound as benzoic acid (Table 3.2 Melting Point Unknowns, Williamson 2011)

Resources

Macroscale and Microscale Organic Experiments, Williamson, K.L., 2nd Edition. D.C. Health and Company