Daniel D.

Lee TA: Courtney Guenther CHEM 245-102 February 3rd, 2011 Lab Report #1 SOLIDS: Recrystallization and Melting Points Section 4: Results and Observations Melting Point Determination Mel-Temp apparatus #6, Correction:

Naphthalene (Sample A): Melting Ranges (°C) Trial #1 78.0 80.0 - (-1.0) (-1.0) 79.0 81.0°C Trial #2 77.0 80.0 - (-1.0) (-1.0) 78.0 81.0°C Both trials within 1°C, Benzil (Sample C): Melting Ranges (°C) Trial #1 91.0 95.0 - (-1.5) (-1.5) 92.5 96.5°C Trial #2 90.0 95.0 - (-1.5) (-1.5) 91.5 96.5°C Both trials within 1°C,

Mel-Temp apparatus #6 corrections Temperature Observed, corrected Mel-Temp apparatus #6 corrections Temperature Observed, corrected (True high melting point temperature: 81°C)

Mel-Temp apparatus #6 corrections Temperature Observed, corrected Mel-Temp apparatus #6 corrections Temperature Observed, corrected (True high melting point temperature: 94°C)

Cinnamic Acid (Sample D): Melting Ranges (°C) Trial #1 127.0 130.0 - (-1.5) (-1.5) Mel-Temp apparatus #6 corrections 128.5 131.5°C Temperature Observed, corrected Trial #2 128.0 130.0 - (-1.5) (-1.5) Mel-Temp apparatus #6 corrections 129.5 131.5°C Temperature Observed, corrected Both trials within 1°C, (True high melting point temperature: 132°C)

0 .0 149. corrected Sample O 149.5°C Temperature Observed.5) (-1.5 153.5) (-1.90 g Product Weight 0.5°C Temperature Observed. corrected .(when heating the impure benzoic acid with the necessary solution.5) Mel-Temp apparatus #6 corrections 150.5 152.After heating.0 Range . corrected Out of the 12 possible samples and according to their given upper end of melting ranges.5) (-1.5 . corrected Trial #2 149. the solution turns gray/dark. Recrystallization Benzoic acid Initial Weight 0.23g/0.5) (-1.(-1.0 151.0°C Temperature Observed.5) (-1.5 150.0 116.(-1.0°C Temperature Observed.5 .23 g Percent  Recovery   Benzoic Acid: (0. the observed melting point range of the unknown can either be adipid acid or benzenesulfonamide since their upper end of melting point range is around 150°C.5) Mel-Temp apparatus #6 corrections 129.0 151.(-1.5 137. corrected The melting point range of the mixed sample of vial O and the unknown reflects the initial melting point measurement of the unknown. Mixture-melting point determinations with adipid acid (Sample N) and benzenesulfonamide (Sample O): Melting Ranges (°C) Sample N 128.5 117.      .5°C Temperature Observed.5) Mel-Temp apparatus #6 corrections 113.0 (Preliminary) .(-1.5) Mel-Temp apparatus #6 corrections 150.90g)x100 = 25.0 135.(-1. the sample boiled out of the flask because the heat was set too high) potentially sample was lost .Unknown (Sample 119): Melting Ranges (°C) Trial #1 147.56 % Melting Point 112.5) Mel-Temp apparatus #6 corrections 148.

Because the measured values were greater than the actual melting point range for the benzil.5) Mel-Temp apparatus #6 corrections 108.(-1. and cinnamic acid.8 mm Hg At 0°C. and same for naphthalene. . and after hot filtration the solution became clear. -1°C At 100°C.06g)x100 = 40.23g o Turned the solution black.The product was clear/white powdery crystals.When added to boiling water. and both trials for each compound were less than 1°C off each other.0 113. For the observed melting ranges. I was able to practice using the Mel-Temp apparatus.Weight of decolorizing carbon: 0.06 g 0.0°C 757. the measured values were relatively close to the true values.5°C greater than the true temperature. the benzil s two trials both showed high melting temperature 2. benzil.78 % Melting Point 107.84g/2. we cannot conclude that the correction for the Melt-Temp apparatus is incorrect. For each case. Thermometer Calibration Temperature Observed from Iced Water Temperature Observed from Boiling Water Barometer Reading Corrections      1. they were close to that of the true temperature ranges: the naphthalene s two trials observed upper melting point matched that of the true value s. .5) (-1.0 Range . . corrected .0°C 98.5 114. the resulting sample is a very clear blue solution.5°C Temperature Observed. it solidifies pretty quickly into white powdery figures Acetanilide Initial Weight Product Weight Percent Recovery 2.84 g    Benzoic Acid: (0. less than for the cinnamic acid. and cinnamic acids both trials showed values that were 0.- As the sample cools down. +2°C Section 5: Conclusions Melting Point Determination In obtaining the melting points of naphthalene.5°C less than that of the true values.

the range of the observed is a bit too large. then subtract 1°C to correct it because the actual temperature is probably 0°C. the melting ranges came out to be 148. As for the percent recovery. 150°C and 151 respectively.23 g while the initial weight was 0. This may have also been due to the filtration process that was not able to completely purify the sample. If the temperature is observed to be 98°C. the observed 113. and indicating that the unknown sample be one of them. On the other hand. the vague visual cues.5-150. The percent recovery was 40. for which the two possible samples were each mixed with the unknown in approximately equal proportions to get the melting ranges of the mixed samples. possibly due to improper folding of the fluted filter paper or maybe the crystallized sample was not cleanly washed enough with cold solvent right after the vacuum filtration to wash away the soluble impurities that may have been with the wetness of the product. However.5-117.5-114.5-114. less than when the unknown was measured previously. which is far greater than the ideal 2°C range. The percent recovery was 25.5°C range is pretty low. add 2°C to correct it because the actual temperature is probably 100°C. the product weight was 0. As for the thermometer calibration. having lost too much of the desired sample during the process. compared to the true upper melting range of acetanilide of 114. the two upper melting range is very close.rather.5-137.90 g.5-153. may have been the cause for the small deviations. the mix of the benzenesulfonamide and the unknown had a melting range (150.5°C. The hot gravity filtration process may have let some impure solutes to pass the filter paper.5°C. The percent recovery of the experiment indicates that a fair amount of the original sample was able to recrystallize and to purify to become products. Even though 25.3°C with the observed 108. subtract -2. reflecting the upper end of melting ranges of adipic acid and benzenesulfonamide. if the temperature from this specific thermometer is observed to be 1°C.06g and the product weight was 0.5°C. the experiment is considered unsuccessful. Therefore.56% is not within this unfavorable range.56% ad the melting range of the product was 113. subtract 1.5-117. considering how the true upper melting range of benzoic acid is 122°C. if it is less than around 20%. Also.84g. Then. to get the actual temperature. the initial weight of the sample was 2. Technically speaking. the melting range of adipid acid and the unknown was 129.0°C. As for the acetanilide. it is possible that determining when melting actually ended for each compound.5°C and 150. Measuring the melting range for Unknown 119. at 0°C. This may have been due to products lost during filtrations or may have been due to it spilling over when it was boiling at the beginning of the experiment. it can be concluded that the unknown sample 119 was benzenesulfonamide since is it generally the case that impurity decreases the melting point of a pure solid. Also. Recrystallization For recrystallizing the impure benzoic acid. at 100°C. .5°C. indicating some sort of impurity or error in measurement of the melting range via the Mel-Temp apparatus. it is still pretty close to it.78% and the melting range of the product was 108. with the mixture-melting point process.0°C) that was consistent with the unknown s individual measurement.5-152.

which would have soluble impurities that need to be washed with fresh cold solvent before drying. Using excessive amounts of solvent decreases the recovery of the solute because it will waste time in boiling off later in the process and if too much solvent is used for cooling later on after filtration. it will also absorb some of the desired products if too much of the decolorizing carbon is used.004 g to be the amount of unrecoverable by virtue of its solubility at 0°C. e) Crystals are obtained by breaking up the solidified mass of an oil that originally separated from the hot solution. If the hot flask is immediately placed in an ice-water bath.9 grams of benzoic acid was recrystallized from 20 mL of water.212 g to be the amount of unrecoverable by virtue of its solubility at 0°C. Also. Therefore. the oil crystallizes. b) The crystals obtained after filtration are not washed with fresh cold solvent before drying. . obtaining crystals from breaking up the solidified mass of an oil that originally separated from the hot solution is not preferable.06 grams of acetanilide was recrystallized from 40 mL of water. the crystals may still have solvent or water pockets that were able to stay with the crystals. a. if the solution is not cooled slowly. With solubility of 0. With solubility of 0. 0. That oil will probably contain some impurities. f) Crystallization is accelerated by immediately placing the flask of hot solution in an ice-water bath. Even though it is able to suck up impurities. More solvent means more of the solutes will stay dissolved. The extra fresh cold solvent will allow for the sample to become purer by washing away the soluble impurities that may be present after filtration because the crystals are not completely dry yet. however. a. we expect 0. a. a. because the oil was part of the solution before separating. it may result in rapid recrystallization of small crystals that may trap impurities. the flask may shatter. a.53 g per 100 mL at 0°C. eventually leading to a lost of the desired product. After boiling off. For the acetanilide. it is likely that the oil dissolved some of the solvent and impurities there within. a. When the separated oil cool down. 2. If the crystals are washed with fresh hot solvent.53g/100mL = x g/40mL Exercise 23) a) In the solution step. Calculations for benzoic acid: 0. c) The crystals referred to in (b) are washed with fresh hot solvent. little or no solutes crystallizes out. we expect 0. the crystals are in danger of being dissolved again.02 g per 100 mL at 0°C.Section 6: Answers to Assigned Questions Exercise 20) For the benzoic acid. d) A large quantity of decolorizing carbon is used. an unnecessarily large volume of solvent is used.02g/100mL = x g/20mL Calculations for acetanilide: 0.

d) 162. .5°C melting range indicates a pure sample as the range is only within 1°C.5-163. The sample that again results in the melting range around 160°C will indicate that the unknown is the same as the sample mixed with it in the mixture.Exercise 14) a) Melting range of about 2°C is considered normal and pure. it is also decomposition while melting. By mixing the pure samples of the three possibilities with the unknown in equal proportions. indicating some sort of impurity. the 147°C (dec) not only is not in the format of melting ranges. the melting ranges of the mixed samples will be measured using the Mel-Temp apparatus. the melting point is lowered as a result. c) 46-60°C melting range would be considered very impure as the range of 14°C is far greater than the ideal 2°C range. it is inferred that the sample is impure. The other two samples will probably have melting ranges that are less than the previously observed 160°C. Therefore. Exercise 16) Mixture-melting point procedure will use the pure samples to identify the unknown. unless it is a mixed sample at its eutectic point which is a rare phenomenon. b) Because the sample decomposed while melting. In this case.

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