Experiment 55: Qualitative Analysis

Morgan Lepley

Organic Chemistry Lab, CHEM 369 University of Tennessee, Knoxville Bo Meng Dr. Laureta Smith Date Preformed: 28 July 2011 Date Due: 1 August 2011

Introduction: The purpose of this lab was to prove the identity of an unknown organic compound by performing various tests and using process of elimination. After obtaining our unknown, we were asked to determine the boiling point or melting point using distillation or the mel-temp. Once the boiling point or melting point has been obtained, we were able to eliminate some compounds. A solubility test then needs to be done to further eliminate groups. Then, we tested for aldehydes, ketones, aromaticity, carboxylic acids, phenols, and alcohols to determine the functional group. After the functional group was confirmed, specific test were done within each functional group to further analyze the unknown compound. After these test have been complete, the IR, H-NMR, and C-NMR were used to further confirmed the identity of the unknown. Procedure Outline: The physical features of the unknown were recorded. Then the boiling point was taken using simple distillation. 20mL of the unknown was placed in a round bottom flask and kept at a medium boil until all of the unknown had been distilled. A solubility test was then performed using five different test tubes containing 1 mL of water, 5% NaOH, 5% HCL, 5% NaHCO3, and concentrated H2SO4 and 2-3 drops of the unknown compound. Then the IR spectrum was used to determining key functional groups. An alcohol group and C-O bond was present on the IR. An unsaturation test was used to test for carboxylic acid or ketone group. Five drops of bromine, 1 mL methylene chloride with 4 drops of the unknown liquid was used for the test. If the liquid turns clear the test is positive. Then an alcohol test was used to

prove the presence of an alcohol. The acetyl chloride test was used. In a test tube, 0.25 mL of unknown and 2 drops of acetyl chloride were added. Gas evolved and turned blue litmus paper red, indicating positive results for this test. Once the presence of an alcohol was confirmed a test for 1, 2, or 3 was needed. 0.5mL of lucas reagent and 2-3 drops of the unknown were placed in a test tube and shaken vigorously. No reaction took place, indicating that the unknown was a 1 alcohol. The C-NMR and H-NMR were then used to identify the amount of carbons and hydrogens present in the chain. Data: Name Water Sodium Hydroxide Hydrochloric Acid Sodium Bicarbonate Sulfuric Acid 1-Hexanol Bromine Methylene Chloride Acetyl Chloride Br CH2Cl2 CH3COCl Structure H2O NaOH HCl NaHCO3 H2SO4 Role Solvent Solvent Solvent Solvent Solvent Unknown Solvent Solvent Solvent IR Spectrum Peak (cm-1) 3600-3200 ~2900 & 2800 1480 1050 Bond Vibration R-OH C-H Stretch Scissor Bend C-O (1 Alcohol) Amount Used 1 mL 1 mL 1 mL 1 mL 1 mL 5 drops 1 mL 2 drops Hazards Corrosive Corrisive Irritant Corrosive Irritant Corrosive Irritant Corrosive

1H-NMR

Chemical Shift (ppm) 0.95 1.4 1.6 1.8 3.6

13C-NMR

Integration 3H 6H 2H 1H 2H

Chemical Shift (ppm) 15. 8 22.5 24.9 32.0 33.0 63.5 Results and Discussion:

Multiplicity Quartet Triplet Triplet Triplet Triplet Triplet

Initially, the physical properties of the unknown were recorded. The compounded was a clear liquid, whose odor resembled alcohol. The boiling point, determined by simple distillation to be 151-154 C. Following this miscibility tests were done, which revealed the compound to be any of the following functional groups: alkenes, alkynes, alcohols, ketones, aldehydes, esters, ethers, or amides. After this, a unsaturation test was preformed. The result of this test was negative eliminating every group except alcohol. After it was determined that the functional group was an alcohol, tests were done to confirmed that fact an alcohol was present. The acetyl chloride test evolved acidic gas confirming the presence of an alcohol. A lucas reagent test was then done to test for 1, 2, or 3. There was no reaction indicating it was a 1 alcohol. Using all this information, determining the identity of the unknown was easy. After the

miscibility test and the alcohol tests were done it was obvious the compound had to be a primary alcohol. The boiling point of the unknown was 151-154C. The molecule with the closest boiling point was 1-hexanol, with a boiling point of 157C. Finally, the IR spectrum, H-NMR, and C-NMR confirmed the identity of the unknown. The broad peak around 3600-3200 confirmed the presence of an alcohol. The peak at 1050 also confirmed the presence of a primary C-O stretch. The H-NMR showed 5 different hydrogens. The most deshielded hydrogen at 3.6. This corresponds to the two hydrogens on the carbon directly next to the electronegative oxygen. The most shielded hydrogens are on the carbon farthest away from the oxygen. There are overlapping multiplets around 1.4 ppm that correspond to the interactions between the hydrogen of the alkyl chain. In the C-NMR there are six different carbons present. The most deshielded carbon is the one next to the alcohol group and the most shielded carbon is the one farthest away. This experiment was done in order to gain understanding on how running various tests can reveal the identity of an unknown compound. Through planning out a procedure to follow, experience was gained on how to plan an experiment that could later be used for real-life scenarios. Through the tests performed and analysis of the IR spectrum, H-NMR, and C-NMR the identity of the compound was found to be 1- hexanol. Conclusion: The experiment was preformed in order to gain knowledge and understanding about the way chemists go about identifying unknown compounds. The experiment was successful in teaching the process of the way qualitative

analysis is done. After the results had been analyzed, the identity of the unknown was determined to be 1-hexanol. Overall, this experiment was good practice for the procedure done in professional lab work and organic chemistry labs. References: Pavia, Donald L., Gary M. Lampman, George S. Kriz, and Randall G. Engel. A Smallscale Approach to Organic Laboratory Techniques. 3rd ed. Belmont, CA: Brooks/Cole ; Cengage Learning, 2011. Print.