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Khalsa SCH 4U Mar. 2, 2013

Organic Chemistry Reactions Lab Report

PURPOSE: Part One: Alkene Bromine Water Addition Test: To test for the presence of alkenes using bromine water. Part Two: Alkenes & Oxidation: To test the presence of alkenes through oxidation using potassium permanganate reagent. Part Three: Oxidation of Alcohols With Potassium Permanganate: To observe the relative reaction rate when alcohols are oxidized using potassium permanganate reagent and sodium hydroxide catalyst. Part Four: Alcohols Reacted With Sodium Metal: To observe the relative reaction rate of alcohols with sodium metal. APPARATUS: Safety goggles Small test tube rack Medium test tube rack Sixteen small test tubes Nine medium-sized test tubes Sixteen 00-sized rubber stoppers Nine 1-sized rubber stoppers Fume hood Nederman Arm Two 1000ml beakers for liquid waste and rubber stoppers Pencil Paper Sink Wire test tube scrubber Tongs Paper towels Knife Plastic cutting board Five long glass pipette droppers

MATERIALS: Note: all bottles listed after cyclohexene should have a dropper as a lid. Bottle of pentane Bottle of hexane Bottle of 1-hexene Bottle of cyclohexane Bottle of cyclohexene Bottle of Br2 bromine water Bottle of potassium permanganate Bottle of methyl alcohol Bottle of ethyl alcohol Bottle of propyl alcohol Bottle of isopropyl alcohol PROCEDURE: Part One: Alkene Bromine Water Addition Test 1. 2. 3. Safety goggles were put on. A small test tube rack was obtained, and four small test tubes were aligned in one row, each facing up. Under the fume hood, the four bottles of alkanes and alkenes were arranged in order of the substances on page 1 of the Organic Chemistry observation package included. These bottles were pentane, hexane, cyclohexane and cyclohexene in that order. Note: These four substances were tested by the students. 1-hexene was tested by the teacher, and 1-pentene and toluene were not tested. 4. With the test tube rack in the fume hood, the following was done in the fume hood. A pipette bulb was placed in the pentane bottle. It was squeezed and let Bottle of butyl alcohol Bottle of isobutyl alcohol Bottle of secbutyl alcohol Bottle of t-butyl alcohol Bottle of sodium hydroxide catalyst A small chunk of sodium metal Bottle of acetone (for cleaning) water

go of once (while in the pentane), so that 30 drops were placed in the bulb. The pentane in the bulb was then squeezed into the first test tube in the test tube rack. A small rubber stopper was then placed on the test tube. 5. 6. 7. Step four was repeated for the three remaining substances. With the test tube rack and bromine water on a table, it was made sure of that the Nederman arm was above the table, and sucking air. The rubber stopper on the pentane test tube was removed. It was made sure of that this test tube was under the Nederman arm for the following part of this step. Six drops of bromine water were added to the test tube. The rubber stopper was placed on the test tube, and the results of the addition of substances were recorded. 8. 9. 10. 11. The pentane test tube was shaken, and results were then recorded after the shake. After a couple minutes, the results were recorded again. Step 7-9 were repeated for the three remaining substances in the test tube rack. The test tube rack was then placed under the fume hood. The two 1000ml beakers for waste and a cleaning bottle of acetone were also placed in the fume hood. 12. In one hand, two test tubes were grabbed, and the rubber stoppers of those were dropped in the 1000ml used rubber stoppers beaker. The substances within the test tubes were then dumped in the 1000ml liquid waste beaker. 13. With the test tubes facing at roughly a 45 to 90 degree angle with the ground, the acetone was squirted in the test tubes in a rotating fashion, so as to get it in all parts of the test tube. The remaining substance was poured into the liquid waste beaker until it looked like it was relatively clean. The test tubes were then placed back on the test tube rack, facing down. 14. 15. 16. Step 13 was repeated until all of the test tubes used were cleaned. The test tube rack was then put back on the shelf from which it came, and one then washed their hands. Safety goggles were put away.

Part Two: Potassium Permanganate Oxidation Test Of Alkenes 1. 2. 3. Safety goggles were put on. A small test tube rack was obtained, and four small test tubes were aligned in one row, each facing up. Under the fume hood, the four bottles of alkanes and alkenes were arranged in order of the substances on page 2 of the Organic Chemistry observation package included. These bottles were pentane, hexane, cyclohexane and cyclohexene in that order. Note: These four substances were tested by the students. 1-hexene was tested by the teacher, and 1-pentene and toluene were not tested. 4. With the test tube rack in the fume hood, the following was done in the fume hood. A pipette bulb was placed in the pentane bottle. It was squeezed and let go of once (while in the pentane), so that 30 drops were placed in the bulb. The pentane in the bulb was then squeezed into the first test tube in the test tube rack. A small rubber stopper was then placed on the test tube. 5. 6. Step four was repeated for the three remaining substances. With the test tube rack, bromine water and potassium permanganate on a table, it was made sure of that the Nederman arm was above the table, and sucking air. 7. The rubber stopper on the pentane test tube was removed. It was made sure of that this test tube was under the Nederman arm for the following part of this step. Six drops of potassium permanganate was added to the test tube, and six drops of bromine water were also added to the test tube. The rubber stopper was placed on the test tube, and the results of the addition of substances were recorded. 8. 9. 10. The pentane test tube was shaken, and results were then recorded after the shake. After a couple minutes, the results were recorded again. Step 7-9 were repeated for the three remaining substances in the test tube rack.

11.

The test tube rack was then placed under the fume hood. The two 1000ml beakers for waste and a cleaning bottle of acetone were also placed in the fume hood.

12.

In one hand, two test tubes were grabbed, and the rubber stoppers of those were dropped in the 1000ml used rubber stoppers beaker. The substances within the test tubes were then dumped in the 1000ml liquid waste beaker.

13.

With the test tubes facing at roughly a 45 to 90 degree angle with the ground, the acetone was squirted in the test tubes in a rotating fashion, so as to get it in all parts of the test tube. The remaining substance was poured into the liquid waste beaker until it looked like it was relatively clean. The test tubes were then placed back on the test tube rack, facing down.

14. 15. 16.

Step 13 was repeated until all of the test tubes used were cleaned. The test tube rack was then put back on the shelf from which it came, and one then washed their hands. Safety goggles were put away.

Part Three: Oxidation of Alcohols with Potassium Permanganate 1. 2. 3. Safety goggles were put on. A small test tube rack was obtained, and sixteen small test tubes were aligned in one two rows of eight, each facing up, on a table. All eight alcohols were aligned in order of substance on page 3 of the Organic Chemistry observation package included, on the same table as the previous step. 4. Thirty drops of methyl alcohol was added to the first test tube on each row of the rack. This was repeated for the other alcohols and test tubes until all test tubes had been filled. 5. 16 rubber stoppers, a bottle of potassium permanganate, a bottle of sodium hydroxide and the test tube rack were placed on a table. It was made sure of that the Nederman arm was above the table, and sucking air.

6. 7.

Six drops of sodium hydroxide were placed in each test tube of the second row of alcohols. Six drops of potassium permanganate were placed in each of the two test tubes in the first column on the rack. The rubber stoppers were then placed on each test tube in the first column, and observations were then recorded.

8. 9. 10.

Both of the previous test tubes shaken, and results were then recorded after the shake. Step 7-8 were repeated for all remaining columns of substances in the test tube rack. The test tube rack was then placed under the fume hood. The two 1000ml beakers for waste and a cleaning bottle of acetone were also placed in the fume hood.

11.

In one hand, two test tubes were grabbed, and the rubber stoppers of those were dropped in the 1000ml used rubber stoppers beaker. The substances within the test tubes were then dumped in the 1000ml liquid waste beaker.

12.

With the test tubes facing at roughly a 45 to 90 degree angle with the ground, the acetone was squirted in the test tubes in a rotating fashion, so as to get it in all parts of the test tube. The remaining substance was poured into the liquid waste beaker until it looked like it was relatively clean. The test tubes were then placed back on the test tube rack, facing down.

13. 14.

Step 13 was repeated until all of the test tubes used were relatively clean of liquid substance. The test tube rack was then placed under a sink. Using a wire test tube scrubber, each test tube was scrubbed while being rinsed by water, until all test tubes looked clean.

15. 16.

The test tube rack was then put back on the shelf from which it came, and one then washed their hands. Safety goggles were put away.

Part Four: Reaction of Alcohols with Sodium Metal

Note: This particular procedure was performed by the teacher. 1. 2. 3. Safety goggles were put on. A medium-sized test tube rack and nine medium-sized test tubes were acquired and placed on a table. The nine test tubes were aligned in one row. All eight alcohols were aligned in order of substance on page 3 of the Organic Chemistry observation package included. Nine 1-sized rubber stoppers were placed in the top of each test tube. 4. 5. Thirty drops of water was added to the first test tube. Thirty drops of methyl alcohol was added to the second test tube on each row of the rack. This was repeated for the other alcohols and test tubes until all test tubes had been filled. 6. Using tongs, a small (roughly 1 cm wide by 0.3 cm tall) chunk of sodium metal was removed from its bottled container and placed on the plastic cutting board. It was then cleaned off with a paper towel, and cut into nine even pieces. 7. 8. 9. 10. 11. 12. OBSERVATIONS: See included Organic Chemistry observation package. CONCLUSIONS: See included hand-written pages. The rubber stoppers were taken off of all test tubes. One of the nine chunks of sodium was added to the water through the use of tongs. The reaction was observed but not recorded. One of the eight remaining pieces of sodium was added to the methyl alcohol. The results were recorded. Step nine was repeated for all other alcohols in test tubes. The products of each reaction were disposed of and cleaned by the teacher. Safety goggles were put away.