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Anissa Garza Organic Chemistry II Lab Dr. Panthi 03 February 2020

Nothing but Nylon Abstract The purpose of this experiment is to create polymerization reaction by joining together two small monomers to create one larger molecule. The end product of this experiment is nylon that is created by using a six carbon diamine and a derivative of a ten carbon dicarboxylic acid.

Introduction During this experiment two small organic monomers are used to create a synthetic polymer. The process of polymerization occurs when an amino acid from one monomer attaches and links to a carboxylic acid from the other monomer. This creates an amide linkage that leaves the functional groups of the monomers available for further reactions.

Materials Chemicals

Apparatus

- 10 ml of 1,6-hexanediamine/NaOH - 25 mL of a 0.2 M decanedioyl chloride hexane -water to rinse nylon

-2-150mL beaker -gradulated cylinder -wire with hook

Experimental Procedure Instead of the 25mL that the lab initially called for 10mL of the 1,6 hexanediamine/NaOH was measured in a gradulated cylinder. The 10mL of 1,6 hexanediamine/NaOH was added to a 150mL beaker and set aside. Colored green dye was added during this step of the experiment to the 0.5M 1,6 hexanediamine/NaOH. The 25mL of 0.2M solution of decanedioyl chloride in hexane was measured in a gradulated cylinder. It was then added to the 150mL beaker that contained 1,6 hexanediamine/NaOH. It was poured carefully into the 150mL beaker in order to not disturb the aqueous diamine layer. The metal paper clip with a hook was used to reach in between the layers and grasp the nylon that was formed. Carefully ,without breaking the nylon forming, the nylon was wrapped around the outside of a clean 150mL beaker. The number of times the nylon was wrapped around the beaker was recorded for later calculations. The nylon was then washed, drained and weighed. The length was multiplied by the circumference of the beeaker times the number of turns recorded. Wastes were disposed of properly in the waste area.

Results and Calculations

Discussion When calculating the theoretical yield there can be different reasons why the theoretical yield could be off. For example, not all of the nylon from the beaker would have been accounted for in the experiment. There could have been some left behind. Another way an error could occur is if the water used to wash the nylon has not been dried up causing it to weigh more than it should.

Conclusion In conclusion the percentage yield was calculated to be 5.01%. The theoretical yield of the reagent was calculated to be 1.594g.

Post Lab Questions

1. Describe a safety hazard associated with this lab and what you did to prevent it from being a problem. A safety hazard that our group avoided during the experiment was when the nylon was being wrapped around the beaker some of the chemicals were still on the nylon rope. In order to protect our hands from the chemicals transporting we wore gloves.

2. What is the purpose of the NaOH used in the reaction to make nylon from a diacyl chloride? The purpose of NaOH is to maintain the pH of the solution. It also acts to keep the amine in the form of a nucleophile. 3. Why do the methylene chloride and hexane solutions form two layers? (Are hexane and methylene chloride immiscible? Try it!) They are both miscible because they are nonpolar and like dissolve like. 4. Why can’t you calculate the yield of nylon in moles (the usual unit used for % yield)? You can't calculate the yield of nylon in moles because there is not enough time to dry to product fully. 5. For industrial nylon manufacturing, would you use the di-acid or the di-acyl chloride? Why? Acyl chlorides are much more reactive, so you would use the diacyl chloride....