Lab Manual- Experiment 6

Lab Manual- Experiment 6 - 8/26/2010 Experiment 6: Miscible...

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8/26/2010 E x p er i m e n t 6: M i s c ibl e I m m i s c ibl e L iq u id s A n d T h e S y n t h e s i s O f N y l on BACKGROUND READING: The actual synthesis done at the end of this experiment is one that may not be covered in your organic lecture course. However, the product that you will make is one that you probably encounter on a daily basis. All the background information you need to perform the experiment is given in this handout and in the assigned readings - Essay on Polymers and Plastics in Pavia (Page 371-400) and Experiment 47B, page 385-387; Solomons & Fryhle page 867-871; Wade page 1232-1233. INTRODUCTION: This experiment will be conducted in five parts during the course of one laboratory period. You will do your work in pairs. In the last part of the experiment, you and your lab partner will get to make nylon, a synthetic polymer commonly used in clothing, stockings, and certain plastics. Before you perform the nylon synthesis, you will do some investigations that will help you learn more about the solvents needed for your reaction. Nylon is an example of a condensation polymer. It is made industrially by the reaction of adipic acid with 1,6-hexanediamine as shown in Scheme 1. Notice that water molecules are formed as a byproduct of this reaction, which is why this reaction is referred to as condensation reaction. The reaction must be carried out at high temperatures and high pressures in order for the water to be driven off in the last step. Scheme 1.
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8/26/2010 In this experiment, adipoyl chloride will be used instead of adipic acid, in the reaction with 1,6- hexanediamine to form Nylon 6-6, as is shown in Scheme 2. This reaction is much faster than the reaction between adipic acid and 1,6-hexanediamine; it does not form an intermediate salt and does not require heating or elevated pressure, so it is much simpler to do in the lab. The small molecule released in this reaction is HCl, instead of H 2 O. Only one part of the Nylon 6-6 polymer is shown in brackets. This part is referred to as the repeat unit. The whole polymer is made up of many of these repeat units strung together. The total number of units in the polymer is n, formed when n molecules of 1,6-hexane-diamine react with n molecules of adipoyl chloride. Scheme 2. In this reaction, 1,6-hexanediamine is always dissolved in water while adipoyl chloride is always dissolved in an organic solvent. In Part III of the experiment, you will do miscibility tests on 6 organic liquids in order to select three of the following types of solvents for your nylon synthesis: one that is miscible with water; one that is immiscible with but less dense than water, and one that is immiscible with but more dense than water. When two liquids are immiscible, the only place where their molecules come in contact with each
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This note was uploaded on 10/27/2010 for the course CHEM 223 taught by Professor Hardin during the Fall '10 term at CUNY Hunter.

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Lab Manual- Experiment 6 - 8/26/2010 Experiment 6: Miscible...

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