Lab Manual- Experiment 8

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

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E x p er i m e n t 8: NUC LE O P H ILI C S U B S TIT U TI O N AN D I R S P E C T R OS C O P Y R e f e r e n ce s : Technique 7 (pages 608-629) ; Technique 12 (pages 681-708) ; Technique 25 (IR Spectroscopy), pages 851-886 in Pavia, Solomons & Fryhle, Chapter 2; Wade, Chapter 12. Also study the chapter on nucleophilic substitution in your lecture textbook carefully - Solomons & Fryhle, Chapter 6; Wade, pages 225-251. E X P E R I M E N T A L O V E R V IE W: For this experiment we will carry out Experiments 19 in Pavia (pages 158-161) and Procedures 8A and 8B described below. 8A a n d 8B a r e m i cr o s c a l e m o di f i c a t i o n s of t h e m a cr o s c a l e e x p er i m e n t s 20A a n d 20 B , w hi c h a r e d e s cr ib e d i n P a v i a on p ag e s 163 t h r o u gh 169. Y ou w il l f o ll ow t h e p r o ce du r e d e s cr ib e d i n t hi s h a nd o u t , w hi c h o nl y u s e s s in g l e nu c l e o phil e s in s t e ad of a m i x t u r e of c o m p e t i t i ve nu c l e o phil e s . The theory remains the same. In addition, your starting materials and products for 8A and 8B will be analyzed using Infrared (IR) spectroscopy instead of Gas Chromatography. This technique is described in Pavia on pages 851-886. It will also be discussed in the Recitation. You will obtain IR spectra under the guidance of your lab instructor for both the starting materials used and the products formed in procedures 8A and 8B. The presence or absence of characteristic peaks in the IR spectrum will help you to determine whether or not the reaction works and has gone to completion. Experiment 19 consists of a series of short test-tube reactions and the reaction time for 8B is only about ten minutes, not including the workup and isolation of the product, but Procedures 8A is longer, requiring a 75-minute reflux period. Procedures 8A and 8B also require IR analysis of both the starting materials and the products. Two weeks are provided for the completion of this entire procedure but you should plan your work efficiently so that you will be assured of finishing all parts. You should definitely have enough time to complete 8A and perform IR analysis of the product during the first lab session. If you still have more time, you may begin the test tube reactions as well. If you run short of time, then both sets of test tube reactions can easily be done along with Procedure 8B during the following week. Again, ALWAYS PLAN YOUR WORK IN DETAIL so that you can complete your experiments properly and in an efficient manner. ================================================================== Procedure 8A and 8B ( Exp. 20) use hot, concentrated H 2 SO 4 . USE GREAT CARE! ================================================================== 1
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Lab Manual- Experiment 8 - 8/26/2010 Experiment 8:...

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