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Quiz 6 - 2a for example by using Newman or Sawhorse...

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CHM 2123, Quiz #6: Oxidation and Reduction Posted: November 4, 2010 Due: November 8, 2010 before 4pm Name: Student #: Name of your TA: Section : example : Tuesday, 8h30 1. Oxidation and reduction processes are very important, both in the laboratory and in living systems. In the lab, it is essential to analyse these reactions unambiguously. Please show in the space below how you could analyze the oxidation of p -nitrobenzyl alcohol using each of the following techniques. Be precise on what you should observe when comparing the alcohol, the aldehyde and the carboxylic acid using each technique. a) Thin layer chromatography. Please show (qualitatively) the expected polarity for each product. (1 point) b) Infrared spectroscopy. (2 points) c) 1 H NMR spectroscopy (2 points)
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2. During the second part of the experiment, you will perform a stereoselective reaction favoring the formation of a meso compound. Clearly illustrate the tridimensional structure of the meso isomer ( 2b ) and of each enantiomer (
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Unformatted text preview: 2a ), for example by using Newman or Sawhorse projections. (1.5 points) 3. At the end of the reduction using NaBH 4 , you will add crushed ice, followed by water and 1 mL of 3M HCl (DROPWISE). During this last step, gas evolution will occur and an emulsion will form. a) Which gas is formed during the addition of HCl? Show your reasoning using a short mechanism using the unreacted B-H bonds and HCl. (1 point) b) What is the boron byproduct formed using acid hydrolysis? (0.5 point) 4. There is an important note at the end of experiment #6: you will use the diol formed in a subsequent reaction the following week (experiment #7). It will be important to have a diol that is relatively dry for performing experiment #7 and a possible approach is described in the laboratory manual. However, there are many other ways to obtain a dry solid organic compound. Please briefly describe one below (concept and/or experimental procedure). (1 point)...
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Quiz 6 - 2a for example by using Newman or Sawhorse...

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