3580 Spring 2011_PSET 12

3580 Spring 2011_PSET 12 - Chemistry 3580 Spring 2011...

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Chemistry 3580 Spring 2011 Prof. William Dichtel Homework: Problem Set #12 Will not be collected; key will be posted on 5/02/11 Textbook Problems: Ch 23 (p 1158) 23.40 (all except e), 23.44, 23.46, 23.49 (all except c&d) 23.51, 23.59 (b,c,f,g,h), 23.72b, Ch 24 (p 1213) 24.37a, 24.38, 24.43, 24.50 (1) Propose an efficient synthetic route to convert the starting material into the product. (2) Predict the products of the following transformations. OH H N Br N OEt O O H N O OH OH HO HO HO H 2 O Mixture of stereoisomers O HO HO O HO OH O HO OH HO OH H 3 O + Draw all hexafuranose monosaccharides that result from this hydrolysis reaction
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(5) Which of these amines could have been synthesized by reductive amination? Draw one possible set of starting materials for each of these amines. (3) Explain the following observations N H Compound A and compound B have very similar bond angles and shapes. Why does compound B have two separable stereoisomers
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3580 Spring 2011_PSET 12 - Chemistry 3580 Spring 2011...

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