Chem 210- W07exam3Key - I(25 points Name Page 1 Complete...

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Name _______________________ Page 1 I. (25 points) Complete the following reactions as directed. Transformations requiring sequential experimental steps should be numbered appropriately. Show the major organic product(s) unless otherwise specified. Abbreviations for reagents are not allowed. If a product forms as a s t e r e o i s o m e r i c m i x t u r e , draw one and write "+enantiomer" or "+diastereomer" in the box. NOTE: all stereocenters should be drawn unambiguously - show the positions of all atoms or groups at each of these sites. D. C 7 H 6 Describe the product(s): (check the best answer - no partial credit) OsO 4 A racemic mixture of products would form A single unique product would form A mixture of 2 diastereomeric products would form A mixture of 4 stereoisomeric products would form Both regioisomers and stereoisomers would form A. 1. B 2 H 6 2. NaOH/H 2 O 2 B. C. H 2 SO 4 (cat) O 3 1. 2. CH 3 SCH 3 x connectivity stereo 1 H-NMR signals: 2 (3:1) 13 C-NMR signals: 2 1 H-NMR signals: 1 13 C-NMR signals:1 H H H H OH OH + diastereomer Draw ALL organic products in the appropriate boxes: C C O O H H O C H H O O C O H H H H H 2 Pd/BaSO 4 PbO + CH 3 CH 3 CH 2 CH 3 CH 3 H 2 Pt OH + diastereomer H 2 O CH 3 CH 3 OH H + enantiomer 3 3 4 4 4 3 4
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CH 3 Name _______________________ Page 2 II. (25 points) Predict the product(s) in each of the following reactions. Draw a l l products, etc. that fulfill the requirements given in the answer box; be sure to show any stereochemistry clearly. (no partial) O I O product(s) having molecular formula C 7 H 13 Br CH 3 CH 2 ONa CH 3 CH 2 OH OH H 3 C H H HBr C H 3 C O O O H product(s) having the following spectroscopic data: 13 C-NMR signals: 4 1 H-NMR signals: 3 (1:2:3) H H H H 3 C Br H Br H 3 C H H can be drawn flat, too Br H 3 C
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