CHM 3120 Assignment 1a 2009 final

CHM 3120 Assignment 1a 2009 final - CHM 3120 Assignment 1a...

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CHM 3120 Assignment 1a Fall 2009 1. Predict the product of the following reactions (include stereochemistry where appropriate). a) Ph O H EtMgBr THF b) O 1) NaBH 4 2) H 2 O c) O t Bu Ph Zn(BH 4 ) 2 d) O 1) NaBH 4 2) H 2 O e) Ph O SMe Zn(BH 4 ) 2 THF THF
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2. Provide the structure of the major product for each of the following sets of reaction conditions (include appropriate stereochemistry). Et CH 3 O OCH 3 CH 3 MgBr THF Zn(BH 4 ) 2 THF LiAlH 4 THF 3. Show how you would prepare the “syn” and “anti” isomers of the following molecule. Provide a retrosynthesis. (Hint: you will need two separate reactions with different starting materials). Ph OH CH 3 ?
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4. Predict the product(s) of the following reactions. a) b) c) N H O H H + (cat.) d) O N H CH 2 Br 1) 2) 3) H + /H 2 O H N O H + CH 3 I H N H + CH 3 I O + + 5. Consider the following unsymmetrical ketone. Draw the structures of the thermodynamic and kinetic enolates. What are the reaction conditions and factors that ensure the selective formation of each?
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CHM 3120 Assignment 1a 2009 final - CHM 3120 Assignment 1a...

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