W03 problems5b key

W03 problems5b key - Problem Set 5 5. Propose T W O ( 2 )...

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Br H O 2. HCN 3. OMs Li Cu H H O Me OH Br H I Problem Set 5 (Chapter 15.1-15.2 Organometallic Reagents Ch 16.1-16.7 Aldehyde/Ketone I) TA: Danny Ng 2/10/2003 2. Provide the r e a g e n t s or p r o d u c t s for the following reactions. Pay attention to stereochemistry if applicable. 1. Provide the structures for the following compounds. Pay attention to stereochemistry if applicable. a) tert -butyl propyl ketone b) 4 R -acetyl-1-phenyl-pentanone c) 2,2-dibenzoyl-heptanal d) 4,4-dimethyl-cyclohex-2-enone a) 1. Mg, ether 2. b) c) d) 1. PCC e) 1. Li, ether 2. CuI 3. H 3 O + 1. NaNH 2 2. 3. H 3 O + O O O H O O Ph Ph O O OH OH H OH H OH OH NC CN HO H
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I Br O PPh 3 PPh 3 Ph 3 P Li O Ph 3 P O PPh 3 PPh 3 PPh 3 O O Ph 3 P OH OH O OH Ph 3 P O O Ph 3 P TA: Danny Ng 2/10/2003 Problem Set 5 f) g) h) 1. (Sia) 2 BH 2. H 2 O 2 , NaOH i) 3. Provide a mechanism for the following reaction. a) 1. PPh 3 2. NaNH 2 3. 1. O 3 2. DMS 3. (2 equiv.) 4. H 3 O + j) 1. 2. H 2 , Pd 1. Mg, ether 2. 3. H 3 O + OH OH OH OH OH OH R S R R S S S R
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O Ph 3 P O PPh 3 Br O Ph Ph Ph Ph Br Br O H O HO OH NC Br HO O H H HO Ph Ph HO OH NC TA: Danny Ng 2/10/2003
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Unformatted text preview: Problem Set 5 5. Propose T W O ( 2 ) ways to make the following compound, both using the W i t t i g R e a c t i o n . 4. Propose a synthesis for each of the following compounds using B r o m o c y c l o h e x a n e as the starting material. 1. Mg 2. 3. H + 1. PPh 3 2. NaNH 2 3. 1. Mg 2. 3. H + (racemic) 1. Mg 2. 3. H + 4. PCC 5. HCN Na OH O O O MgBr O O H O H O BrMg O BrMg O TA: Danny Ng 2/10/2003 Problem Set 5 6. Propose FOUR(4) different syntheses for the following compound based on each of the given disconnections below (no further disconnections necessary). (a) (b)(c) (d) Disconnection (a): Disconnection (b): Disconnection (c): Disconnection (d): Target Target Target Target Target...
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W03 problems5b key - Problem Set 5 5. Propose T W O ( 2 )...

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