radical_problems - propagation steps O ROOR SO 2 Cl S Cl...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003, S. Tabacco± Optional Problem Set 8: Radicals 1. Please provide a detailed mechanism for the formation of each of the illustrated products.± H O Me Me Me Me Me Me O Me t- t- Bu cat. BuO–O 100 °C 2. The decarbonylation of the two labeled pentenals shown below has been studied. O D D ROOR H H Me D D D D Dilute Solution 1 : 1 Concentrated Solution 1 : 1.5 D O ROOR± D Me Me Dilute Solution 1 : 1 Concentrated Solution 1 : 1.4 a) Please provide a mechanism for the formation of each of the four products. b) For each reaction, explain the effect of the concentration on the product distribution. 3. Please provide a mechanism for the illustrated reaction. Show the initiation and
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Unformatted text preview: propagation steps. O ROOR SO 2 Cl S Cl HCl ∆ O 4. Please provide a mechanism for the formation of each product, and rationalize the predominant formation of A . O cat. t-BuO–O Bu Ph O Ph O Me Me Ph O Me 120 °C O O Me major minor A B 5. Please provide a mechanism for the illustrated transformation. O Br O O OMe H n-Bu 3 OMe SnH AIBN, ∆ OH 6. Identify A and B , and provide a mechanism for their formation. O C 6 H 4 Cl 3 NS N S O CCl 4 AIBN, ∆ C 4 H 7 Cl CO 2 A B (3 vinyl H's in 1 H NMR) 7. Please provide a mechanism for the illustrated transformation. catalytic PhS• 8. Please provide a mechanism for the illustrated transformation. I O Me 3 O 3 SnBu cat. AIBN, ∆ cat. HSnBu Me...
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