ps7_optional - Relative Rate O KOAc, AcOH OAc 7 x 10 7 OSO...

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Massachusetts Institute of Technology 5.13: Organic Chemistry II Fall 2003, S. Tabacco Optional Problem Set 7 If you would like feedback from your TA, please turn your problem set in by 4PM on Tuesday, December 2nd. 1. With the aid of three-dimensional drawings, provide a clear rationale for the products that are observed in the following transformations. Your rationale must include the mechanism for each transformation. Hint: Think cyclohexane chair! OH H O H H H 2 O, OTs OTs H OH O H 2 O, 2. Please provide a detailed mechanism for the illustrated transformation. HO OMe F 3 C OH O OMe 3. Please provide a detailed mechanism that accounts for the formation of all three of the observed products. Hint: Think Beckmann rearrangement. O O H N Me O O O Me 1. NH 2 OH, HCl O N N O H Me 2. PCl 5 , O O O O Me
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4. a) Please provide a rationale for the illustrated rate data.
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Unformatted text preview: Relative Rate O KOAc, AcOH OAc 7 x 10 7 OSO 2 Ar O H H KOAc, AcOH 1 H OAc O O OSO 2 Ar H b) Please provide a mechanism to account for the formation of the products illustrated below. In addition, explain why no other stereoisomers are generated in the reaction. KOAc, AcOH OSO 2 Ar OAc AcO O O O D D D H 5. Please provide a detailed mechanism for the illustrated transformation. NH 2 HO HO HO HO NH Me H + MeCHO 6. In the reaction illustrated below, the desired product from a simple FriedelCrafts acylation ( A ) was not observed. Instead, and isomeric product ( B ) was generated through a more complex route that also involves FriedelCrafts chemistry. Please provide a detailed mechanism for this unexpected process. CO 2 H OMe O OMe Me OMe O OMe Me OMe O O O Me HF OMe OMe OMe OMe A B desired not desired not observed observed...
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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ps7_optional - Relative Rate O KOAc, AcOH OAc 7 x 10 7 OSO...

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