310NHWSet1ans - Homework Problem Set 1 Iverson CH310N Due...

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Unformatted text preview: Homework Problem Set 1 Iverson CH310N Due Wednesday, January 25 3 O H 2 SO 4 O H H H 2 O H C l Cl Cl Cl 2 HBr HBr ROOR OH H Br CH 3 CH 3 Br H OH Br 2 H 2 O 1) OsO4 CH 3 H OH OH OH OH H CH 3 1 ) B H 3 2 ) H 2 O 2 / H O racemic h 1) O 3 2) (CH 3 ) 2 S 2) NaHSO 3 / H 2 O (3 or 5 pts each) Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. If a racemic mixture is produced, you must draw both enantiomers and write the word "racemic". If more than one carbon containing product is produced, you must draw all of them. racemic racemic Cl Cl OH not chiral Cl not chiral Br not chiral H Br racemic Br H H OH racemic OH H Homework Problem Set 1 Iverson CH310N Due Wednesday, January 25 4 h NBS Br Br Racemic HBr HBr ROOR (Assume NO rearrangement) HBr (Assume rearrangement) Br h Br Br Br 2 Br Br Br Br Racemic O E2 S N 2 Na OCH 2 CH 3 Na OCH 2 CH 3 (3 or 5 pts each) Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. If a racemic mixture is produced, you must draw both enantiomers and write the word "racemic". If more than one carbon containing product is produced, you must draw all of them. Homework Problem Set 1 Iverson CH310N Due Wednesday, January 25 5 + (5 or 7 pts each) The following reactions all involve substitution and/or elimination. Fill in the box above the arrow with the mechanism that will be followed (S N 2, E2, etc.) . Then draw only the predominant product or products and please remember that you must draw the correct stereoisomers . When a scrambled mixture is formed, you must write "scrambled" under both structures EVEN THOUGH YOU DREW BOTH STRUCTURES . For S N 1/E1 reactions you must draw both types of products. + C. A. E. B. D. S N 2 S N 2 S N 1/E1 E2 + CH 3 OH Inversion Zaitsev product Na N 3 CH 3 CH 2 O Na Na SH I SH Br CH 3 H N 3 CH 3 H Br H Na CN + H 3 C H S N 2 H CN H 3 C H Inversion Br H H 3 C H CH 3 Br CH 3 OCH 3 CH 3 Not Chiral CH 3 Zaitsev heat Homework Problem Set 2 Iverson CH310N Due Wednesday, February 1 3 Li O MgBr O CH 3 CH 2 OH C H 3 C H 2 O H O MgBr HCl H 2 O OH Li 2 Li MgBr Br O (3 or 5 pts each) Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. If a racemic mixture is formed, you must draw both enantiomers and write "racemic" next to the two structures. + Mg ether New C-C bond made!! + LiBr Homework Problem Set 2 Iverson CH310N Due Wednesday, February 1 4 CuI Li Br CuLi O O OH O MgBr CuLi Li OH OH Cu LiBr (3 or 5 pts each) Fill in the boxes with the structures that complete the reactions. Use wedges and dashes to indicate stereochemistry when appropriate. If a racemic mixture is formed, you must draw both enantiomers and write "racemic" next to the two structures....
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This note was uploaded on 02/27/2012 for the course CH 310n taught by Professor Iverson during the Spring '08 term at University of Texas at Austin.

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310NHWSet1ans - Homework Problem Set 1 Iverson CH310N Due...

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