w-03072009140037E1jjHpUmIU

w-03072009140037E1jjHpUmIU - Name:_ Page 1(W.07.215.E2 p1)...

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Name:_____________________ Page 1(W.07.215.E2 p1) O OH O O b) J. Chem. Educ. 2006 , 83 , 1826 CH H 3 C N CH 2 O H O OCH 3 O OCH 3 H NaOCH 3 /HOCH 3 c) J. Chem. Educ . 2006 , 83 , 1826 O Cl 2 HO OH N(CH 2 CH 3 ) 3 + C 13 H 15 NO 4 CH 2 Br O OCH 2 HO CH 2 Br HO CH 2 Br K 2 CO 3 d) JOC 2006 , 71 , 9622 O O H OH PBr 3 O OO O + + NaH 2 22 2 3 3 3 3 3 I ( 26 points ) Complete the following reaction sequences, including stereochemistry as required. Label any multistep sets of reagents. You may use the abbreviation for lithium diisopropyl amide (LDA) if needed. a) OH H H H e) Cl OH H 2 NCH 2 CH 3 3 C 14 H 22 O 4 H 3 NCH 2 CH 3 Cl 1) 2) H 3 O + (protonation) +
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Name:_____________________ Page 2(W.07.215.E2 p2) II ( 18 points ) a) The substitution of an azido group (N 3 ) on acetic acid lowers its pK a from 4.76 to 3.03. NNN azido group H 3 C O OH CH 2 O OH pK a = 4.76 pK a = 3.03 Briefly explain (using one sentence) why the lowering of the pK a is observed. 3 b) Acetone may also be substituted with an azido group to form Compound Z. How will this affect the pKa of the hydrogens on the carbon where the azido group was substituted?
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This note was uploaded on 04/05/2009 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.

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w-03072009140037E1jjHpUmIU - Name:_ Page 1(W.07.215.E2 p1)...

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