w-03072009140052zVplBcUmyE

w-03072009140052zVplBcUmyE - 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 CH H 3 C N CH O H O OCH 3 H O 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 2 MgBr 1) 2) H 3 O + OH PBr 3 Br O OO O + + NaH O O NaOH (or NaH . ..) O O - Na + SOCl 2 or PCl 3 O Cl 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 O H H H O H H H e) Cl OH H 2 NCH 2 CH 3 3 O O O C 14 H 22 O 4 H 3 NCH 2 CH 3 Cl For a, part a heat and O O O 1) 2) H 3 O + (protonation) Or alkyl lithium
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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? H 3 C O CH 3 pK a 20 CH 2 O CH 3 N 3 The pKa of the hydrogens of the azido substituted CH 2 in Compound Z will be ( circle one ): lower OR higher than 20.
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w-03072009140052zVplBcUmyE - Name:_ Page 1(W.07.215.E2 p1)...

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