su08org1e3

su08org1e3 - a =18 pK a =10...

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Name June 17, 2008 Exam3 Summer 2008 Chapters 9-11 100points 1) Give the products (if any) formed in the following reactions: (10pts) H H 3 C CH 3 H excess H 2 , Pt H 3 C C C H excess H 2 , Pt CH 3 CH 2 CH 2 CH 3 excess H 2 , Pt H 3 C C C CH 3 H 2 Lindlar's catalyst H 3 C C C CH 3 Na, NH 3 2) Name (in IUPAC form) the following three compounds. (12pts) OH OH Cl HO Cl Left: Middle: Right: 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc - 1 -
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3) Indicate for each reaction if the process is an oxidation , reduction or neither . (8pts) a) CH 3 CH 3 b) c) CH 3 CH 3 d) OH OH O O OH OH 2) Fill in the question marks with reagents and products. (12pts) OH ? Br Mg, ether ? OH PCC ? H 3 O + ? CrO 3 , H 2 SO 4 O 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc - 2 -
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5) Explain the formation of all products in this elimination reaction by drawing mechanisms. Put the symbol for the mechanism over the arrow. (15pts) OH + + 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc - 3 -
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7) Alcohols are weak acids, circle the weaker acid of each pair: (4pts) OH H 3 C OH CF 3 CF 2 CF 2 OH CH 3 CH 2 CH 2 OH a) b) Explain why phenol is 10 8 times more acidic than cyclohexanol. (7 pts) OH OH pK
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Unformatted text preview: a =18 pK a =10 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc- 4 -8) Give reagents for the following transformations (respecting order of use). (18pts) OH Br OH H OH SH OH O OH O H CH 3 a) b) c) d) e) OH OH f) 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc- 5 -9) Draw the products of the following transformations. (10pts) O O R O O O R O 1. LiAlH 4 2. H 3 O + 1. NaBH 4 2. H 3 O + H 3 C H 1. NaNH 2 2. CH 3 Br OH SOCl 2 HO OH HIO 4 a) b) c) d) e) 10) Write the symbols for the mechanisms over the reaction arrows. (4pts) 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc- 6 -R OH Br P Br Br R O H P Br Br + Br-Br R BONUS (2 pts for each correct transformation) Fill in the arrows that explain how each molecule rearranges. CH N HC MeN CH N O O Y CN X N CH MeN NH O O Y CN X N C H N Me C C CH HC Y O O X HC N CH MeN NH O O Y CN X N N 75a59b008f8011a5daad3a5a0679aedbcd052ee0.doc- 7 -...
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su08org1e3 - a =18 pK a =10...

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