KAHR sample exam honors

KAHR sample exam honors - CHEM 337 SPRING 2006 PRACTICE...

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CHEM 337 SPRING 2006 PRACTICE EXAM 1 NAME__________________________________________________________ 1. (T18.18) {14 pts} Propose a structural formula for each compound consistent with its 1 H-NMR and 13 C- NMR spectra. (a) C 7 H 14 O 2 ( b ) C 4 H 6 O 2 1 H-NMR 13 C-NMR 1 H-NMR 13 C-NMR 0.92 (d, 6H) 171.15 2.29 (m, 2H) 177.81 1.52 (m, 2H) 63.12 2.50 (t, 2H) 68.58 1.70 (m, 1H) 37.31 4.36 (t, 2H) 27.79 2.09 (s, 3H) 25.05 22.17 4.10 (t, 2H) 22.45 21.06 CH 3 C(O)OCH 2 CH 2 CH(CH 3 ) 2 2.09 4.10 1.52 1.70 0.92 C H 2 C H 2 CC H 2 O O 2.50 2.29 4.36
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2. (T 18.27) {15 pts} Show the product of the treatment of this anhydride with each reagent(s). O H H O O H 2 O, HCl H 2 O, NaOH, 1. LiAlH4 2. H 2 O CH 3 OH NH 3 (2mol) COOH COOH H H COO - Na + COO - Na + H H CH 2 OH CH 2 OH H H COOH COOCH 3 H H COO - NH 4 + CONH 2 H H
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Propose a mechanism for the formation of this bromolactone and account for the observed stereochemistry of each substituent on the cyclohexane ring. CH
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KAHR sample exam honors - CHEM 337 SPRING 2006 PRACTICE...

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