118bpracticefinal

118bpracticefinal - a) b) c) d) OH O H H H H O H O O CH 3 8...

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1 Name____________________ TA____________________ CH118b Practice Final Exam Closed Book and Notes Points: 1.______ 2.______ 3.______ 4.______ 5.______ 6.______ 7. ______ 8.______ Total ______
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2 Problem 1 Propose a curved arrow mechanism for the following reaction: CH 2 OH H 2 SO 4 H 2 O CH 2 + CH 3 +
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3 Problem 2 Propose a curved arrow mechanism for the following reaction: O CH 3 CH 3 O + KOH EtOH O
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4 Problem 3 Propose a curved arrow mechanism for the following reaction: O + 2 CH 3 OH SO 3 H OCH 3 OCH 3 + H 2 O
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5 Problem 4 Provide the necessary reagents to carry out the following synthetic transformations: (Note: More than one step is necessary for each synthesis!) a) b) c) ? OCH 3 OH OH ? O O HO OH H H ? H 3 C H
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6 Problem 5 Predict the major products for each of the following reactions, showing stereochemical relationships where appropriate: a) O OCH 3 LiAlH 4 ether H 3 O + b) c) d) O H 3 C H H 3 C CH 3 H 2 SO 4 CH 3 OH H H CH 3 NBS, H 2 O DMSO O O O O + 150 °C
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7 e) mCPBA CHCl 3 Problem 6 Provide the reagents necessary to carryout the following transformations:
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Unformatted text preview: a) b) c) d) OH O H H H H O H O O CH 3 8 e) Problem 7 Suggest structures that are consistent with the molecular formula and spectroscopic properties of each of the following: Formula 13 C NMR ( 1 H decoupled) 1 H NMR Chemical shift Integral ratio C 5 H 10 O 2 180, 30, 14 1.3 singlet 9 11.3 singlet 1 Formula 13 C NMR ( 1 H decoupled) 1 H NMR Chemical shift Integral ratio C 8 H 14 O 4 170, 52, 20, 16 1.3 triplet 6 2.6 singlet 4 4.2 quartet 4 O OCH 3 O OCH 3 O 9 Problem 8 Illustrate the meaning of the following terms by drawing a structure, diagram, reaction or providing a short definition. a) a hemiacetal b) thermodynamic control c) dienophile d) Michael reaction e) transition f) Saytzev's rule...
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This note was uploaded on 05/14/2011 for the course PSC 113 taught by Professor Staff during the Spring '08 term at UC Davis.

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118bpracticefinal - a) b) c) d) OH O H H H H O H O O CH 3 8...

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