Columbia CHEM C3046 - Problem Set (3 pages)

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Problem Set



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Problem Set

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Pages:
3
School:
Columbia University
Course:
Chem C3046 - Intensive Organic Chemistry for Freshmen
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Intensive Organic Chemistry for Freshmen Due March 23 2001 Problem Set 6 1 Draw products of the following reactions H a KCN H2SO4 O slight excess of KCN H H b SH HS HgCl2 B A O H CH3 CN H2O ZnCl2 c H N Li THF O H 2 Explain the following observations a HO OH O H2 O O b HO OH Ph F2 HC O O OH c HO HO d OH OH O OH O Ph F2 HC H2 O OH H HO OH OH O HO OH H 2O 3 Attempt to explain the following facts These are not simple questions and you may not find the answers in any textbook Think O H3CO OH H3CO OCH3 vs CH 3OH stable unstable H3CO Cl Cl OH O vs stable HCl unstable 4 Draw the product of this transformation and explain H2O H2SO4 Br 1 H 2O addition IR v 1710 cm 1 strong band 5 Draw the products of the following reactions a O OH A TsOH b CH3OCH2Cl methoxy methyl chloride MOM Cl is also used as an alcohol protecting group Explain in detail the mechanisms of both reactions protection deprotection CH3 OCH2Cl HCl aq B C THF Et3 N Base CH2 Cl2 HO deprotection protection 1 BH3 THF c O O 2 H2 O2 NaOH 3 H3 O D OH d solvent OH O H E TsOH heat Think twice 6 Complete the following synthetic sequence Br Mg metal O OH 1 CO2 A B Et2 O TsOH C 2 H3 O H deprotection D 7 Synthesize hydroxy ketone 1 from 2 Racemic product is OK but extra credit for optically pure product O O OH OH 2 1 8 Prepare R enantiomer of 4 from a racemic mixture OH OH Br Br R 3 4 9 Propose an enantioselective synthesis of intermediate 5 from the given starting material MeO O O Br


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