W03 problems1b key

W03 problems1b key - 3 NaNH 2 deprotonates the alcohol...

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H 2 SO 4 H 2 O OH Problem Set 1 (Chepter 9 Alcohols and Thiols) TA: Danny Ng 1/13/2002 A . S y n t h e s i s o f A l c o h o l s f r o m A l k e n e s ( R e v i e w ) 1. Provide the missing reagents or products for the following reactions. Include all possible stereoisomers whenever applicable 1. Hg(OAc) 2 , H 2 O 2. NaBH 4 B . N o m e n c l a t u r e s o f A l c o h o l 2. (i) Provide the structure for the following compounds and (ii) Identify whether the alcohols are primary, secondary, or tertiary. (a) 5-bromo-1,2,6-trimethylcycloheptanol (b) cis -1,2,4-cyclooctanetriol OH OH 1. BH3 2. H 2 O 2 , NaOH OH OH Br tertiary OH OH OH secondary Answer Key
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H H HO OH OH HCl SOCl 2 , pyridine H 3 C S O O Cl OH HO OH OH PCC H 2 CrO 4 Br Br O H H Cl H H Cl I O O H O O OH H H Cl Problem Set 1 (Chepter 9 Alcohols and Thiols) TA: Danny Ng 1/13/2002 C . R e a c t i o n s o f A l c o h o l s 3. Provide the missing reagents or products for the following reactions. Include all possible regioisomers and/or stereoisomers whenever applicable (Indicate the major isomers). 1. NaNH 2 2. 1-bromopropane 1. pyridine 2. NaI excess PBr
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Unformatted text preview: 3 NaNH 2 deprotonates the alcohol, forming alkoxide, which becomes a good nucleophile SOCl 2 proceeds via SN2 mechanism, inversion of configuration; with HCl, carbocation intermediate possible, hence mixture of isomers Answer Key F OH OH PCC F OH OH OH OH HIO 4 OH 2 Br H F Br H OH HO OH 2 O O OH 2 F Br X H 2 SO 4 Br Br SN2 O Br Br O Problem Set 1 (Chepter 9 Alcohols and Thiols) TA: Danny Ng 1/13/2002 H 2 SO 4 , heat 4. Predict the major products for the following reactions and explain the difference in reactivity. H 2 SO 4 , heat 5. Explain the following reaction with a mechanism. major No reaction Too hindered for SN2 - beta branching Instead. .. methyl migration Answer key OH HO H-OSO 3 H OH 2 HO HO-H + O OH HO H-OSO 3 H OH H 2 O OH-H + O...
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This note was uploaded on 04/05/2008 for the course CHEM 30B taught by Professor Rubin during the Winter '05 term at UCLA.

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W03 problems1b key - 3 NaNH 2 deprotonates the alcohol...

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