4.10 quiz key

4.10 quiz key - Br Br HO OH HO 1. NaNH 2 , CH 3 Br 2. NaNH...

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SYNTHESIS PRACTICE 1. Some simple reactions to enlarge the carbon chain. You may use carbon reagents of 5C or less. ? (1 step) NaNH 2 and 1-bromo-2-methylpropane ? (1 step) NaNH 2 and 1-bromo-2-methylbutane 2. Once you have the appropriate number of carbons in the chain, you should be able to chan ge the functional group! Br ? (2 steps) NaNH 2 and ethylbromide followed by HBr addition H 3 CO ? (3 steps) NaNH 2 and 1-bromo-2-methylpropane followed by H 2 /Lindlars followed by CH 3 OH/H+. 3. Try to convert ethyne (acetylene) to all the given molecules with the appropriate number of steps.
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O H ? ? (3 steps) ( 2 steps) (3 steps) Br (3 steps) Cl Cl (5 steps) ONLY 4 STEPS 1. NaNH 2 , 1-bromo-2- methylpropane 2. H 2 /Pt 3. Br 2 /heat 4. KOH, heat 1. NaNH 2 , CH 3 Br 2. NaNH 2 , CH 3 Br 3. Li, NH 2 , low temp 1. NaNH 2 , ethylbromide 2. DSB followed by oxidation 1. NaNH 2 , CH 3 Br 2. NaNH 2 , CH 3 CH 2 Br 3. Cl 2 , CCl 4 1. NaNH 2 , 1-bromo-2-methylpropane 2. H 2 , Pt 3. Br 2 , heat 4. Now try adding stereochemistry!
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? ? (3 steps) ( 4 steps) (4 steps)
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Unformatted text preview: Br Br HO OH HO 1. NaNH 2 , CH 3 Br 2. NaNH 2 , CH 3 Br 3. H 2 /Lindlars ( 4. Br 2 , CCl 4 1. NaNH 2 , CH 3 Br 2. H 2 /Lindlars or Li/NH 3 3. H 2 O/H+ or mercuric-cataylzed hydration 1. NaNH 2 , CH 3 Br 2. NaNH 2 , CH 3 CH 2 Br 3. H 2 /Lindlars (NOT Li/NH 3 ) 4. OsO 4 /NaHSO 3 NOT Li/NH 3 ) 5. And finally some harder problems (without the number of steps given!). a. Conversion of cyclohexane to 1,3-cyclohexandiene 1. Br 2 /light; 2. KOH, heat; 3. Br 2 (NBS), light; 4. KOH, heat b. Conversion of cyclohexane to (RR)-1,2-dibromocyclohexane. 1. Br 2 ,light; 2. KOH; 3. Br 2 , CCl4 c. Hexane to 3-octanone. 1. Br 2 , light; 2. KOH; 3. Br 2 /CCl4; 4. KOH 5. NaNH 2 , CH 3 CH 2 Br; hydroboration or mercuric-catalyzed hydration d. 2-methylbutane to 3-methyl-3-butanol 1. Br 2 , light; 2. KOH; 3. H 2 O, H+ or mercuric-catalyzed hydration...
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This homework help was uploaded on 04/20/2008 for the course CHEM 231 taught by Professor Montaguesmith during the Spring '06 term at Maryland.

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4.10 quiz key - Br Br HO OH HO 1. NaNH 2 , CH 3 Br 2. NaNH...

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