11-29 - 11/29/2010 How could the following ether be...

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Unformatted text preview: 11/29/2010 How could the following ether be prepared? i How could the following ether be prepared? i ii ii iii iii A=i B = ii C = iii D = i + ii E = ii + iii F = i + iii H O H What is(are) the major product(s) of the following reaction? A B C D E F A+B all of the above What is(are) the major product(s) of the following reaction? What is(are) the major product(s) of the following reaction? Propose a synthesis of methyl t-butyl ether (MTBE) from compounds containing four carbon atoms or less. O H CH3 H3C O CH3 C CH3 CH3 ? ? 1 11/29/2010 Propose a synthesis of methyl t-butyl ether (MTBE) from compounds containing four carbon atoms or less. Epoxides are very reactive ethers. Propose a synthesis of styrene oxide from styrene. C Nu SN2 Nu= N3, OR, CN, etc. C Br A=i B = ii C = i and ii CH3 H3C O C CH3 CH3 E none of these ? ? Williamson ether synthesis C O CH3 O R OR C Br CH3 H3C O C CH3 CH3 CH3 Br CH3 O CH3 C CH3 CH3 CH3 Na H HO C CH3 i styrene oxide styrene H3C C H3C CH2 Br C CH3 CH3 Na H O CH3 HO CH3 ii Choose reactants and reagents that could be used to prepare styrene oxide. A. i D. iv B. ii E. i+iv C. iii Na :H OH How could a bromohydrin be prepared from styrene? F. ii + iii i OR Br Williamson ether synthesis C O Br OH Na :H O Br O R OR C Br ii OR iii iii styrene oxide styrene Na :H ? Br Na :H Br styrene oxide OH iv OH Choose the correct reaction sequence for the preparation of styrene oxide from styrene. Are there any other syntheses of epoxides? R O O H O A. Na :H O OH Br RCO3H Br O Br Br O H H Na :H OH Br Br H O H Br styrene oxide Na :H Br OH B. 2 11/29/2010 Using the curved arrow formalism show the bond making that transform the following intermediate into styrene oxide and the carboxylic acid. R O O H O Using the curved arrow formalism show the bond making that transform the following intermediate into styrene oxide and the carboxylic acid. R O O H O ? O RCO3H Na :H Br OH RCO3H O Na :H Br OH Using the curved arrow formalism show the bond making that transform the following intermediate into styrene oxide and the carboxylic acid. R O O H R O O RCO3H Na :H Br O H O Predict the major product of the following reaction. R O O H H CH3 + O H H H3C O R O H O H H O + CH3 H H O H OH CH3 RCO3H CH3 i A. i + ii B. ii + iii ii C. iii + iv iii D. i + iv iv E. ii + iv F. all How could a single enantiomer be prepared as the R R major product? O H O O H H CH3 + O H H H3C O O H One strategy would be to use a chiral reactant. R(S) O H O O H H CH3 + O H H H3C O R(S) O H (S(S-face) (R-face) (R- These two diasteriomeric transition states have different energies. O + CH3 H H CH3 O H O + CH3 H H O H H H CH3 RCO3H CH3 CH3 RCO3H i A. i + ii B. ii + iii ii C. iii + iv iii D. i + iv iv E. ii + iv F. all A. i + ii i B. ii + iii ii C. iii + iv iii D. i + iv iv E. ii + iv F. all 3 11/29/2010 Predict the major product of the following reaction. Predict the major product of the following reaction. OH Br H OCH3 H H OCH3 OCH 3 OCH3 OH O H / HO CH3 O O H / H2O O H H 2O OH Br OH OH OH OH O H OH OH OH O OH OH OCH3 OCH3 OH OCH 3 OH OCH3 A B C D E A B C D Predict the major product of the following reaction. O H O CH3 O CH3 O H Br O O O H CH3 CH3 O CH3 CH3 O O CH3 Br O O H CH3 O H OH OH OCH3 OCH3 OH OCH 3 OH OCH3 A B C D 22 4 ...
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