11-24 - How could the following transformation be...

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Unformatted text preview: 11/24/2010 How could the following transformation be accomplished? What is the product of reaction B? A no reaction A no reaction B B C C What is the product of reaction C? What is the reaction mechanism of reaction sequence C? A no reaction B C C What is the reaction mechanism of reaction sequence C? pKa data clearly show OH is a better leaving group than H2O H in substitution reactions. C O H C O H A. True B. False CH3 O H3C H H O O S O CH3 pKa C 1 11/24/2010 pKa data clearly show OH is a better leaving group than H2O H in substitution reactions. C O H C O H pKa data clearly show OH is a better leaving group than H2O H in substitution reactions. C O H C O H pKa pKa Alcohols can be converted to bromides using H-Br. H C O H +H Br C O H Do all alcohols react by a SN2 reaction mechanism? H H + Br C Br + O H C O H +H Br C O H + Br C Br H + O H What is the mechanism of this reaction? A. Yes B. No H Br + C O H H Br + C O H SN2 H Br C O H SN2 H Br C O H What other mechanism can occur in this reaction? H C O H +H Br C O H + Br C Br H Which mechanism will 2-methylpropan-2-ol be predicted to follow when it reacts with H-Br? H H Br C O H + O H Br H Br + C O H C O H H Br C C O H H Br C O H Br H SN2 (A) Br C + C Br SN2 + O C H SN1 (B) C CH3 H3C C CH3 H3C CH3 C Br CH3 SN1 C 3° CH3 H3C C OH CH3 H Br SN 1 2 11/24/2010 Which mechanism will butanol be predicted to follow when it reacts with H-Br? H Br H C O H C O H If the transition state is a carbocation or carbocation like which of the following alcohols would be predicted to react faster? SN2 CH3 H3C Br C + C Br C OH CH3 C O H H Br (A) (B) C H Br CH3 H3C C CH3 H3C CH3 C Br CH3 H2O SN1 A CH3 CH2 CH2 CH2 OH H Br CH3 CH2 CH2 Br C HH OH2 CH3 CH2 CH2 CH2 Br 3° CH3 H3C C OH CH3 H Br H Br CH3 H3C C CH3 H3C CH3 C Br CH3 CH3 CH2 CH2 CH2 Br B H2O SN 1 CH3 CH2 CH2 CH2 OH CH3 CH2 CH2 Br C HH OH2 1° SN 2 Order of alcohol reactivity with HBr: 1° < 2° < 3° increasing reactivity CH3 H 3C C OH CH3 H Use the curved arrow formalism to show the bond making and bond breaking in the following transformation. O Cl S Cl Br CH3 H3C C CH3 H3C CH3 C Br O H Cl O S Cl Cl CH3 H2O A CH3 CH2 CH2 CH2 OH H Br CH3 CH2 CH2 Br C HH OH2 CH3 CH2 CH2 CH2 Br R3N H2O B Choose a reasonable intermediate structure in the reaction mechanism. O Cl S Cl O O S Which of the following reactions would you predict to occur at a faster rate? Which sulfonate anion is the best leaving group? Cl A O O H Cl S Cl Cl O H H pKa of the conjugate acid O O S CH3 O N3 O N3 + O S CH3 O R3N B O Cl A -1.9 O Cl O O S H C S Cl O S CF3 O N3 O N3 + O S CF3 O B -15 Cl D O 3 11/24/2010 What reactant might be used to prepare sulfonate esters? How can these sulfonate esters be prepared from the alcohol? O O S CH3 O Cl O S Cl Cl O S CH3 Cl O S CH3 O O S CH3 O Cl O Cl S O Et3N CH3 O O H S O S O CH3 O CH3 ? O A H Cl O S Cl O B O HO S O CH3 O C O H D E Use the curved arrow formalism to show the bond making and bond breaking in the following transformation. In the first step benzyl alcohol is behaving as an acid. A. True B. False Ethers can be prepared by the treatment of alcohols with H+. Use the curved arrow formalism to show the bond making and bond breaking in this following transformation. HO O H H O -H2O H H -H O H H O O H H O Predict the product(s) of the following reaction. Predict the product(s) of the following reaction. H HO CH3 A. H 3C O CH3 H O + -H2O HO CH3 A. H 3C O CH3 B. O CH3 O H H B. O CH3 O H + HO CH3 C. H O H O H + HO CH3 C. H O D. All of the above. D. All of the above. 4 11/24/2010 Predict the product(s) of the following reaction. A. O H 3C O CH3 B. O CH3 O H C. 1. Na :H 2. CH3 Br O D. All of the above. 26 5 ...
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