mar_12 - 3/12/2010 O O O O O O O O H + HO Na OH OH O a...

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Unformatted text preview: 3/12/2010 O O O O O O O O H + HO Na OH OH O a solution NaCl! O Na a solid O How was solid soap obtained from the solution? A. A. The water was allowed to evaporate. B. The solution was cooled and the soap precipatated. C. An organic solvent was added to the solution. D. Salt was added to the solution. Predict the Keq of the following equilibrium. O H H C H C O H C H H + O H O H H H H C H C O H + H O H C H H Predict the Keq of the following equilibrium. O H H C H C O H C H H + N H O H H H H C H C N H H + H O H C H H O H H C H C O H C H H O H H C H C N H H A about 1.0 B much greater than 1.0 C much less than 1.0 Consider the C=O resonance energies. A about 1.0 B much greater than 1.0 C much less than 1.0 What is the mechanism of this reaction? O + H H C H C N H H + What is the mechanism of this reaction? + + O H3C H C N H O H H C H H O H2C H C N H O H H C H H E R 1 3/12/2010 Which of the following reactions would be predicted to occur at a faster rate? O C O CH3 + H N CH3 Which of the following reactions would be predicted to occur O Cl at a faster rate? O OCH 3 A O C N CH3 O C O CH3 Nu Nu CH3 CH3 O C O O CH3 Cl O Cl H + N CH3 B O C N CH3 O Cl E O OCH3 O Nu CH3 CH3 O C Cl R Choose the answer that has the following C=O groups arranged correctly with respect to increasing reactivity towards nucleophiles. O R i N R R R O O ii O R R iii O O R Summary. Order of C=O reactivity. O R Cl R O O O R R O O R R O N R R increasing reactivity stability of C=O O R N R R R O O O R R O O R leaving group ability A i < ii < iii D i i < ii i < i B i < i ii < i i E iii < ii < i C i i < i < iii F iii < i < ii Summary. Order of C=O reactivity. O R Cl R O O O R R O O R R O N R O X R C X Nu R Consider the following reaction. Which of the following reaction path would be predicted to be more reasonable? N O O O CH3 CH3 CH3OH increasing reactivity O R C Nu X R O C Nu A B N O O CH3 OCH3 O N OCH3 O CH3 energy progress of reaction 2 3/12/2010 Predict the product of the following reaction. Which of the following reactions would be expected to occur as shown? O N O O O CH3 CH3 O CH3OH HN OCH3 O CH3 1 O Cl + O Ph C O Cl Ph O C O + Cl Ph C 2 O N OCH3 O CH3 O OCH3 N O CH3 O Ph C NH2 + Cl O Ph C Cl Ph O C + Cl NH2 NH2 3 Ph O C Cl + O O C O Ph O C O O C + Cl N O CH2 O N HO CH3 O N O H O HN OCH3 CH3 O Ph C O Cl A B C D A1 B2 C3 D 1+2 O E 2+3 F 1+3 Draw the mechanism for the hydrolysis of a nitrile to an amide. O R C N H H2O R N H H Give a good mechanism for the acid catalyzed hydrolysis of a nitrile to the amide. O R C N H H2O H H2O R N H -H H Which of the following is not an intermediate in the not mechanism? H R C N H O C H H H O C N H H O R C N H H H H O C N H H R C N H H O C H H H O C N H H O R C N H H H H O C N H H R N R R R N R R A B C D E Continued exposure of the amide to aqueous acid results in hydrolysis to the carboxylic acid. O R C N H H2O R N H H H H2O R O O H Give the reaction mechanism for hydrolysis of the amide in aqueous acid to the carboxylic acid. O R C N H H2O R N H H H H2O R O O H Nitriles are reactants for the synthesis of both amides and carboxylic acids. ? 3 3/12/2010 Choose the structure least likely as an intermediate in the acid catalyzed hydrolysis of the amide to the carboxylic acid. O R C N H H2O R N H H H H2O R O O H Continued exposure of the amide to aqueous acid results in hydrolysis to the carboxylic acid. O R C N R N H H -H H H H2O R O O H ? O R C H N H H H 2O O R H C O H H N H H H H N H H R R O C O H H N H H H H R H R O C H H O O R C O H H N H H H H R O C O N H R H H H O C O H H N H H R O C H H R O C H H R O C O H H N H H H H R O C O N H R H H H O C O O C O C H H O N H O N H A B C D E 4 ...
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This note was uploaded on 04/06/2010 for the course CHE 326 taught by Professor Fowler during the Spring '08 term at SUNY Stony Brook.

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