Problem_Set_7___solutions - concise reasons for your...

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Chem 3580 - Spring 2009 Problem Set 7 - Solutions 1. In (a) provide the major organic product of each transformation. In (b) provide the reagents you would use to obtain the indicated products in good yield. H O 1. LiAlH 4 2. H 2 O HO OH Zn[Hg], HCl 1. NaBH 4 2. H 2 O H 2 Pt KOH, ! H NNHPh H OH H OH H NPh H O O H OH PhNHNH 2 HCl PhNH 2 H 2 NNH 2 O Ph OH OH Ph OH N 1. CH 3 MgBr 2. H 2 SO 4 , ! 1. CH 3 MgBr 2. H 3 O + 1. PhMgBr 2. H 3 O + N H Ph 3 P 1. LiAlH 4 2. H 3 O + 1. NaBH 4 2. H 2 SO 4 , ! 1. PhMgBr 2. H 2 SO 4, ! HCl
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2. Give the major organic product of each of the reactions shown below O O + SH EtONa (catalyst) EtOH (solvent) O 1. (CH 3 ) 2 CuLi, ether, -78°C 2. H 2 O O 1. (CH 3 CH 2 CH 2 ) 2 CuLi, ether, -78°C 2. H 2 O 3. Zn[Hg], HCl O Li 1. 2. H 3 O + 1. NaCN 2. HCl, H 2 O, ! Ph O N H CN (a) (b) (c) (d) (e) (f) O O S O O Ph OH + HO OH O O Ph O N major minor Steric congestion is about the same at both sites. Ketone is relatively unreactive (compared to an aldehyde). 3. (a) Each of the following compounds contain acidic CH 2 groups. From the list below select the compound whose CH 2 having (i) the lowest pKa and (ii) one having the highest pKa. Provide clear but
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Unformatted text preview: concise reasons for your choices . (a) (i) Lowest pKa B (ii) Highest pKa C Aldehydes have the most pK a-lowering effect than ketones that in turn are more effective than esters. On your own, draw the appropriate resonance structures to support this assertion. (b) Circle only the most acidic H in each of the following compounds and select the compound that will give (i) the highest amount of the enol isomer and (ii) one that will give the lowest amount of the enol. Give reasons. O H H H H O O H H H H H H O O H H H O O H H H A B C B will give the highest enol concentration because it is the strongest acid (keto-aldehyde) while A will give the lowest because it is the weakest acid (keto-ester). Note that C is a diketone. So it will be in-between....
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This note was uploaded on 09/07/2009 for the course CHEM 2183 taught by Professor Jonnjardarson during the Spring '09 term at Cornell University (Engineering School).

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Problem_Set_7___solutions - concise reasons for your...

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