Chem 317 - Set 4 extra problem Solutions

Chem 317 - Set 4 extra problem Solutions - a) O O b) O O c)...

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CHEM 317 PS 4 Aldehydes and Ketones: Solutions 1. Rank the following carbonyl compounds in order of increasing equilibrium constant for hydration. 2. Complete the following reactions: O O O A B C D 3.In the reaction of ethyl acetoacetate with an excess of 1,3-propanediol and acid catalysis (as shown below), one acetal product predominates. How do the electronics of the starting material allow for selectivity in this reaction? Draw the mechanism for the formation of the product. O O O HO OH H + -H 2 O O O O O O Cl Cl H O H H O O H O A =HO OH , H + B = 1) NH 2 NH 2 2) hot KOH C = 1) 2) heat and H + MgBr D = Ph 3 PCHCH 2 CH 2 CH 2 CH 3 O O O H + O O OH O HO H O O OH O HO H + O O OH 2 O HO O O O HO O O OH O
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CHEM 317 PS 4 Aldehydes and Ketones: Solutions 4. Propose two fundamentally different syntheses for each of the following molecules: a. O OH from compounds of 6 C or fewer; any functional group present. One possibility would use the phenomenon in question 3 to aid in selectivity . b. O NH from compounds of 4 C or fewer; any functional group present. 5. Show what compound(s) result from complete hydrolysis of:
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Unformatted text preview: a) O O b) O O c) O O d) HO O 1) Br O HOCH 2 CH 2 OH H + Mg Ether O H 3 O + PCC HOCH 2 CH 2 OH H + 1) CH 3 MgBr 2) H 3 O + 2) OH CH 3 OH O OH HO O O HO OH O OH + mCPBA MgBr 1 2) H+ 1) BH 3-THF 2) NaOH/H 2 O 2 PCC 1) + O O CH 3 NH 2 2) + O O CH 3 NH 2 H 2 /Pd CHEM 317 PS 4 Aldehydes and Ketones: Solutions 6. Show how you would accomplish the following syntheses efficiently and in good yield using any necessary reagents. a) CH 3 CH(OH)COOH from acetaldehyde b) O OH from O O H c) O O H from OH OH d) OH O H from O O H e) O from O 7. Draw structures of the following: a) 8. Predict the product(s) formed when cyclohexanone reacts with the following reagents: O Ph 3 PCH 2 1) mCPBA 2) H 3 O + KMnO 4 1) LAH 2) H + HOCH 2 CH 2 OH H + NaBH 4 H 3 O + HOCH 2 CH 2 OH H + H 2 /Pt H 3 O + N HN O 2 N NO 2 b) O O c) N d) H HO OMe H a) N b) c) O O d) OH e) O O f) no reaction 9. O O and fit without J values...
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This homework help was uploaded on 04/09/2008 for the course CHEM 317 taught by Professor Kantorowski during the Fall '08 term at Cal Poly.

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Chem 317 - Set 4 extra problem Solutions - a) O O b) O O c)...

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