Chem 317 - Set 4 extra problems

Chem 317 - Set 4 extra problems - 6. Show how you would...

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CHEM 317 PS 4 Aldehydes and Ketones 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 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. O Cl Cl H O H H O O H O 5. Show what compound(s) result from complete hydrolysis of: a) O O b) O O c) O O d) HO O
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CHEM 317 PS 4 Aldehydes and Ketones
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Unformatted text preview: 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) the 2,4-dinitrophenylhydrazone derivative of benzaldehyde b) acetaldehyde dimethyl acetal c) the (E) isomer of the ethyl imine of propiophenone d) the methyl hemiacetal of formaldehyde 8. Predict the product(s) formed when cyclohexanone reacts with the following reagents: a) methylamine, H + b) hydrazine, then hot KOH c) ethylene glycol and p-toluenesulfonic acid d) sodium acetylide, then mild acid e) excess methanol, H + f) Tollens reagent 9. A volatile liquid with molecular formula C 4 H 6 O has the following NMR and IR. Deduce the structure. 1 3 2...
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Chem 317 - Set 4 extra problems - 6. Show how you would...

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