### Carbonyl Reagent Selection

In each reaction box enter a letter designating the best reagent and conditions selected from the list at the bottom of the page.

Reactant | Reagent | Product | Answer Evaluation |  | Response Box
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(CH3)2CHCOCH3 3-methyl-2-butanone |  | (CH3)2CHCH(OH)CH3 3-methyl-2-butanol |
| (CH3)2CHC(OC2H5)2CH3 2,2-diethoxy-3-methylbutane
| (CH3)2CHCOH(C6H5)CH3 3-methyl-2-phenyl-2-butanol
| (CH3)2CHCH2CH3 2-methylbutane

(CH3)2CHCH2CHO 3-methylbutanal |  | (CH3)2CHCH2CH3 2-methylbutane |
| C6H5CH(OH)CH2CH(CH3)2 3-methyl-1-phenyl-1-butanol
| (CH3)2CHCH2CH2OH 3-methyl-1-butanol
| (CH3)2CHCH2CO2H 3-methylbutanoic acid
| (CH3)2CHCH2CH(OC2H5)2 1,1-diethoxy-3-methylbutane

CH3CH2COCH2CH3 3-pentanone |  | C6H5C(OH)(C2H5)2 3-phenyl-3-pentanol |
| (C2H5)2C(OC2H5)2 3,3-diethoxypentane
| CH3(CH2)3CH3 pentane
| C2H5CH(OH)C2H5 3-pentanol

REAGENTS
A. Jones' reagent CrO3 in H3O(+) | B. C6H5MgBr in ether, followed by H3O(+) | C. excess C2H5OH acid catalyst, heat (–H2O) | D. (CH2)5NH (piperidine) acid catalyst, heat (–H2O) | E. N2H4, KOH heat (–H2O) | F. NaBH4 in CH3OH
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This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.