Skip to main content

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
(CH3)2CHCOCH3
3-methyl-2-butanone
reaction arrow
(CH3)2CHCH(OH)CH3
3-methyl-2-butanol


reaction arrow
(CH3)2CHC(OC2H5)2CH3
2,2-diethoxy-3-methylbutane

reaction arrow
(CH3)2CHCOH(C6H5)CH3
3-methyl-2-phenyl-2-butanol

reaction arrow
(CH3)2CHCH2CH3
2-methylbutane

reaction arrow		 Structure of the piperidine enamine of 3-methyl-2-butanone, an N-substituted vinyl amine
(CH3)2CHCH2CHO
3-methylbutanal
reaction arrow
(CH3)2CHCH2CH3
2-methylbutane


reaction arrow
C6H5CH(OH)CH2CH(CH3)2
3-methyl-1-phenyl-1-butanol

reaction arrow
(CH3)2CHCH2CH2OH
3-methyl-1-butanol

reaction arrow
(CH3)2CHCH2CO2H
3-methylbutanoic acid

reaction arrow		 Mechanism of enamine formation: ketone plus amine gives carbinolamine, then iminium ion, then stereoisomeric enamines

reaction arrow
(CH3)2CHCH2CH(OC2H5)2
1,1-diethoxy-3-methylbutane
CH3CH2COCH2CH3
3-pentanone
reaction arrow
C6H5C(OH)(C2H5)2
3-phenyl-3-pentanol


reaction arrow
(C2H5)2C(OC2H5)2
3,3-diethoxypentane

reaction arrow		 Structure of the piperidine enamine of 3-pentanone, an N-substituted vinyl amine

reaction arrow
CH3(CH2)3CH3
pentane

reaction arrow
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

Close this tab to return to the textbook.