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Carbonyl Reaction Products

In each product answer box enter a single letter, selected from the list at the bottom of the page, designating the expected product.

Reactant Reagent Product Answer
Evaluation		 Response Box
(CH3)2CHCOCH3
3-methyl-2-butanone		 Jones' reagent
reaction arrow
CrO3 in H3O(+)

NaBH4 (in CH3OH)
reaction arrow
i) C6H5MgBr (in ether)
reaction arrow
ii) H3O(+)
i) C2H5OH (excess)
reaction arrow
ii) Acid catalyst, heat (–H2O)
i) (CH2)5NH (piperidine)
reaction arrow
ii) Acid catalyst, heat (–H2O)
N2H4 (hydrazine)
reaction arrow
KOH, heat
(CH3)2CHCH2CHO
3-methylbutanal		 Jones' reagent
reaction arrow
CrO3 in H3O(+)

NaBH4 (in CH3OH)
reaction arrow
i) C6H5MgBr (in ether)
reaction arrow
ii) H3O(+)
i) C2H5OH (excess)
reaction arrow
ii) Acid catalyst, heat (–H2O)
i) (CH2)5NH (piperidine)
reaction arrow
ii) Acid catalyst, heat (–H2O)
N2H4 (hydrazine)
reaction arrow
KOH, heat
CH3CH2COCH2CH3
3-pentanone		 Jones' reagent
reaction arrow
CrO3 in H3O(+)

NaBH4 (in CH3OH)
reaction arrow
i) C6H5MgBr (in ether)
reaction arrow
ii) H3O(+)
i) C2H5OH (excess)
reaction arrow
ii) Acid catalyst, heat (–H2O)
i) (CH2)5NH (piperidine)
reaction arrow
ii) Acid catalyst, heat (–H2O)
N2H4 (hydrazine)
reaction arrow
KOH, heat

A. (CH3)2CHCH(OH)CH3
  3-methyl-2-butanol		 B. C6H5C(OH)(C2H5)2
  3-phenyl-3-pentanol		 C. (CH3)2CHC(OC2H5)2CH3
  2,2-diethoxy-3-methylbutane		 D. (CH3)2CHCH2CO2H
  3-methylbutanoic acid
E. (CH3)2CHC(OH)(C6H5)CH3
  3-methyl-2-phenyl-2-butanol		 F. C6H5CH(OH)CH2CH(CH3)2
  3-methyl-1-phenyl-1-butanol		 G. (CH3)2CHCH2CH(OC2H5)2
  1,1-diethoxy-3-methylbutane		 H. (C2H5)2C(OC2H5)2
  3,3-diethoxypentane
I. (CH3)2CHCH2CH2OH
  3-methyl-1-butanol		 J. C2H5CH(OH)C2H5
  3-pentanol		 K. (CH3)2CHCH2CH3
  2-methylbutane		 L. CH3(CH2)3CH3
  pentane
M.
Enamine formation mechanism: aldehyde plus secondary amine via iminium and proton shift to stereoisomeric enamines		 N.
Enamine from 3-pentanone and piperidine: 1-(pent-2-en-3-yl)piperidine, ethyl and methyl on the C=C		 O.
Enamine from 3-methyl-2-butanone and piperidine: 1-(3-methylbut-1-en-2-yl)piperidine		 P.
  No Reaction

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