### Carbonyl Reactions

Three isomeric carbonyl starting materials are available for your use. They are shown on the left below. Using one of these compounds, and selecting reagents from the list on the right, indicate how the products a) through o) might be prepared. Each question requires two responses. Under Carbonyl Cpd. enter 1, 2 or 3. Under Reagents enter a letter A through F, corresponding to your selection.

Carbonyl Cpd. |  | Reagents
--- | --- | ---

1. (CH3)2CHCOCH3
3-methyl-2-butanone
2. (CH3)2CHCH2CHO
3-methylbutanal
3. CH3CH2COCH2CH3
3-pentanone

A. Jones' reagent CrO3 in H3O(+)

B.
C6H5MgBr
(in ether)
followed by H3O(+) workupC.
C2H5OH
(excess)
acid-catalyst, heat (–H2O)
D.
NaBH4
in CH3OHE.
(CH2)5NH
(piperidine)
acid-catalyst, heat (–H2O)F.
N2H4
KOH & strong heat

Carbonyl Compound | Reagent(s) |  | Product |  | Answer Evaluation
--- | --- | --- | --- | --- | ---
|  |  | a) C6H5CH(OH)CH2CH(CH3)2 3-methyl-1-phenyl-1-butanol |
|  |  | b) (CH3)2CHCH(OH)CH3 3-methyl-2-butanol
|  |  | c)
|  |  | d) C6H5C(OH)(C2H5)2 3-phenyl-3-pentanol
|  |  | e) (CH3)2CHC(OC2H5)2CH3 2,2-diethoxy-3-methylbutane
|  |  | f) (CH3)2CHC(OH)(C6H5)CH3 3-methyl-2-phenyl-2-butanol
|  |  | g) (C2H5)2C(OC2H5)2 3,3-diethoxypentane
|  |  | h) (CH3)2CHCH2CH2OH 3-methyl-1-butanol
|  |  | i) (CH3)2CHCH2CH3 2-methylbutane
|  |  | j) (CH3)2CHCH2CO2H 3-methylbutanoic acid
|  |  | k)
|  |  | l) CH3(CH2)3CH3 pentane
|  |  | m) (CH3)2CHCH2CH(OC2H5)2 1,1-diethoxy-3-methylbutane
|  |  | n) C2H5CH(OH)C2H5 3-pentanol
|  |  | o)

Carbonyl Cpd. |  | Reagents
--- | --- | ---

1. (CH3)2CHCOCH3
3-methyl-2-butanone
2. (CH3)2CHCH2CHO
3-methylbutanal
3. CH3CH2COCH2CH3
3-pentanone

A. Jones' reagent CrO3 in H3O(+)

B.
C6H5MgBr
(in ether)
followed by H3O(+) workupC.
C2H5OH
(excess)
acid-catalyst, heat (–H2O)
D.
NaBH4
in CH3OHE.
(CH2)5NH
(piperidine)
acid-catalyst, heat (–H2O)F.
N2H4
KOH & strong heat

This script written by William Reusch, Dept. of Chemistry, Michigan State University. Please send comments and corrections to whreusch@pilot.msu.edu.