Review pre-final
1. What product would you expect for the reaction of 1,2-epoxypropane with ethylmagnesium bromide after
aqueous workup?
H 2O
+ C2H5MgBr ?
O
A. 2-pentanol
B. 2-methyl-1-butanol
C. 3-methyl-1-butanol
D. 2,3-epoxypentane
E. ethyl isopropyl ether
2. The reaction of methyl acetate with two moles of methylmagnesium bromide, as shown below,
followed by aqueous workup, results in the formation of two alcohols. Which ones?
O
1. CH3MgBr (2 moles)
CH3 C OCH3
2. H2O
A. methanol and tert-butanol
B. ethanol and 3-pentanol
C. methanol and 3-methyl-3-pentanol
D. ethanol and tert-butanol
E. methanol and 2-pentanol
3. You treat 1,2-epoxycyclohexane with sodium borohydride, followed by aqueous work-up. What do
you expect?
A. cis-1,2-cyclohexanediol
B. a mixture of (R,R)-1,2-cyclohexanediol and (R,S)-1,2-cyclohexanediol
C. a mixture of (R,R)-1,2-cyclohexanediol and (S,S)-1,2-cyclohexanediol
D. (S,S)-1,2-cyclohexanediol
E. cyclohexanol
4. The diene below is unreactive towards dienophiles. What is the primary reason?
A. Because one of the double bonds are part of an aromatic ring
B. Because the double bonds are isolated
C. Because the double bonds are cumulated
D. Because it has difficulty adopting the s-cis conformation needed to react
E. Because it is too electron-rich
, 5. Lithium aluminum hydride can reduce many compounds, but not…
A. esters
B. ketones
C. alkenes
D. aldehydes
E. carboxylic acids
6. Jones’ reagent can oxidize many compounds, but not…
A. methanol
B. ethanol
C. 2-propanol
D. formaldehyde
E. 2-methyl-2-butanol
7. What is the most appropriate name for the compound below?
A. 1,5-dinitrotoluene
B. meta-dinitrotoluene
C. 1,3-dinitro-4-methylbenzene
D. 2,6-dinitrotoluene
E. 1,5-dinitro-2-toluene
8. How could the ether below be prepared?
A. by reacting sodium ethoxide with bromobenzene
B. by reacting sodium phenoxide (the sodium salt of phenol) with ethene
C. by reacting sodium phenoxide (the sodium salt of phenol) with bromoethane
D. by oxidizing ethylbenzene with chromic acid
E. by oxidizing ethylbenzene with potassium permanganate
9. How many of the following compounds are aromatic? The all abide by Huckel’s rule.
A. Only one
B. two
C. three
D. four
E. all
1. What product would you expect for the reaction of 1,2-epoxypropane with ethylmagnesium bromide after
aqueous workup?
H 2O
+ C2H5MgBr ?
O
A. 2-pentanol
B. 2-methyl-1-butanol
C. 3-methyl-1-butanol
D. 2,3-epoxypentane
E. ethyl isopropyl ether
2. The reaction of methyl acetate with two moles of methylmagnesium bromide, as shown below,
followed by aqueous workup, results in the formation of two alcohols. Which ones?
O
1. CH3MgBr (2 moles)
CH3 C OCH3
2. H2O
A. methanol and tert-butanol
B. ethanol and 3-pentanol
C. methanol and 3-methyl-3-pentanol
D. ethanol and tert-butanol
E. methanol and 2-pentanol
3. You treat 1,2-epoxycyclohexane with sodium borohydride, followed by aqueous work-up. What do
you expect?
A. cis-1,2-cyclohexanediol
B. a mixture of (R,R)-1,2-cyclohexanediol and (R,S)-1,2-cyclohexanediol
C. a mixture of (R,R)-1,2-cyclohexanediol and (S,S)-1,2-cyclohexanediol
D. (S,S)-1,2-cyclohexanediol
E. cyclohexanol
4. The diene below is unreactive towards dienophiles. What is the primary reason?
A. Because one of the double bonds are part of an aromatic ring
B. Because the double bonds are isolated
C. Because the double bonds are cumulated
D. Because it has difficulty adopting the s-cis conformation needed to react
E. Because it is too electron-rich
, 5. Lithium aluminum hydride can reduce many compounds, but not…
A. esters
B. ketones
C. alkenes
D. aldehydes
E. carboxylic acids
6. Jones’ reagent can oxidize many compounds, but not…
A. methanol
B. ethanol
C. 2-propanol
D. formaldehyde
E. 2-methyl-2-butanol
7. What is the most appropriate name for the compound below?
A. 1,5-dinitrotoluene
B. meta-dinitrotoluene
C. 1,3-dinitro-4-methylbenzene
D. 2,6-dinitrotoluene
E. 1,5-dinitro-2-toluene
8. How could the ether below be prepared?
A. by reacting sodium ethoxide with bromobenzene
B. by reacting sodium phenoxide (the sodium salt of phenol) with ethene
C. by reacting sodium phenoxide (the sodium salt of phenol) with bromoethane
D. by oxidizing ethylbenzene with chromic acid
E. by oxidizing ethylbenzene with potassium permanganate
9. How many of the following compounds are aromatic? The all abide by Huckel’s rule.
A. Only one
B. two
C. three
D. four
E. all
