1. Draw line-angle pictures of each of the following (include dashes/wedges where
necessary to show stereochemistry).
(CH3)2CCHCH2CHO
H H
H H
H C C N C C H
H H H H H
3-bromo-2-methyl-2-hexene
(2R,3S)-2,3-dichloropentane
cis-1,3-dimethylcyclohexane
2. Fill in the labels s, p, d, f, sp, sp2, sp3, σ, or π as appropriate.
H
H3C
C O
3. For each pair, circle the lower energy species. If they are the same, write 'same'.
CH3
H
CH3
H
CH3
H
CH3
H3C
H
H
H
CH3
transition state for
a slower reaction
transition state for
a faster reaction
starting material in an
endothermic process
product in an
endothermic process
O
HO
O
O
O
OH
4. Label the relationship between each pair as identical, constitutional isomers,
enantiomers, diastereomers, or unrelated.
Cl
Cl
Cl
Cl
F
E-2-fluoro-2-pentene
5. Name this. Include steroechemistry.
Cl
6. Predict the major organic product or products for each of the following. Be sure to
include stereochemistry where important.
O
Br
Br
C N
Cl
O
Cl
OH
OH
HCl
(concentrated)
OH
H2SO4
(concentrated)
Cl
a) Mg
b) H2O
7. Predict the major organic product or products for each of the following. Be sure to
include stereochemistry where important.
H3CO
O
heat
O
heat
O
O
Br2
light
a) HB(Sia)2
b) H2O2, NaOH
a) BH3
b) H2O2, NaOH
H2
Pd/CaCO3/Pb
H2
Pd
8. Suggest reagents for each of the following
O
OH
O
Cl
O
OH
9. Suggest starting materials for each of the following.
a) CH3MgBr
b) H+
H2
Pd
a) Br2, light
b)
OH
10. Provide reagents for each step of this multi-step synthesis.
OH
O
11. Provide reagents for each step of this multi-step synthesis.
Br
OH
12. Give the product at each step of this multi-step synthesis.
N
Br2
a) O3
Li
light
b) DMS
13. Give the product at each step of this multi-step synthesis.
Li
Cl2
NH3(l)
H2O
14. Propose multi-step syntheses for these.
multiple steps
S
multiple steps
multiple steps
OCH3
OH
15. Suggest mechanisms for these transformations.
Br
OH
H2O
heat
Br
Br2
light
OH
O
NaOH
O
OH
1. Draw line-angle pictures of each of the following (include dashes/wedges where
necessary to show stereochemistry).
(CH3)2CCHCH2CHO
H H
O
H H
N
H C C N C C H
H
H H H H H
3-bromo-2-methyl-2-hexene
Br
Cl
(2R,3S)-2,3-dichloropentane
Cl
cis-1,3-dimethylcyclohexane
2. Fill in the labels s, p, d, f, sp, sp2, sp3, σ, or π as appropriate.
s
H
H3C
C O
s
σ
p
sp3
sp3
sp3
σ sp2
σ sp2
sp3 σ
σ
s
s
π
σ
sp2 sp2
p
sp2
sp2
3. For each pair, circle the lower energy species. If they are the same, write 'same'.
H
H
CH3
CH3
CH3
H
H3C
H
CH3
H
H
CH3
same
transition state for
a slower reaction
transition state for
a faster reaction
starting material in an
endothermic process
product in an
endothermic process
O
HO
O
O
O
OH
4. Label the relationship between each pair as identical, constitutional isomers,
enantiomers, diastereomers, or unrelated.
unrelated
diastereomer
Cl
Cl
enantiomer
Cl
Cl
F
E-2-fluoro-2-pentene
diastereomer
5. Name this. Include steroechemistry.
Cl
(2R,4R)-2-chloro-4-methylnonane
6. Predict the major organic product or products for each of the following. Be sure to
include stereochemistry where important.
O
Br
O
N
Br
C N
Cl
O
O
O
Cl
OH
OH
HCl
(concentrated)
OH
H2SO4
(concentrated)
Cl
a) Mg
b) H2O
Cl
7. Predict the major organic product or products for each of the following. Be sure to
include stereochemistry where important.
(±)
H3CO
O
heat
H3CO
O
O
O
heat
O
O
O
O
(±)
Br
Br2
light
a) HB(Sia)2
O
b) H2O2, NaOH
a) BH3
b) H2O2, NaOH
H2
Pd/CaCO3/Pb
H2
Pd
(±)
OH
8. Suggest reagents for each of the following
a) O3
O
b) DMS
OH
HCl
O
Cl
a) LiAlH4
O
b) H+
OH
9. Suggest starting materials for each of the following.
a) CH3MgBr
O
b) H+
H2
Pd
a) Br2, light
b)
OH
10. Provide reagents for each step of this multi-step synthesis.
a) NaNH2
H2
b)
Br
Lindlar
mCPBA
a) CH3MgBr
OH
O
b) H+
11. Provide reagents for each step of this multi-step synthesis.
Br
Br2
a) BH3
NaNH2
light
b) H2O2, NaOH
OH
12. Give the product at each step of this multi-step synthesis.
N
Br2
Br
a) O3
Li
light
O
O
b) DMS
13. Give the product at each step of this multi-step synthesis.
OH
(±)
Li
Cl2
NH3(l)
H2O
Cl
14. Propose multi-step syntheses for these.
multiple steps
a) NaNH2
b) CH3Br
H2
Lindlar's
Note, the order of the first
two steps could be
switched.
a) NaNH2
b) CH3CH2Br
S
multiple steps
Br2, light
H+
HSCH2CH3
Br
In step 2, any strong
bulky base.
Alternatively, you could
do an SN2 from the
bromocyclohexane.
N
Li
multiple steps
OCH3
OH
H+
CH3OH
Br2, light
Br
mCPBA
O
N
Li
Again, any strong base would be fine in step 2.
15. Suggest mechanisms for these transformations.
H Br
H
OH
H2O
heat
H
H H
H
H
O
H H H
O H
H
H
O
H
Br
Br2
light
Br
H
Br
2 Br
light
Br
Br
CH3
H
H
CH3
H
Br
CH3
Br
CH3
H
HBr
O H
O H
Br
O
NaOH
O
O H
O
O
H
O
O
O
H