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O
O
A)
B)
C)
D)
E)
(Lovastatin)
4
5
6
7
8
Cl
Cl
Br
Br
Cl
Br
Br
Cl
Cl
Br
A)
B)
C)
D)
E)
Cl
Br
Br
II
III
I
II
III
More than one of these
None of these
243
Br
Br
Br
Cl
Cl
Br
Cl
Br
Br
Cl
Cl
II
III
A)
B)
C)
D)
E)
I
II
III
More than one of the above
None of the above
CH3
Cl
Cl
CH3
H3C
CH2CH2CH3
CH2CH2CH3
CH2CH2CH3
II
III
CH2Cl
CH2CH2CH3
H3C
Cl
H
CH2CH2CH3
A)
B)
C)
D)
E)
Cl
IV
I, II and III, IV
I, II
III, IV
IV, V
None of the structures
244
CH3
Cl
Cl
CH3
H3C
C2H5
C2H5
II
III
C2H5
H3C
CH2Cl
Cl
A)
B)
C)
D)
E)
Cl
C2H5
H
C2H5
IV
I, II, III, IV and V
I, II, III and IV
I and II
III and IV
IV alone
8. What is the molecular formula for the alkane of smallest molecular weight which
possesses a stereogenic center?
A) C4H10
B) C5H12
C) C6H14
D) C7H16
E) C8H18
9. (R)-2-Chlorobutane is represented by:
H3 C
A)
B)
C)
D)
E)
Cl
CH3
CH3
Cl
CH3
H3C
CH2Cl
CH2CH3
Cl
H3C
Cl
CH2CH3
CH2CH3
CH2CH3
CH2CH3
II
III
IV
I
II
III
IV
V
245
CH3
H
H3 C
OH
OH
CH3
HO
OH
CH2CH3
CH2CH3
CH2CH3
CH3
II
III
IV
III and V
I, III, IV and V
I, IV and V
I and III
I, II, IV and V
CH3
F
H
Cl
Cl
CH3
CH3
II
III
A)
B)
C)
D)
E)
I
II
III
More than one of the above
None of the above
A)
B)
C)
D)
E)
CH2CH3
A)
B)
C)
D)
E)
Cl
CH2CH3
CH3
HO
Cl
Cl
CH3
CH3
II
III
I
II
III
More than one of the above
None of the above
246
CH3
CH3
Br
Br
H3C
Br
CH2CH3
CH2CH3
CH2CH3
II
III
A)
B)
C)
D)
E)
I
II
III
More than one of the above
None of the above
CH3
H
Br
H
CH3
I
A)
B)
C)
D)
E)
CH3
Br
H
II
CH3
H
Br
III
I
II
III
It does not have a non-superposable enantiomer.
Both II and III
15. What is the total number of compounds, stereoisomers included, designated by the
general name "dichlorocyclopentane"?
A) 4
B) 5
C) 7
D) 8
E) 9
16. Which of the following is NOT true of enantiomers? They have the same:
A) boiling point.
B) melting point.
C) specific rotation.
D) density.
E) chemical reactivity toward achiral reagents.
247
248
22. The compounds whose molecules are shown below would have:
CH2CH3
CH3
H
A)
B)
C)
D)
E)
CH2CH3
CH3
II
the same melting point.
different melting points.
equal but opposite optical rotations.
More than one of the above
None of the above
23. If a solution of a compound (30.0 g/100 mL of solution) has a measured rotation of +15
in a 2 dm tube, the specific rotation is:
A) +50
B) +25
C) +15
D) +7.5
E) +4.0
24. What can be said with certainty if a compound has [] 25 = -9.25 ?
D
A) The compound has the (S) configuration.
B) The compound has the (R) configuration.
C) The compound is not a meso form.
D) The compound possesses only one stereogenic center.
E) The compound has an optical purity of less than 100%.
25. In the absence of specific data, it can only be said that (R)2bromopentane is:
A) dextrorotatory (+).
B) levorotatory ().
C) optically inactive.
D) achiral.
E) analogous in absolute configuration to (R)2chloropentane.
26. An alkane which can exhibit optical activity is:
A) Neopentane
B) Isopentane
C) 3Methylpentane
D) 3Methylhexane
E) 2,3Dimethylbutane
249
25
D
28.
O
The reaction of
with H2/Ni forms:
A) 2-methylheptane
B) (R)-2-methyl-5-heptanol
C) (S)-6-methyl-3-heptanol
D) (R and S)-6-methyl-3-heptanol
E) Achiral 6,6-dimethyl-3-hexanol
H2
C
OH
CH3
H
H3C
HO
A)
B)
C)
D)
E)
CH2OH
CH2OH
CH3
OH
II
I
H
OH
CH3
OH
CH2OH
CH2OH
CH3
III
IV
I
II
III
IV
V
250
25
D
25
D
= +13.52,
= +6.76?
CH3
CH3
Cl
CH3
Cl
Cl
Cl
Cl
Cl
CH3
CH3
CH3
II
III
A)
B)
C)
D)
E)
I
II
III
Both II and III
Both I and III
I
A)
B)
C)
D)
E)
Br
Br
H
Br
H
Br
Br
II
I
II
III
IV
Two of the above
Br
Br
H
III
Br
H3C
Br
A)
B)
C)
D)
E)
H
OH
CH3
IV
Br
H3C
CH3
OH
CH3
II
III
I
II
III
More than one of the above
None of the above
251
252
H3CS
D
I
A)
B)
C)
D)
E)
SCH3
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
HO
Br
Br
I
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
CH3
CH3
CH3
H
CH3
represent:
A) a single compound.
B) enantiomers.
C) meso forms.
D) diastereomers.
E) conformational isomers.
253
H
H
A)
B)
C)
D)
E)
and
H
Br
Br
are:
identical.
enantiomers.
diastereomers.
conformational isomers.
meso forms.
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
NH2
I
A)
B)
C)
D)
E)
NH2
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
254
OH
Cl
Cl
I
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
A)
B)
C)
D)
E)
Cl
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
255
H
H
F
F
A)
B)
C)
D)
E)
constitutional isomers.
enantiomers.
diastereomers.
identical.
stereoisomers.
A)
B)
C)
D)
E)
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
CH3
CH3
A)
B)
C)
D)
E)
structural isomers.
enantiomers.
diastereomers.
identical.
None of these
CH3
CH3
256
CH3
Cl
Br
Br
CH3
II
A)
B)
C)
D)
E)
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
A)
B)
C)
D)
E)
CH3
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
CH3
F
Cl
H
A)
B)
C)
D)
E)
H
CH3
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
257
II
A)
B)
C)
D)
E)
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
Br
H
Br
I
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
CH3
Cl
A)
B)
C)
D)
E)
H
H
Cl
CH3
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
258
CH3
H2N
CH3
H3C
A)
B)
C)
D)
E)
NH2
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
Cl
Cl
CH3
Cl
Cl
CH3
A)
B)
C)
D)
E)
CH3
enantiomers.
diastereomers.
constitutional isomers.
two different conformations of the same molecule.
not isomeric.
CH3
OH
A)
B)
C)
D)
E)
OH
H
H
CH3
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
259
OH
H
I
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
Cl
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
i-Pr
OH
OH
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
260
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
H
H
OH
Br
H
Br
H
CH3
CH3
A)
B)
C)
D)
E)
OH
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
The
Cl
H3CH2C
H
H
Cl
CH2CH3
A)
B)
C)
D)
E)
and
Cl
CH2CH3
Cl
are
CH2CH3
enantiomers.
diastereomers.
constitutional isomers.
two conformations of the same molecule.
not isomeric.
261
CH3
CH3
F
A)
B)
C)
D)
E)
H
H
constitutional isomers.
enantiomers.
diastereomers.
identical.
None of these
Br
OH
Br
I
A)
B)
C)
D)
E)
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
O
Cl
Cl
O
I
A)
B)
C)
D)
E)
OH
II
constitutional isomers.
enantiomers.
identical.
diastereomers.
not isomeric.
262
CH2OH
H
OH
CH3
HO
CH3
HO
CH3
HO
CH3
CH3
H
OH
H3C
CH3
OH
OH
II
III
IV
OH
CH3
HO
CH3
HO
CH3
HO
CH3
CH3
H
OH
H3C
CH3
OH
OH
II
III
IV
263