1.
A)
B)
C)
D)
E)
A correct IUPAC name for the following compound is:
2,5-Dimethyl-3-propylheptane
3,6-Dimethyl-5-propylheptane
6-Methyl-4-(1-methylethyl)octane
2-Methyl-3-(2-methylbutyl)hexane
3-Methyl-5-(1-methylethyl)octane
2.
A)
B)
C)
D)
E)
A correct IUPAC name for the following compound is:
4-propyl-5-chloro-3-heptanol
4-propyl-3-chloro-5-heptanol
4-(1-chloropropyl)-3-heptanol
5-chloro-4-propyl-3-heptanol
3-hydroxy-4-propyl-5-chloroheptane
3.
A)
B)
C)
D)
E)
Which of the following is bicyclo[3.2.2]nonane?
I
II
III
I
II
IV
V
IV
V
III
OH
Cl
4.
A)
B)
C)
D)
E)
A correct name for the following compound is:
2-Methylbicyclo[4.3.0]nonane
1-Methylbicyclo[4.3.1]nonane
7-Methylbicyclo[4.3.0]nonane
2-Methylbicyclo[4.3.1]nonane
1-Methylbicyclo[4.3.0]nonane
5.
A)
B)
C)
D)
E)
A correct IUPAC name for the following compound is:
3,6,7-trimethyl-4-bromo-1-octene
4-bromo-3-methyl-6-isopropyl-1-heptene
4-bromo-3,6,7-trimethyl-1-octene
4-bromo-6-isopropyl-3-methyl-1-heptene
4-bromo-6-isopropyl-3,6-dimethyl-1-hexene
6.
A)
B)
C)
D)
E)
cis-1,3-Dibromocyclohexane is represented by structure(s):
I
Br
H
II
H
Br
Br
III
Br
II and III
H
H
I
II
I and II
Br
Br
H
H
Br
III
7.
A)
B)
C)
D)
E)
An IUPAC name for the group is:
Isopentyl
Isoamyl
sec-Butylmethyl
2-Methylbutyl
2-Ethylpropyl
8.
A)
B)
C)
D)
E)
The correct IUPAC name for the following compound is:
1-Hydroxy-3-sec-butylcyclopentane
3-sec-Butyl-1-cyclopentanol
1-sec-Butyl-3-cyclopentanol
4-sec-Butyl-1-cyclopentanol
3-Isobutyl-1-cyclopentanol
CH3CHCH2
CH2CH3
9. Isopentyl is the common name for which alkyl group?
CH3CH2CH2CH
A)
CH3CH2CHCH2
B)
CH3
CH3CHCH2CH2
C)
CH3
CH3CH2CH
D)
CH3
CH3
CH2CH3
E)
CH CCH
3
2
CH3
OH
10.
A)
B)
C)
D)
E)
What is the correct IUPAC name for the following compound?
3-Hydroxymethylhept-2-ene
2-(1-Methylethyl) hex-4-en-1-ol
5-(1-Methylethyl) hex-2-en-6-ol
5-Isopropyl-2,6-hexenol
HO
2-(1-Methylethyl) hept-4-en-1-ol
11. The preferred conformation of cis-1-tert-butyl-3-methylcyclohexane is the one
in which:
A) the tert-butyl group is axial and the methyl group is equatorial.
B) the methyl group is axial and the tert-butyl group is equatorial.
C) both groups are axial.
D) both groups are equatorial.
E) the molecule exists in a boat conformation.
12.
A)
B)
C)
D)
E)
Which cycloalkane has the largest heat of combustion per CH2 group?
I
II
I
II
III
III
IV
V
IV
V
13. The most stable conformation of 3-bromo-2-methylpentane, viewed through
the C-3—C-4 bond (i.e., C-3 in the front, C-4 in the back):
CH
H
A) I
Br
Br
H
H
Br
H
B) II
CH
H
H
H
H
CH
H
CH(CH )
C) III
CH(CH )
CH(CH )
I
II
III
D) IV
H
CH
H
Br
E) V
Br
CH(CH )
3
3
3
3 2
3 2
3 2
3
3 2
H
CH3
H
CH3
H
CH2CH3
IV
V
14. The most stable conformation for 1,2-ethanediol (ethylene glycol) is shown
below. It is the most stable conformation because:
H
A) this corresponds to an anti conformation.
OH
B) in general, gauche conformations possess the minimum energy. H
C) it is stabilized by intramolecular hydrogen bonding.
H
OH
D) it is a staggered conformation.
H
E) it has the highest energy of all the possibilities.
15. The least stable conformation of cyclohexane is the:
A) boat.
B) twist boat.
C) chair.
D) half-chair.
E) twist chair.
16. To determine the parent name for an alkane, we begin by finding the
___________________________.
17. When more than one substituent is present on the parent chain, how do we
organize the names of the substituents in the name of the compound?
___________________________.
18. A compound containing a triple bond between the first two carbons in the
chain is called a ___________________________.
19. When non-bonded atoms/groups are closely positioned, the repulsive
interactions between their electron clouds are referred to as
___________________________.
20. What are the four possible parts of a IUPAC name?