1.

Two isomeric forms of a saturated hydrocarbon

(a) have the same structure.
(b) have different compositions of elements.
(c) have the same molecular formula.
(d) have a different content of the isotopes of hydrogen.
(e) react vigorously with one another

2.Which of the following hydrocarbons does not have isomers?

(a) C7H16 (b) C6H14 (c) C5H10 (d) C4H8 (e) C3H8

3.The name of the alkane isomer of cis-3-hexene is:

(a) 2-methylpentane ( b) 3-methylpentane
(c) n-hexane (d) 2,3-dimethylbutane (e) cyclohexane

4.How many aromatic isomers of dibromobenzene exist?

(a) 2 (b) 3 (c) 4 (d) 6 (e) 8

5.Which one of the following compounds is an isomer of CH 3CH2CH2CH2OH?

(a) CH3CH2CH2OH (b) CH3CH(OH)CH3
(c) CH3CH2CH2CHO (Note: This is one way to write an aldehyde.)
(d) CH3CH2CH2CH3 (e) none of the above

6.Which of the following compounds is a functional group isomer of C2H5OH, ethanol (ethyl alcohol)?
(a) ethanal, CH3CHO (b) acetic acid, CH3COOH
(c) diethyl ether, (C2H5)2O (d) dimethyl ether, (CH3)2O (e) propanol, C3H7OH

7.For which of the compounds below are cis-trans isomers possible?

CH3CH=CH2 CH3CH=CHCH2CH3 CH3CH=CHCH3
(1) (2) (3)
(a) only 2 (b) both 1 and 2 (c) both 2 and 3 (d) all three (e) only 3

8.Which of the following does NOT exhibit geometric isomerism? (Hint: draw them!)
(a) 4-octene (b) 2-pentene (c) 3-hexene (d) 2-hexene (e) 1-hexene

9.Which of the following compounds displays optical isomerism?

(a) CH2(OH)-CH2(OH) (b) CH3-CHCl-COOH (c) CH2=CHCl (d) CHCl=CHCl (e) CH3-O-
C2H5

10.How many isomeric alkanes of the molecular formula C 5H12 are there?
(a) 1 (b) 2 (c) 3 (d) 4 (e) 5

11.How many alcohols are structural isomers with the formula: C 5H11OH?
(a) 5 (b) 6 (c) 7 (d) 8 (e) 9
12.
What is the relationship between the structures shown?
 (a) structural isomers (b) geometric isomers (c) conformational structures
(d) identical structures (e) optical isomers
13.
Which of the following statements concerning conformations is (are) TRUE?
(1) Ethane has an infinite number of conformations.
(2) The eclipsed conformation of a molecule is slightly more stable and energetically favored
than the staggered conformation.
(3) A conformation is one specific geometry of a molecule.
(a) 1 only
(b) 2 only
(c) 1 and 2
(d) 2 and 3
(e) 1 and 3
14.
Which of the following statements is FALSE regarding the reaction between Cl2 and C2H6?
(a) It is a substitution reaction.
(b) The reaction will give a single product of C 2H5Cl.
(c) The reaction mechanism involves free radicals.
(d) The reaction can be initiated with either sunlight or heat.
(e) The first step in the mechanism is the cleavage of the Cl-Cl bond to give chlorine atoms.
15.
Which of the following will undergo an addition reaction with chlorine?
(a) CH3CH2CH2CH3
(b) CH3CH2CH=CHCH3
(c) C6H6
(d) CH3CH2COOH
(e) CH3CH2OH
16.
What is the expected product formed from the reaction between 2-butene and Cl 2?
(a) 1-chlorobutane
(b) 2-chlorobutane
(c) 2,3-dichlorobutane
(d) 2,2-dichlorobutane
(e) 3,3-dichlorobutane
17.
The reaction of ethyne with which of the following gives CH 2Br-CHBrCl?
(a) HCl, then HBr
(b) HCl, then Br2
(c) Cl2, then HBr
(d) Cl2, then Br2
(e) H2, then Br2
18.
Dehydration of an alcohol leads to the formation of an _____ .
 (a) alkene
(b) alkane
(c) alkyne
(d) alkyl halide
(e) aldehyde
19.
A reaction in which a carboxylic acid reacts with a base to form a salt and water is called _____ .
(a) ionization
(b) esterification
(c) hydrolysis
(d) saponification
(e) neutralization
20.
How many moles of sodium hydroxide will react with one mole of:

(a) 5
(b) 4
(c) 3
(d) 2
(e) 1
21.
Ethanol can be oxidized stepwise. What is the first stable intermediate product when ethanol is
oxidized with a mild oxidation agent?
(a) CH3COOH
(b) CO2
(c) CH3CHO
(d) CH3CH2OH
(e) CH3OCH3
22.
Which of the following alcohols forms a ketone when oxidized?
(a) 1-propanol
(b) methanol
(c) 2-methyl-2-propanol
(d) 2-propanol
(e) all of the above
23.
What is the sum of the coefficients in the balanced equation for the complete combustion of 2-
methylbutane? Use smallest whole number coefficients. Do not forget coefficients of 1.
(a) 10
(b) 13
(c) 17
(d) 20
(e) 23
24.
The organic starting materials for the preparation of an ester could be _______ .
(a) an acid and an alcohol
(b) a ketone and an alcohol
(c) an alkane and a ketone
(d) only an acid
(e) an amine and an acid
25.
Hydrolysis (saponification) of a fat would yield ______ .
(a) water and an alkene
(b) ethanol and propanoic acid
(c) glycerol and soap
(d) ethanol and a soap
(e) a triester of glycerol with fatty acids
26.
The segment -CH2CH2CH2CH2CH2CH2- represents the polymer named _______ .
(a) polybutylene
(b) polyhexene
(c) polypropylene
(d) polystyrene
(e) polyethylene

Answers:

1. (c) 2. (e) 3. (e) 4. (b) 5. (e) 6. (d) 7. (c) 8. (e) 9. (b) 10. (c) 11. (d) 12. (c) 13. (e) 14. (b) 15. (b) 16.
(c) 17. (b) 18. (a) 19. (e) 20. (e) 21. (c) 22. (d) 23. (d) 24. (a) 25. (c) 26. (e)

1. What is the IUPAC name for the following compound?

(a) 1,3-pentamethylpropane
(b) 1,1,3,3-tetramethylbutane
(c) 2,4,4-trimethylpentane
(d) 2,2,4-trimethylpentane
2. What is the IUPAC name for the following compound?
 (a) dimethylcyclohexane
(b) 1,3-dimethylcyclohexane
(c) cis-1,3-dimethylcyclohexane
(d) trans-1,3-dimethylcyclohexane
3. The most stable conformational isomer of cis-1-bromo-2-chlorocyclohexane will have...
(a) both halide atoms in axial positions.
(b) both halide atoms in equatorial positions.
(c) the bromine atom in an axial position and the chlorine atom in an equatorial position.
(d) the bromine atom in an equatorial position and the chlorine atom in an axial position.
4. The most stable conformational isomer of trans-1-ethyl-2-methylcyclohexane will be...

5. Which Newman projection shows the most stable conformation of the following compound?

6. Which of the following compounds would yield this energy-rotation diagram?

7. Which of the these compounds represents the major monochlorination isomer formed in the
following reaction?
8. How many dichlorinated isomers can be formed by the halogenation of CH3CH2CH2CH3 with Cl2
in the presence of light?
(a) 2
(b) 3
(c) 5
(d) 6

1
What is the relationship between 1-butene and cis-2-butene?
unrelated compounds
A)
constitutional isomers
B)
enantiomers
C)
diastereomers
D)

2
What is the relationship between trans-2-butene and cis-2-butene?
unrelated compounds
A)
constitutional isomers
B)
enantiomers
C)
diastereomers
D)

3
Determine the relationship between the two molecules shown.
 constitutional isomers
A)
enantiomers
B)
diastereomers
C)
identical molecules
D)

4
Determine the relationship between the two molecules shown.

constitutional isomers
A)
enantiomers
B)
diastereomers
C)
identical molecules
D)

5
Give all terms that describe compounds (a) and (b).

enantiomers
A)
diastereomers
B)
same compound
C)
 chiral molecules
D)

6
How many stereoisomers are there for the following structure?

1
A)
2
B)
3
C)
4
D)

7
Which of the following molecules exists as a pair of enantiomers?
2-Bromopropane
A)
1-Bromo-3-methylbutane
B)
2-Cyclohexen-1-ol
C)
cis-1,2-Dichlorocyclobutane
D)

8
Which of the following diols exists as a pair of enantiomers?
cis-1,3-Cyclohexanediol
A)
trans-1.3-Cyclohexanediol
B)
cis-1,4-Cyclohexanediol
C)
trans-1,4-Cyclohexanediol
D)

9
Which of the following is capable of existing as a pair of enantiomers?
 2-methylpropane
A)
2-methylpentane
B)
3-methylpentane
C)
3-methylhexane
D)

1
0 Which of the 7 isomers of dichlorocyclohexane possess a plane of symmetry?

cis-1,2; cis-1,3;
A)
1,1; cis-1,2; cis-1,3;
B)
cis-1,2; cis-1,3; cis-1,4;
C)
1,1; cis-1,2; cis-1,3; cis-1,4; trans-1,4
D)

1
1 Which of the following has a plane of symmetry?

cis-1,2-Dimethylcyclohexane
A)
trans-1,3-Dimethylcyclohexane
B)
1,3-Dimethylcyclohexene
C)
1,4-Dimethylcyclohexene
D)

1
2 What is the IUPAC name of the following molecule?

(3R,5S)-dibromohexane
A)
(2R,4R)-dibromohexane
B)
 (2R,4S)-dibromohexane
C)
(R,S)-dibromohexane
D)

1
3 Which of the following groups has the highest priority in the (R,S) system?

A)
–CH=CH2
B)
–CH2–CH3
C)

D)

1
4 What is the correct name for this molecule?

(2R,3R)-2-bromo-3-chlorobutane
A)
(2S,3R)-2-bromo-3-chlorobutane
B)
(2S,3S)-2-bromo-3-chlorobutane
C)
(2R,3S)-2-bromo-3-chlorobutane
D)

1
5 The respective configurations of a and b are:

(2R,3S) and (2R,3R)

 A)
(2S,3R) and (2S,3R)
B)
(2S,3S) and (2R,3R)
C)
(2S,3R) and (2S,3S)
D)

1
6 What is the specific rotation 20[ ]D of the following molecule?

+4.42o
A)
+0.442o
B)
+44.2o
C)
– 44.2o
D)

1
7 Which of the following physical properties differ for each of a pair of enantiomers?

solubility in ethanol
A)
direction of rotation of plane-polarized light
B)
boiling point and melting point
C)
index of refraction
D)

1
8 An optically active compound is composed of 75% of the (R) enantiomer and 25% of the (S)
enantiomer. The enantiomeric excess (ee) is equal to
87.5%.
 A)
75%.
B)
50%.
C)
37.5%.
D)

1
9 If a sample of 2-butanol has an enantiomeric excess of 60% of l-2-butanol, how much of each isomer
is present?
60% levorotatory and 40% dextrorotatory
A)
80% levorotatory and 20% dextrorotatory
B)
70% levorotatory and 30% dextrorotatory
C)
66% levorotatory and 34% dextrorotatory
D)

2
0 How many stereocenters are there in the following molecule?

0
A)
2
B)
3
C)
1
D)

2
1 Which of the following statements is TRUE?
To be diastereomers, a pair of molecules must have 2 or more chiral centers.
 A)
To be diastereomers, a pair of molecules must have at least 1 chiral center.
B)
To be diastereomers, a pair of molecules must be stereoisomers.
C)
To be diastereomers, a pair of molecules must be a racemate.
D)

2
2 Shikimic acid is an important natural product. How many stereoisomers are possible for shikimic
acid?

16
A)
8
B)
4
C)
2
D)

2
3 Consider the following two structures. What is their isomeric relationship to each other?

identical
A)
enantiomers
B)
diastereomers
C)
constitutional isomers
D)

2
4 Explain why the two stereoisomers of 1,4-dimethylcyclohexane are achiral?

because they are identical

A)
because they are enantiomers
B)
because they both have the same absolute configuration
C)
because there are no stereocenters present in either molecule
D)

2
5 How many stereoisomers are there for 1-ethyl-3-methylcyclohexane?

2
A)
3
B)
4
C)
6
D)

2
6 What is the relationship between (1R,2S)-dibromocyclohexane and (1S,2R)-dibromocyclohexane?

identical
A)
enantiomers
B)
diastereomers
C)
constitutional isomers
D)
2
7 What is the relationship between (1R,2S)-1-bromo-2-methylcyclohexane and (1S,2R)-1-bromo-2-
methylcyclohexane?
identical
A)
enantiomers
B)
diastereomers
C)
constitutional isomers
D)

2
8 Which of the following may be separated by ordinary physical methods?

a pair of identical molecules

A)
a pair of enantiomers
B)
a pair of diastereomers
C)
a pair of identical atoms
D)

2
9 Which of the following may be separated by ordinary physical methods?
(R)-3-bromo-1-butene and (S)-3-bromo-1-butene
A)
cis-2-bromo-2-butene and trans-2-bromo-2-butene
B)
(2R,3S)-1,2-dibromobutane and (2S,3R)-1,2-dibromobutane
C)
(R)-2-bromobutane and (S)-2-bromobutane
D)

3
0 Consider the following two stereoisomers. How are they different?
 They have different melting points.
A)
They rotate plane-polarized light in opposite directions.
B)
They have different solubilities in water.
C)
They have different indices of refraction
D)