Practice
Practice
Practice
A) I, II B) I, III C) II, IV D) I, IV
4. Which of the following species cannot act as both a Brønsted-Lowry acid and base?
A) HCO3- B) HSO4- C) HO- D) H2PO4-
6. Which of the following statements about Brønsted-Lowry acids and bases is true?
A) Loss of a proton from a base forms its conjugate acid.
B) Loss of a proton from an acid forms its conjugate base.
C) Gain of a proton by an acid forms its conjugate base.
D) Brønsted-Lowry acid-base reactions always result in the transfer of a proton from a
base to an acid.
8. Which of the following species is the conjugate base of the hydronium ion, H3O+?
A) H3O B) H2O- C) H2O D) HO-
A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) I B) II C) III D) IV
20. Which of the following ranks the compounds in order of increasing basicity, putting the
least basic first?
A) CH3NH2 < CH3OH < CH4 C) CH4 < CH3NH2 < CH3OH
B) CH3OH < CH3NH2 < CH4 D) CH4 < CH3OH < CH3NH2
21. Consider the following molecule with protons labeled, I-III. Rank these protons in
order of decreasing acidity, putting the most acidic first.
A) I > II > III B) I > III > II C) III > II > I D) III > I > II
22. Rank the following compounds in order of increasing acidity, putting the least acidic
first.
23. Rank the following compounds in order of increasing acidity, putting the least acidic
first.
25. Rank the following compounds in order of decreasing acidity, putting the most acidic
first.
26. Rank the following conjugate bases in order of increasing basicity, putting the least
basic first.
A) II < I < III B) II < III < I C) I < II < III D) I < III < II
27. Rank the following conjugate bases in order of decreasing basicity, putting the most
basic first.
A) II > I > III B) I > II > III C) III > I > II D) III > II > I
30. What is the direction of equilibrium when acetylene (C2H2) reacts with ethoxide
(CH3CH2O-) in an acid-base reaction?
31. Which of the following statements explain why H2O is a stronger acid than CH4?
A) H2O can form hydrogen bonds while CH4 cannot.
B) H2O forms a less stable conjugate base, HO-.
C) CH4 forms a more stable conjugate base, CH3-.
D) H2O forms a more stable conjugate base, HO-.
32. Which of the following statements explain why HBr is a stronger acid than HF?
A) Br- is more stable than F- because Br- is larger than F-.
B) Br- is less stable than F- because Br- is larger than F-.
C) Br- is more stable than F- because Br- is less electronegative than F-.
D) Br- is less stable than F- because Br- is less electronegative than F-.
34. Which of the following concepts can be used to explain the difference in acidity
between acetic acid (CH3COOH) and ethanol (CH3CH2OH)?
A) Hybridization B) Electronegativity C) Resonance D) Size
35. Which of the following concepts can be used to explain the difference in acidity
between acetylene (C2H2) and ethylene (C2H4)?
A) Size B) Resonance C) Inductive effect D) Hybridization
36. Which of the following concepts can be used to explain the difference in acidity
between ethanol (CH3CH2OH) and 2-fluoroethanol (FCH2CH2OH)?
A) Size B) Inductive effect C) Resonance D) Hybridization
37. Rank the following compounds in order of decreasing acidity, putting the most acidic
first.
A) I > II > III B) III > II > I C) II > III > I D) III > I > II
40. Which of the following is a Lewis acid but not a Brønsted-Lowry acid?
A) CH3OH B) H2O C) CH3COOH D) BF3
41. Which of the following species can be both Lewis acid and Lewis base?
CH3-O-CH3
A) Brønsted-Lowry acid and Lewis acid. C) Brønsted-Lowry base.
B) Brønsted-Lowry base and Lewis base. D) Lewis base.
A) I B) II C) III D) IV
44. Identify the Lewis base in the following reaction.
A) I B) II C) III D) IV
3. What is the molecular formula of an alkane that has twenty-three carbon atoms?
A) C23H46 B) C23H48 C) C23H50 D) C23H44
4. What is the molecular formula of a cycloalkane that has six carbon atoms?
A) C6H14 B) C6H10 C) C6H12 D) C6H16
5. What is the approximate C-C-C bond angle in propane?
A) 90° B) 109.5° C) 120° D) 180°
7. How many constitutional isomers are there with the molecular formula C5H12?
A) 2 B) 3 C) 4 D) 5
8. How many constitutional isomers are there with the molecular formula C6H14?
A) 2 B) 3 C) 4 D) 5
A) I B) II C) III D) IV
10. Which of the following compounds has primary, secondary, tertiary and quaternary
carbon atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
11. Which of the following compounds has only primary and secondary carbon atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,3,3-Trimethylpentane
12. Which of the following compounds has only primary, secondary and tertiary carbon
atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
13. Which of the following compounds has only primary, secondary and quaternary carbon
atoms?
A) Pentane C) 2,2-Dimethylpentane
B) 2-Methylpentane D) 2,2,3-Trimethylpentane
14. Which of the following compounds has primary, secondary and tertiary hydrogen
atoms?
A) Pentane B) Hexane C) 2-Methylpentane D) 2,2-Dimethylpentane
15. Which of the following compounds has only primary and secondary hydrogen atoms?
A) 2-Methylpentane C) 3-Methylpentane
B) 2,2,3-Trimethylpentane D) 2,2-Dimethylpentane
16. How many cycloalkane constitutional isomers (excluding stereoisomers) are there with
molecular formula C5H10?
A) 2 B) 3 C) 4 D) 5
19. What is the name of the alkyl group that contains two carbons in a straight chain and
one-carbon branch?
A) Ethyl B) Propyl C) Isopropyl D) None of the above
A) 4-Ethyl-5-methyloctane C) 4-Methyl-3-propylheptane
B) 4-Methyl-5-ethyloctane D) 4-Methyl-5-propyloctane
A) 3,5-Diethyl-6-methylheptane C) 3-Ethyl-5-isopropylheptane
B) 3,5-Diethyl-2-methylheptane D) 5-Ethyl-3-isopropylheptane
22. What is the IUPAC name for the following compound?
A) 2,3-Dimethyl-4-sec-butylheptane C) 3,5,6-Trimethyl-4-propylheptane
B) 4-sec-Butyl-2,3-dimethylheptane D) 2,3,5-Trimethyl-4-propylheptane
A) 5-Ethyl-3,6-dimethylheptane C) 3-Ethyl-2,5-dimethyloctane
B) 3-Ethyl-2,5-dimethylheptane D) 5-Ethyl-3,6-dimethyloctane
A) 2,3,5-Trimethylhexane C) 2,4-Diethyl-5-methylheptane
B) 2,4,5-Triethylhexane D) 4-Ethyl-3,6-dimethyloctane
A) 3-Ethyl-2,7-dimethyl-5-sec-butyldecane
B) 5-sec-Butyl-3-ethyl-2,7-dimethyldecane
C) 2,7-Dimethyl-3-ethyl-5-sec-butyldecane
D) 3-Ethyl-2,7-dimethyl-5-isobutyldecane
A) 3-Ethyl-1-methylcyclohexane C) 1-Ethyl-3-methylhexane
B) 1-Ethyl-3-methylcyclohexane D) 3-Ethyl-1-methylhexane
27. What is the IUPAC name for the following compound?
A) 1-sec-Butyl-4-isopropyl-2-methylcyclohexane
B) 1-Isopropyl-3-methyl-4-sec-butylcyclohexane
C) 4-Isopropyl-2-methyl-1-sec-butylcyclohexane
D) 1-sec-Butyl-3-isopropyl-2-methylcyclohexane
A) 1,4-Dimethylcyclohexane C) 1,3-Dimethylcyclopentane
B) 1,3-Dimethylcyclohexane D) 1,4-Dimethylcyclopentane
A) 1-Butylcyclohexane C) 1-Cyclohexylbutane
B) Cyclohexanebutane D) Butylcyclohexane
A) Hexylcyclopentane C) 1-Cyclopentylhexane
B) 1-Hexylcyclopentane D) 1-Cyclopentylheptane
A) 1-Butyl-3-methylcyclohexane C) 1-Methyl-3-sec-butylcyclohexane
B) 1-sec-Butyl-3-methylcyclohexane D) 1-sec-Butyl-3-methylhexane
32. What is the common name of the following alkyl group?
34. Rank the following alkanes in order of decreasing boiling point, putting the alkane with
the highest boiling point first.
A) I > II > III B) I > III > II C) II > III > I D) III > II > I
35. Rank the following alkanes in order of increasing melting point, putting the alkane with
the lowest melting point first.
A) I < III < II B) I < II < III C) II < III < I D) III < II < I
36. Which of the following statements about the conformations of acyclic alkanes is true?
A) Conformations are the same arrangements of atoms that cannot be interconverted
by rotation about single bonds.
B) In the eclipsed conformation, the C-H bonds on one carbon bisect the H-C-H bond
angle on the adjacent carbon.
C) In the staggered conformation, the C-H bonds on one carbon are directly aligned
with the C-H bonds on the adjacent carbon.
D) Rotating the atoms on one carbon by 60° converts an eclipsed conformation into a
staggered conformation, and vice versa.
37. Which of the following statements about the conformations of acyclic alkanes is not
true?
A) The staggered and eclipsed conformations are equally stable.
B) The staggered conformations are more stable than the eclipsed conformations.
C) An energy minimum and maximum occur every 60° as the conformation changes
from staggered to eclipsed.
D) Conformations that are neither staggered nor eclipsed are intermediate in energy.
38. Which of the following statements about the conformations of acyclic alkanes is true?
A) A staggered conformation with two larger groups 180° from each other is called
gauche.
B) Staggered conformations are at energy maxima and eclipsed conformations are
energy minima.
C) A staggered conformation with two larger groups 60° from each other is called
anti.
D) Gauche conformations are generally higher in energy than anti conformations.
A) I B) II C) III D) IV
A) I B) II C) III D) IV
43. Rank the conformers of butane in order of decreasing stability, putting the most stable
first.
A) I B) II C) III D) IV
A) I B) II C) III D) IV
46. Which of the following cycloalkanes has the most angle strain?
A) Cyclopropane B) Cyclobutane C) Cyclopentane D) Cyclohexane
47. Which of the following cycloalkanes has the least angle strain?
A) Cyclopropane B) Cyclohexane C) Cyclopentane D) Cycloheptane
A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) I B) II C) III D) IV
A) I B) II C) III D) IV
52. Select the most stable conformer of cis-1,3-cyclohexanediol.
A) I B) II C) III D) IV
A) I B) II C) III D) IV
54. Which of the following is the most stable conformation of the following compound?
A) I B) II C) III D) IV
55. Rank the conformers of 1,2,4-trimethylcyclohexane in order of decreasing stability,
putting the most stable first.
A) Stereoisomers C) Identical
B) Constitutional isomers D) Not isomers, different compounds
13. Which of the following is the correct definition for a pair of enantiomers?
A) A pair of stereoisomers that have a plane of symmetry.
B) A pair of stereoisomers that are not mirror images of each other.
C) A pair of stereoisomers that are not superimposable mirror images of each other.
D) A pair of stereoisomers that are superimposable mirror images of each other.
14. Which of the following molecules has a plane of symmetry?
A) I B) II C) III D) IV
I. cis-1,3-Dibromocyclohexane
II. 1-Bromo-1-methylcyclohexane
III. trans-1-Bromo-3-methylcyclohexane
IV. cis-1-Bromo-3-methylcyclohexane
A) I, II B) II, III C) I, IV D) III, IV
I. 2-Chlorobutane
II. 3-Bromopentane
III. 1-Bromo-2-methylpropene
IV. 2-Bromo-3-methylbutane
A) I, II B) I, IV C) II, III D) III, IV
20. How many stereogenic centers are present in ephedrine, a bronchodilator and
decongestant?
A) 0 B) 1 C) 2 D) 3
21. How many stereogenic centers are present in the following compound?
A) 0 B) 1 C) 2 D) 3
22. How many stereogenic centers are present in fructose, a simple sugar?
A) 1 B) 2 C) 3 D) 4
23. How many stereogenic centers are present in the following compound?
A) 1 B) 2 C) 3 D) 4
A) 1 B) 2 C) 3 D) 4
25. How many stereogenic centers are present in the following compound?
A) 1 B) 2 C) 3 D) 4
26. How many stereogenic centers are present in the following molecule?
A) 1 B) 2 C) 4 D) 5
27. How many stereoisomers are possible for a molecule with formula
CH3CHBrCH(OH)CH3?
A) 1 B) 2 C) 3 D) 4
28. How many stereoisomers can be drawn for a molecule with formula
CH3CH(OH)CH(OH)CH3?
A) 1 B) 2 C) 3 D) 4
29. What is the total number of possible stereoisomers for the following molecule?
A) 2 B) 4 C) 6 D) 8
30. How many isomers can be drawn (constitutional and stereoisomers) for
dimethycyclopropane?
A) 2 B) 3 C) 4 D) 6
32. How many stereogenic centers are present in gabapentin, used clinically to treat seizures
and certain types of chronic pain?
A) 0 B) 1 C) 2 D) 3
33. How many stereogenic centers are present in the following compound?
A) 0 B) 1 C) 2 D) 3
34. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-
Prelog system.
36. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-
Prelog system.
37. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-
Prelog system.
38. Rank the following groups in order of decreasing priority according to the Cahn-Ingold-
Prelog system.
40. Which of the following structures has a different configuration from the other three?
A) I B) II C) III D) IV
41. Which of the following structures has a different configuration from the other three?
A) I B) II C) III D) IV
54. Which of the following statements about meso compounds is not true?
A) A meso compound generally has a plane of symmetry.
B) A meso compound and its mirror image are identical.
C) A meso compound is achiral.
D) A meso compound is chiral.
A) I B) II C) III D) IV
A) I B) II C) III D) IV
61. How many isomers (constitutional and stereoisomers) exist for dimethylcyclobutane?
A) 3 B) 4 C) 5 D) 6