Organic Chemistry 4th Edition By Janice Smith – Test Bank

 

 

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Sample Test

Chapter 3: Intro. to Organic Molecules & Functional Groups

 

1.	Which of the following lists contains common heteroatoms found in organic molecules?
	A)	N, O, S, P, Cl	C)	Na, Mg, S, N, Cl
	B)	Na, O, S, P, Cl	D)	Na, Mg, O, N, Cl

 

2.	Why do heteroatoms confer reactivity on a particular molecule?
	A)	Because they have lone pairs and create electron-rich sites on carbon.
	B)	Because they have lone pairs and create electron-deficient sites on carbon.
	C)	Because they are electronegative and act as electrophiles.
	D)	Because they are electropositive and act as nucleophiles.

 

3.	Why do p bonds confer reactivity on a particular molecule?
	A)	Because p bonds are difficult to break in chemical reactions.
	B)	Because p bonds make a molecule an acid.
	C)	Because p bonds are easily broken in chemical reactions.
	D)	Because p bonds make a molecule an electrophile.

 

4.	Which of the following molecules contain the same functional groups?
	A)  I, II, III    B)  I, II, IV    C)  II, III, IV    D)  I, III, IV

 

5.	Which of the following molecules contain the same functional groups?
	A)  I, II, IV    B)  I, II, III    C)  II, III, IV    D)  I, III, IV

 

6.	Which of the following molecules are aliphatic hydrocarbons?
	A)  I, II, III    B)  I and III    C)  II, III, IV    D)  II and IV

 

7.	Which of the following molecules are aromatic hydrocarbons?
	A)  I    B)  II    C)  III    D)  I and III

 

8.	Which of the following correctly matches the molecules to the names of the functional groups?   I. CH3OH Carboxylic acid II. CH3CO2CH3 Ester III. CH3COCH3 Ketone IV. H2CO Alcohol
	A)  I and II    B)  III and IV    C)  II and III    D)  II and IV

 

9.	Which of the following correctly matches the molecules to the names of the functional groups?   I. CH3OCH3 Ether II. CH3CONH2 Amine III. CH3SH Thiol IV. CH3CHO Alcohol
	A)  I and II    B)  II and III    C)  III and IV    D)  I and III

 

10.	Which of the following correctly matches the molecules to the names of the functional groups?   I. CH3NH2 Amide II. CH3SCH3 Sulfide III. CH3CONH2 Amine IV. CH3CO2CH3 Ester
	A)  I and II    B)  II and IV    C)  III and IV    D)  II and III

 

11.	Consider the molecule donepezil (used to treat Alzheimer’s disease).  Which of the following lists the correct functional groups present in donepezil?
	A)	Amide, aromatic, ether, ketone.	C)	Amine, aromatic, ester, ketone.
	B)	Amide, aromatic, ester, ketone.	D)	Amine, aromatic, ether, ketone.

 

12.	Consider the molecule atenolol (a b blocker used to treat hypertension).  Which of the following lists the correct functional groups present in atenolol?
	A)	Primary alcohol, amide, primary amine, aromatic, ether.
	B)	Secondary alcohol, amide, secondary amine, aromatic, ether.
	C)	Secondary alcohol, amide, primary amine, aromatic, ether.
	D)	Secondary alcohol, amide, secondary amine, aromatic, ester.

 

13.	Which of the following structures contains a secondary amine?
	A)  I    B)  II    C)  III    D)  IV

 

14.	Which of the following structures contains a primary amine?
	A)  I    B)  II    C)  III    D)  IV

 

15.	Which of the following structures contains an amide?
	A)  I    B)  II    C)  III    D)  IV

 

16.	Which of the following structures contains an alkene?
	A)  I    B)  II    C)  III    D)  IV

 

17.	Which of the following is a tertiary amine?
	A)  I    B)  II    C)  III    D)  IV

 

18.	Which of the following is a secondary alcohol?
	A)  I    B)  II    C)  III    D)  IV

 

19.	Which of the following statements best describes the relationship between the surface area of a molecule and the strength of the intermolecular forces?
	A)	The larger the surface area, the weaker the intermolecular force.
	B)	The larger the surface area, the stronger the intermolecular forces.
	C)	The smaller the surface area, the stronger the intermolecular forces.
	D)	There is no relationship between surface area and intermolecular forces.

 

20.	Rank the following compounds in order of increasing strength of intermolecular forces, putting the molecule with the weakest intermolecular force first.
	A)  I < II < III    B)  II < I < III    C)  I < III < II    D)  II < III < I

 

21.	Which of the following compounds has the lowest boiling point?
	A)  I    B)  II    C)  III    D)  IV

 

22.	Which of the following compounds has the highest boiling point?
	A)  I    B)  II    C)  III    D)  IV

 

23.	Which of the following compounds has the highest boiling point?
	A)  I    B)  II    C)  III    D)  IV

 

24.	Which of the following compounds has the highest boiling point?
	A)  I    B)  II    C)  III    D)  IV

 

25.	Which of the following compounds has the highest boiling point?
	A)  I    B)  II    C)  III    D)  IV

 

26.	Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.
	A)	I > II > III > IV	C)	III > II > IV > I
	B)	III > IV > II > I	D)	I > IV > II > III

 

27.	Which of the following compounds can form intermolecular hydrogen bonds with a molecule similar to itself?
	A)  I    B)  II    C)  III    D)  IV

 

28.	What is the strongest intermolecular force present in 1-propanol?
	A)	Ion-ion	C)	Dipole-dipole
	B)	Hydrogen bonding	D)	Induced dipole-induced dipole

 

29.	What intermolecular force is generally considered the strongest?
	A)	Hydrogen bonding	C)	Covalent bonds
	B)	London dispersion forces	D)	Dipole-dipole

 

30.	What intermolecular force is generally considered the weakest?
	A)	Hydrogen bonding	C)	Dipole-dipole
	B)	London dispersion forces	D)	Ion-ion

 

31.	Rank the following compounds in order of increasing melting point, putting the compound with the least melting point first.
	A)  II < I < III    B)  I < III < II    C)  I < II < III    D)  III < II < I

 

32.	Rank the following compounds in order of decreasing melting point, putting the compound with the highest melting point first.
	A)  I > II > III    B)  II > III > I    C)  III > II > I    D)  III > I > II

 

33.	Which of the following intermolecular forces would not form between similar molecules of the structure below?
	A)	London dispersion forces	C)	Hydrogen bonding
	B)	Ion-ion	D)	Dipole-dipole

 

34.	Which of the following alkanes is expected to have the highest melting point?
	A)  I    B)  II    C)  III    D)  IV

 

35.	Which of the following compounds is expected to be the least soluble in H2O?
	A)  I    B)  II    C)  III    D)  IV

 

36.	Which of the following compounds is expected to be the most soluble in H2O?
	A)  I    B)  II    C)  III    D)  IV

 

37.	Which of the following compounds would be expected to be more soluble in hexane (C6H14)?
	A)  I    B)  II    C)  III    D)  IV

 

38.	Which of the following statements about the solubility of organic compounds in H2O is true?
	A)	The non-polar part of a molecule that is not attracted to water is said to be hydrophilic.
	B)	The non-polar part of a molecule that is not attracted to water is said to be hydrophobic.
	C)	The polar part of a molecule that can hydrogen bond to water is said to be hydrophobic.
	D)	For an organic compound with one functional group that contains an O or N atom, the compound is water soluble only if it has ³ 5 carbons.

 

39.	Which of the following compounds is expected to be H2O soluble?
	A)  I    B)  II    C)  III    D)  IV

 

40.	What molecular features are required for soap to properly dissolve grease and oil?
	A)	The molecule must be large.
	B)	The molecule must contain a polar head.
	C)	The molecule must contain a non-polar tail.
	D)	B and C are required.

 

41.	Which of the following statements about vitamin A, drawn below, are true?
	A)	Vitamin A is soluble in H2O.
	B)	Vitamin A is insoluble in organic solvents.
	C)	Vitamin A contains an aromatic ring.
	D)	Vitamin A is insoluble in H2O.

 

42.	Which of the following statements about vitamin C, drawn below, are true?
	A)	Vitamin C is insoluble in H2O.
	B)	Vitamin C is soluble in H2O.
	C)	Vitamin C is an aliphatic hydrocarbon.
	D)	Vitamin C contains a ketone functional group.

 

43.	Which of the following could most likely serve as an ionophore?
	A)  I    B)  II    C)  III    D)  IV

 

44.	The indicated carbon atom is:
	A)	Electrophilic because it is electron-deficient.
	B)	Nucleophilic because it is electron-deficient.
	C)	Electrophilic because it is electron-rich.
	D)	Nucleophilic because it is electron-rich.

 

45.	The indicated bond is:
	A)	Nucleophilic because it is electron-deficient.
	B)	Electrophilic because it is electron-deficient.
	C)	Nucleophilic because it electron-rich.
	D)	Electrophilic because it is electron-rich.

 

46.	The indicated bond is:
	A)	Nucleophilic because it is electron-deficient.
	B)	Electrophilic because it is electron-rich.
	C)	Nucleophilic because it is electron-rich.
	D)	Electrophilic because it is electron-deficient.

 

47.	Which of the following list the correct functional groups found in aspartame, the artificial sweetener?
	A)	Amine, aromatic, carboxylic acid, ether, ketone.
	B)	Amine, amide, aromatic, carboxylic acid, ester.
	C)	Amide, alcohol, aromatic, carboxylic acid, ether.
	D)	Amine, aromatic, carboxylic acid, ester, nitrile.

 

48.	Rank the following compounds in order of decreasing boiling point, putting the compound with the highest boiling point first.
	A)	I > III > IV > II	C)	IV > I > II > III
	B)	IV > II > I > III	D)	I > IV > II > III

 

 

Answer Key

 

1.	A
2.	B
3.	C
4.	D
5.	A
6.	B
7.	D
8.	C
9.	D
10.	B
11.	D
12.	B
13.	C
14.	A
15.	D
16.	B
17.	B
18.	D
19.	B
20.	C
21.	D
22.	D
23.	B
24.	D
25.	A
26.	C
27.	D
28.	B
29.	A
30.	B
31.	C
32.	D
33.	B
34.	D
35.	A
36.	B
37.	A
38.	B
39.	B
40.	D
41.	D
42.	B
43.	D
44.	A
45.	C
46.	D
47.	B
48.	D

 

Chapter 4: Alkanes

 

1.	Which of the following statements about alkanes is not true?
	A)	Alkanes are aliphatic hydrocarbons.
	B)	Alkanes contain only C-C and C-H s bonds.
	C)	Alkanes are acyclic or cyclic.
	D)	Acyclic alkanes have two fewer H atoms than cyclic alkanes with the same number of carbons.

 

2.	Which of the following statements about alkanes is true?
	A)	Alkanes are aliphatic hydrocarbons having only C-C and C-H p bonds.
	B)	Cyclic alkanes have two fewer H atoms than acyclic alkanes with the same number of carbons.
	C)	Acyclic alkanes contain carbons joined in one or more rings.
	D)	Acyclic alkanes have general molecular formula CnH2n.

 

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°

 

6.	What is the hybridization of a carbon atom in an alkane?
	A)  sp3    B)  sp2    C)  sp    D)  p

 

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

 

9.	Which of the following is not another representation for 2-methylbutane?
	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

 

17.	What is the parent chain for the following compound?
	A)  Hexane    B)  Heptane    C)  Octane    D)  Nonane

 

18.	What is the parent chain for the following compound?
	A)  Heptane    B)  Octane    C)  Nonane    D)  Decane

 

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

 

20.	What is the IUPAC name for the following compound?
	A)	4-Ethyl-5-methyloctane	C)	4-Methyl-3-propylheptane
	B)	4-Methyl-5-ethyloctane	D)	4-Methyl-5-propyloctane

 

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

 

23.	What is the IUPAC name for the following compound?
	A)	5-Ethyl-3,6-dimethylheptane	C)	3-Ethyl-2,5-dimethyloctane
	B)	3-Ethyl-2,5-dimethylheptane	D)	5-Ethyl-3,6-dimethyloctane

 

24.	What is the IUPAC name for the following compound?
	A)	2,3,5-Trimethylhexane	C)	2,4-Diethyl-5-methylheptane
	B)	2,4,5-Triethylhexane	D)	4-Ethyl-3,6-dimethyloctane

 

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

 

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

 

28.	What is the IUPAC name for the following compound?
	A)	1,4-Dimethylcyclohexane	C)	1,3-Dimethylcyclopentane
	B)	1,3-Dimethylcyclohexane	D)	1,4-Dimethylcyclopentane

 

29.	What is the IUPAC name for the following compound?
	A)	1-Butylcyclohexane	C)	1-Cyclohexylbutane
	B)	Cyclohexanebutane	D)	Butylcyclohexane

 

30.	What is the IUPAC name for the following compound?
	A)	Hexylcyclopentane	C)	1-Cyclopentylhexane
	B)	1-Hexylcyclopentane	D)	1-Cyclopentylheptane

 

31.	What is the IUPAC name for the following compound?
	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?
	A)  Isobutyl    B)  sec-Butyl    C)  Isopropyl    D)  tert-Butyl

 

33.	What is the common name of the following alkyl group?
	A)  Isopropyl    B)  Isobutyl    C)  sec-Butyl    D)  tert-Butyl

 

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.

 

39.	Which of the following is not a conformer of butane?
	A)  I    B)  II    C)  III    D)  IV

 

40.	Which of the following are gauche conformers?
	A)  I and II     B)  I and III    C)  II and IV    D)  II and III

 

41.	Which of the following are anti conformers?
	A)  I and II    B)  II and III    C)  I and IV    D)  II and IV

 

42.	Which of the following conformers has the highest energy?
	A)  I    B)  II    C)  III    D)  IV