Full file at https://fratstock.euMULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

1) Which of the following is a tertiary amine? 1)A)

B)

C)

D)

E)

Answer: D

2) There are 8 isomers that have the molecular formula C5H11Br. How many of these are tertiaryalkyl bromides?

2)

A) 2 B) 8 C) 1 D) 0 E) 3Answer: C

3) Which of the following is sec-butyl alcohol? 3)A) CH3CH(OH)CH2CH3B) (CH3)2CHOHC) (CH3)2CHOCH3D) (CH3)2CHCH2OHE) CH3CH2CH2CH2OH

Answer: A

1

Full file at https://fratstock.eu4) What is the common name for the following structure? 4)

A) IsobutaneB) IsopropylmethaneC) sec-ButaneD) t-ButaneE) n-Butane

Answer: A

5) Give the IUPAC name for the following structure: 5)

A) 2-methyl-3-ethylheptaneB) 5-IsopropyloctaneC) 4-IsopropyloctaneD) 3-ethyl-2-methylheptaneE) 2-methyl-3-propylheptane

Answer: C

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

6) There is something wrong with the following name. Write the structure and correct thename: 2-ethylpropane.

6)

Answer:

The correct name is 2-methylbutane.

7) Give structures for the three isomers with molecular formula C5H12 and provide thecommon name of each.

7)

Answer:

2

Full file at https://fratstock.eu8) Provide an acceptable name for the alkane shown below.

CH3CH2CH2CH2CH2CH3

8)

Answer: hexane or n-hexane

9) Provide an acceptable name for the alkane shown below. 9)

Answer: 2, 5-dimethylheptane

10) Provide an acceptable name for the alkane shown below. 10)

Answer: 5-sec-butyl-2, 2-dimethylnonane or2, 2-dimethyl-5-(1-methylpropyl) nonane

11) Provide an acceptable name for the alkane shown below. 11)

Answer: 4-isopropyldecane or 4-(1-methlyethyl) decane

12) Provide an acceptable name for the alkane shown below. 12)

Answer: 3-ethyl-6-methyl-5-propylnonane

3

Full file at https://fratstock.eu13) Provide an acceptable name for the alkane shown below. 13)

Answer: 3-ethyl-4, 4-dimethylheptane

14) Draw an acceptable structure for 4-t-butyloctane. 14)Answer:

15) Draw an acceptable structure for 3-ethyl-3-methylhexane. 15)Answer:

16) Draw an acceptable structure for 4-isopropyl-2-methylheptane. 16)Answer:

17) Draw an acceptable structure for 6-ethyl-2, 6, 7-trimethyl-5-propylnonane. 17)Answer:

4

Full file at https://fratstock.eu18) Provide an acceptable name for the alkane shown below. 18)

Answer: 2, 2, 3, 6-tetramethylheptane

19) Provide an acceptable name for the alkane shown below. 19)

Answer: 6-ethyl-2-methyl-5-propyldecane

20) Give the systematic name of the alkane shown below. 20)

Answer: 4-ethyl-2,2,7-trimethylnonane

21) Give the systematic name of the alkane shown below. 21)

Answer: 3-ethyl-4-isopropyloctane

5

Full file at https://fratstock.eu22) Give the systematic name of the cycloalkane shown below. 22)

Answer: 4-butyl-1,2-dimethylcyclohexane

23) Draw an acceptable structure for sec-butylcyclopentane. 23)Answer:

24) Provide the systematic name of the compound shown. 24)

Answer: 4-butyl-1-ethyl-2-methylcycloheptane

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

25) What is the common name for the following structure? 25)

A) Isobutyl bromideB) sec-Butyl bromideC) Neobutyl bromideD) t-Butyl bromideE) Isopropyl methyl bromide

Answer: D

6

Full file at https://fratstock.eu26) Give the IUPAC name for the following compound: 26)

A) 1-chloro-2-methylcyclohexaneB) 1-chloro-5-methylcyclohexaneC) 1-methyl-5-chlorocyclohexaneD) 1-methyl-2-chlorocyclohexaneE) 1, 2-chloromethylcyclohexane

Answer: A

27) Which of the following is diisopropyl ether? 27)A) CH3CH2CH2 O CH2CH2CH3B) (CH3)3COC(CH3)3C) (CH3)2CH)CH(CH3)2D)

E) CH3CH2CH2OCH(CH3)2Answer: C

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

28) Draw all ethers with molecular formula C4H10O. 28)

Answer:

29) Draw all possible constitutional isomers for C2H6O and give common names for eachstructure.

29)

Answer:

7

Full file at https://fratstock.euMULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

30) Give the IUPAC name for the following structure: 30)

A) 2-methyl-5-chlorocyclohexanolB) 5-chloro-2-methylcyclohexanolC) 2-methyl-3-chlorocyclohexanolD) 3-chloro-2-methylcyclohexanolE) 1-chloro-4-methylcyclohexanol

Answer: B

31) Which of the following compounds does not have the molecular formula C6H14O? 31)A) 1-hexanolB) 3-methyl-3-pentanolC) cyclohexanolD) 3-methyl-2-pentanolE) 2-hexanol

Answer: C

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

32) Give the structure of isopentyl alcohol. 32)Answer:

33) Provide the systematic name of the compound shown. 33)

Answer: 6,7-dimethyl-3-octanol

8

Full file at https://fratstock.eu34) Draw the structure of 3-chloro-N-ethyl-2-hexanamine. 34)

Answer:

35) Give the structure of tetramethylammonium chloride. 35)Answer:

36) Draw the structure of N-ethyl-5-methyl-3-hexanamine. 36)Answer:

37) Fluorine is more electronegative than chlorine yet the carbon-fluorine bond in CH3-F isshorter than CH3-Cl. Explain.

37)

Answer: Chlorine is a larger atom than fluorine and uses a 3p rather than 2p orbital. Theoverlap of a 2sp3 orbital with a 3p orbital is not as good as the overlap of a 2sp3orbital with a 2p orbital, causing the bond to be longer and weaker.

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

38) Which of the following will have the lowest boiling point? 38)A) CHCl3 B) CCl4 C) CH4 D) CH2Cl2 E) CH3Cl

Answer: C

39) Which of the compounds below will form hydrogen bonds between its molecules? 39)A) (CH3)3NB) CH3CH2OCH3C) CH3CH2CH2FD) ljCH3CH2CH2CH3E) CH3NHCH2CH3

Answer: E

9

Full file at https://fratstock.eu40) Which of the following has the greatest van der Waal's interaction between molecules of the same

kind?40)

A) CH3CH2CH2CH3B) CH3CH2CH2CH2CH3C)

D)

E)

Answer: B

41) Which of the following has the lowest boiling point? 41)A) CH3CH2CH2CH2CH2CH2CH3B) CH3CH2CH2CH2CH2CH3C)

D)

E)

Answer: E

42) Which of the following has the greatest solubility in CH3CH2CH2CH3? 42)A) CH3O- Na+

B) (CH3)3CHC) CH3OHD) CH3OCH3E) CH3NH2

Answer: B

10

Full file at https://fratstock.eu43) Which of the following is the most soluble in H2O? 43)

A) CH3CH2ClB) CH3OCH3C) CH3CHOD) CH3CH2CH3E) CH3CH2OH

Answer: E

44) Which of the following would have the highest boiling point? 44)A) CH3CH2 O CH2CH2 O CH3B) HO CH2CH2CH2CH2 OHC) CH3CH2 O CH2 O CH2CH3D) CH3 O CH2CH2CH2 O CH3E)

Answer: B

45) Consider the three isomeric alkanes n-hexane, 2, 3-dimethylbutane, and 2-methylpentane. Whichof the following correctly lists these compounds in order of increasing boiling point?

45)

A) 2-methylpentane < n-hexane < 2, 3-dimethylbutaneB) 2-methylpentane < 2, 3-dimethylbutane < n-hexaneC) n-hexane < 2, 3-dimethylbutane < 2-methylpentaneD) n-hexane < 2-methylpentane < 2, 3-dimethylbutaneE) 2, 3-dimethylbutane < 2-methylpentane < n-hexane

Answer: E

46) What is the strongest intermolecular force present in liquid ethanol? 46)A) induced dipole-induced dipoleB) ion-ionC) dipole-dipole, but not hydrogen bondingD) ion-dipoleE) dipole-dipole, specifically hydrogen bonding

Answer: E

47) Assuming roughly equivalent molecular weights, which of the following would have the highestboiling point?

47)

A) a quaternary ammonium saltB) a tertiary amineC) an alkyl chlorideD) an alcoholE) an ether

Answer: A

11

Full file at https://fratstock.euSHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

48) Explain why has a lower boiling point than CH3CH2CH2CH3. 48)

Answer: CH3CH2CH2CH3 has greater van der Waals forces because it has a greater contactarea than isobutane. Therefore, the boiling point of CH3CH2CH2CH3 is higher.

49) Primary and secondary amines exhibit hydrogen bonding; tertiary amines do not. Explain. 49)Answer: The nitrogen in a tertiary amine is not attached to a hydrogen. Recall that for a

molecule to exhibit hydrogen bonding it must have a hydrogen attached to a highlyelectronegative atom such as F, N, or O.

50) Explain why trimethylamine, (CH3)3N:, has a considerably lower boiling point thanpropylamine CH3CH2CH2NH2, even though both compounds have the same molecularformula.

50)

Answer: Since hydrogen bonding is possible for propylamine and not for trimethylamine,the boiling point is higher for propylamine.

51) Which of the molecules below has the higher boiling point? Briefly explain your choice.

CH3CH2CH2OH or CH3CH2OCH3

51)

Answer: CH3CH2CH2OH has the higher boiling point since it is capable of intermolecularhydrogen bonding.

52) Would you expect sodium chloride (NaCl) to be highly soluble in the organic solventhexane (CH3CH2CH2CH2CH2CH3)? Briefly explain your answer.

52)

Answer: One would not expect NaCl to be highly soluble in hexane. NaCl is an ionic solid(i.e., a very polar material) while hexane is nonpolar. Nonpolar solvent moleculesdo not solvate ions well. The attractions of oppositely charged ions to each other arevastly greater than the weak attractions of the ions for the solvent.

53) Which compound is more soluble in water? Briefly explain your choice.

CH3OCH3 or CH3CH2OH

53)

Answer: CH3CH2OH is more soluble in water since it can donate a hydrogen bond to waterand accept a hydrogen bond from water. CH3OCH3 can only accept a hydrogenbond from water; it has no hydrogen which can hydrogen bond to water.

54) Which compound is more soluble in water? Briefly explain your choice.

(CH3)2NH or CH3CH2CH3

54)

Answer: (CH3)2NH is more soluble in water since it can hydrogen bond with water. Alkanesare not capable of hydrogen bonding with water.

55) Which intermolecular force is primarily responsible for the interactions among alkanemolecules?

55)

Answer: Van der Waal's or London forces

12

Full file at https://fratstock.eu56) What is polarizability and how is it related to the size of an atom? 56)

Answer: Polarizability indicates the ease with which an electron cloud can be distorted. Thelarger the atom, the more loosely its nucleus holds the electrons in its outermostshell, and the more they can be distorted.

57) Arrange the following amines in order of increasing boiling point, lowest bp to highest bp:(CH3)2CHCH2CH2NH2, (CH3)2CHN(CH3)2, and (CH3)2CHCH2NHCH3.

57)

Answer: (CH3)2CHN(CH3)2 < (CH3)2CHCH2NHCH3 < (CH3)2CHCH2CH2NH2

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

58) The eclipsed and staggered forms of ethane are said to differ in: 58)A) conformation.B) constitution.C) structure.D) configuration.E) molecular formula.

Answer: A

59) Which of the following is the staggered conformation for rotation about the C1 C2 bond in thefollowing structure?

59)

A) I B) II C) III D) IV E) VAnswer: A

60) Among the butane conformers, which occur at energy minima on a graph of potential energyversus dihedral angle?

60)

A) eclipsed onlyB) gauche and antiC) anti onlyD) eclipsed and totally eclipsedE) gauche only

Answer: B

13

Full file at https://fratstock.eu61) Which of the following best explains the relative stabilities of the eclipsed and staggered forms of

ethane? The __________ form has the most __________ strain.61)

A) eclipsed; torsional B) staggered; torsionalC) eclipsed; steric D) staggered; steric

Answer: A

62) Which of the following best explains the reason for the relative stabilities of the conformersshown?

62)

A) II has more torsional strain. B) I has more torsional strain.C) II has more steric strain. D) I has more steric strain.

Answer: C

63) Which of the following statements about the conformers that result from rotation about the C2-C3bond of butane is correct?

63)

A) The highest energy conformer is one in which methyl groups are eclipsed by hydrogens.B) Steric strain is absent in the eclipsed forms.C) The gauche conformer is an eclipsed one.D) Torsional strain is absent in the eclipsed forms.E) none of the above

Answer: E

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

64) Draw the Newman projection that represents the most stable conformation of3,3-dimethylhexane viewed along the C3-C4 bond.

64)

Answer:

14

Full file at https://fratstock.eu65) Draw the Newman projection that represents the least stable conformation of

3,3-dimethylhexane viewed along the C3-C4 bond.65)

Answer:

66) Draw the Newman structure for the most stable conformation of 1-bromopropaneconsidering rotation about the C1-C2 bond.

66)

Answer:

67) Draw a Newman projection of the most stable conformation of 2-methylpropane. 67)Answer:

68) Define the term conformation. 68)Answer: Conformations are different arrangements of the same molecule formed by

rotations about single bonds.

69) Use a sawhorse structure to depict the eclipsed conformer of ethane. 69)Answer:

15

Full file at https://fratstock.eu70) View a butane molecule along the C2-C3 bond and provide a Newman projection of the

lowest energy conformer.70)

Answer:

71) Provide a representation of the gauche conformer of butane. 71)Answer:

72) Draw the Newman projection of the most stable conformation that results due to rotationabout the C2-C3 bond in 2,3-dimethylbutane.

72)

Answer:

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

73) Which of the following correctly ranks the cycloalkanes in order of increasing ring strain permethylene?

73)

A) cyclohexane < cyclopentane < cyclobutane < cyclopropaneB) cyclopentane < cyclobutane < cyclopentane < cyclopropaneC) cyclopropane < cyclobutane < cyclohexane < cycloheptaneD) cyclopentane < cyclopropane < cyclobutane < cyclohexaneE) cyclopropane < cyclopentane < cyclobutane < cyclohexane

Answer: A

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

74) Describe the source of angle strain and torsional strain present in cyclopropane. 74)Answer: The angle strain arises from the compression of the ideal tetrahedral bond angle of

109.5° to 60°. The large torsional strain occurs since all C-H bonds on adjacentcarbons are eclipsed.

16

Full file at https://fratstock.euMULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

75) Which of the following correctly lists the conformations of cyclohexane in order of increasingenergy?

75)

A) chair < twist-boat < boat < half-chairB) half-chair < boat < twist-boat < chairC) half-chair < twist-boat < boat < chairD) chair < boat < twist-boat < half-chairE) chair < twist-boat < half-chair < boat

Answer: A

76) Which of the following is the most stable conformation of bromocyclohexane? 76)

A) I B) II C) III D) IV E) VAnswer: C

77) In the boat conformation of cyclohexane, the "flagpole" hydrogens are located: 77)A) on C-1 and C-4.B) on adjacent carbons.C) on C-1 and C-3.D) on the same carbon.E) none of the above

Answer: A

78) Which conformer is at a local energy minimum on the potential energy diagram in the chair-chairinterconversion of cyclohexane?

78)

A) half-chairB) planarC) twist-boatD) fully eclipsedE) boat

Answer: C

17

Full file at https://fratstock.euSHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

79) Draw the chair conformer of cyclohexane. Label the axial hydrogens (Ha) and theequatorial hydrogens (He).

79)

Answer:

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

80) The Keq for the interconversion for the two chair forms of methylcyclohexane at 25 °C is 18. What% of the chair conformers feature an axial methyl group?

80)

A) 75 B) 50 C) 25 D) 5 E) 95Answer: D

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

81) The equilibrium constant for the ring-flip of fluorocyclohexane is 1.5 at 25 °C. Calculatethe percentage of the axial conformer at the temperature.

81)

Answer: Keq =[eq][ax]

= 1.5

% axial =[ax]

[eq] +[ax] 100%

=[1]

[1.5] + [1] 100%

= 40%

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

82) Which of the following describes the most stable conformation oftrans-1-tert-butyl-3-methylcyclohexane?

82)

A) The tert-butyl group is equatorial and the methyl group is axial.B) Both groups are equatorial.C) Both groups are axial.D) The tert-butyl group is axial and the methyl group is equatorial.E) none of the above

Answer: A

18

Full file at https://fratstock.eu83) Name the compound shown below. 83)

A) cis-1,3-dichlorocyclohexaneB) trans-1,4-dichlorocyclohexaneC) trans-1,2-dichlorocyclohexaneD) trans-1,3-dichlorocyclohexaneE) cis-1,2-dichlorocyclohexane

Answer: A

84) Which of the following has two equatorial alkyl substituents in its most stable conformation? 84)A) cis-1,4-diethylcyclohexaneB) cis-1,2-dimethylcyclohexaneC) cis-1,3-diethylcyclohexaneD) 1,1-dimethylcyclohexaneE) trans-1,3-diethylcyclohexane

Answer: C

SHORT ANSWER. Write the word or phrase that best completes each statement or answers the question.

85) Draw the most stable conformation of trans-1-tert-butyl-3-methylcyclohexane. 85)Answer:

86) Draw the most stable conformer of cis-1-isopropyl-2-methylcyclohexane. 86)Answer:

87) Draw the most stable conformation of cis-1-isopropyl-2-methylcyclohexane. 87)Answer:

MULTIPLE CHOICE. Choose the one alternative that best completes the statement or answers the question.

88) How many constitutional isomers are possible for C6H14? 88)A) 4 B) 7 C) 6 D) 8 E) 5

Answer: E

19

Full file at https://fratstock.eu89) If an acyclic alkane hydrocarbon contains n carbon atoms, how many hydrogen atoms must it also

contain?89)

A) n - 2 B) 2n + 2 C) 2n D) n + 2 E) nAnswer: B

20