Exam Prep Organic Chemistry—structure 449 Ch.10 - Chemistry Canada 4e | Complete Test Bank by John A. Olmsted. DOCX document preview.
CHAPTER 10
ORGANIC CHEMISTRY – STRUCTURE
CHAPTER STUDY OBJECTIVES
1. Draw and name hydrocarbons using the IUPAC system.
SKILLS TO MASTER: Naming alkanes and alkyl groups; naming branched-chain alkanes; naming cycloalkanes, alkenes, and alkynes; naming other substituents
KEY CONCEPTS: The IUPAC system of nomenclature gives each compound a unique name.
2. Draw and name aromatic compounds using the IUPAC system.
SKILLS TO MASTER: Naming benzene compounds using numbers or the o-, m-, and p- designations to denote the locations of substituents
KEY CONCEPTS: All six carbon atoms in benzene are equivalent.
3. Draw and name compounds containing common functional groups.
SKILLS TO MASTER: Naming and drawing alkyl halides; naming and drawing alcohols; naming and drawing ethers; naming and drawing amines; naming and drawing aldehydes and ketones; naming and drawing carboxylic acids, esters, and amides; naming and drawing nitriles
KEY CONCEPTS: The IUPAC system can be used to unambiguously assign a name to any compound.
4. Recognize, name, and draw stereoisomers and conformations.
SKILLS TO MASTER: Naming cis and trans stereoisomers using the E/Z system; drawing structures with wedged and dashed bonds; drawing conformations using Newman projections; recognizing enantiomers and diastereomers; determining from a line structure whether a molecule is chiral or achiral Identifying R and S enantiomers
KEY CONCEPTS: Enantiomers are non-superimposable mirror images of each other. A compound is chiral if it contains a carbon atom bonded to four different groups.
Multiple Choice QUESTIONS
1. What is the correct name for the line structure shown below?
a) 2-methylhexane
b) 2-methylheptane
c) 5-methylhexane
d) 1,1-dimethylpentane
e) 2-butylpropane
Difficulty: Easy
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
2. What is the correct name for the structure below?
a) 2-ethylpentane
b) 2-propylbutane
c) 3-ethylpentane
d) 3-methylhexane
e) 4-methylhexane
Difficulty: Easy
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
3. What is the correct name for the structure below?
a) 1,1-dimethylheptan-3,5-diene
b) 6,6-dimethylheptan-1,3-diene
c) 6,6,6-trimethylhexan-1,3-diene
d) 1,1,1-trimethylhesan-3,5-diene
e) 6,6-dimethylhexane-1,3-diene
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
4. What is the correct name for the structure below?
a) propane
b) cyclobutane
c) cyclopropane
d) butane
e) isobutene
Difficulty: Easy
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
5. What is the correct name for the CH3CH2C(CH3)(CH2CH3)CH2CH2CH3?
a) nonane
b) 4-ethyl-4-methylhexane
c) 1-propyl-1-ethylbutane
d) 3-ethyl-3-methylhexane
e) 1-propyl-1ethyl-1-ethylpropane
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
6. What is the correct name for the structure below?
a) 1-methyl-3-ethylcyclopentane
b) 1-ethyl-3-methylcyclopentane
c) cycloctane
d) 1-ethyl-4-methylcyclopentane
e) 1-methyl-4-ethylcyclopentane
Difficulty: Easy
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
7. What is the correct name for the line structure shown below?
a) 3-chloroethylcyclopentane
b) 1-chloro-3-ethylcyclopentane
c) 4-chloroethylcyclopentane
d) 1-chloro-4-ethylcyclopentane
e) 3-chloroethylpentane
Difficulty: Easy
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
8. The IUPAC name for 
is
a) 6-ethyl-3,4-dimethylheptane.
b) 2-ethyl-4,5-dimethylheptane.
c) 3,4,6-trimethyloctane.
d) 3,5,6-trimethyloctane.
e) 2-(1-methylpropyl)-4-methylhexane.
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
9. An IUPAC name for 
is
a) 5-methyl-4-(1-methylpropyl)hexane.
b) 2-methyl-3-(1-methylpropyl)hexane.
c) 2-methyl-3-(2-methylpropyl)hexane.
d) 3-methyl-4-(1-methylethyl)heptane.
e) 5-methyl-4-(1-methylethyl)heptane.
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
10. A correct IUPAC name for the following compound is
a) 2,5-Dimethyl-3-propylheptane.
b) 3,6-Dimethyl-5-propylheptane.
c) 6-Methyl-4-(1-methylethyl)octane.
d) 2-Methyl-3-(2-methylbutyl)hexane.
e) 3-Methyl-5-(1-methylethyl)octane.
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
11. A correct IUPAC name for the following compound is
a) 4-propyl-5-chloro-3-heptanol.
b) 4-propyl-3-chloro-5-heptanol.
c) 4-(1-chloropropyl)-3-heptanol.
d) 5-chloro-4-propyl-3-heptanol.
e) 3-hydroxy-4-propyl-5-chloroheptane.
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
12. Which of the following is bicyclo[3.2.2]nonane?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
13. Select the systematic name for
a) cis-1,3-Dichlorocyclopentane
b) trans-1,4-Dichlorocyclopentane
c) cis-1,2-Dichlorocyclopentane
d) trans-1,3-Dichlorocyclopentane
e) 1,1-Dichlorocyclopentane
Difficulty: Medium
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
14. Which compound is bicycloheptane?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name hydrocarbons using the IUPAC system.
Section Reference: 10.1 Hydrocarbons
15. 4-amino-2-chlorophenol is
a) I.
b) II.
c) III.
d) IV.
e) V.
Difficulty: Medium
Learning Objective: Draw and name aromatic compounds using the IUPAC system.
Section Reference: 10.2 Aromatic Compounds
16. How many different dibromophenols are possible?
a) 8
b) 7
c) 6
d) 5
e) 4
Difficulty: Hard
Learning Objective: Draw and name aromatic compounds using the IUPAC system.
Section Reference: 10.2 Aromatic Compounds
17. The correct name for the compound below is
a) 3,4-Dibromoaniline.
b) 2,4-Dibromoaniline.
c) 2,5-Dibromoaniline.
d) 3,6-Dibromoaniline.
e) 2,6-Dibromoaniline.
Difficulty: Medium
Learning Objective: Draw and name aromatic compounds using the IUPAC system.
Section Reference: 10.2 Aromatic Compounds
18. Toluene is the name commonly assigned to
a) hydroxybenze.
b) aminobenzene.
c) methylbenzene.
d) ethylbenzene.
e) methoxybenzene.
Difficulty: Easy
Learning Objective: Draw and name aromatic compounds using the IUPAC system.
Section Reference: 10.2 Aromatic Compounds
19. Phenol is the name commonly assigned to
a) hydroxybenze.
b) aminobenzene.
c) methylbenzene.
d) ethylbenzene.
e) methoxybenzene.
Difficulty: Easy
Learning Objective: Draw and name aromatic compounds using the IUPAC system.
Section Reference: 10.2 Aromatic Compounds
20. Aniline is the name commonly assigned to
a) hydroxybenze.
b) aminobenzene.
c) methylbenzene.
d) ethylbenzene.
e) methoxybenzene.
Difficulty: Easy
Learning Objective: Draw and name aromatic compounds using the IUPAC system.
Section Reference: 10.2 Aromatic Compounds
21. Which compound below is a secondary alcohol?
a)
b)
c)
d) CH3CH2CH2CH2OH
e) CH3CH2CH2OCH3
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
22. Which compound is a secondary amine?
a) CH3CH2CH2NH2
b)
c)
d)
e)
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
23. Which compound is an aldehyde?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
24. Which compound is a ketone?
a)
b)
c)
d)
e)
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
25. Which compound is an ester?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
26. The compound shown below is a synthetic estrogen. It is marketed as an oral contraceptive under the name Enovid.
In addition to an alkane (actually cycloalkane) skeleton, the Enovid molecule also contains the following functional groups:
a) ether, alcohol, alkyne
b) aldehyde, alkene, alkyne, alcohol
c) alcohol, carboxylic acid, alkene, alkyne
d) ketone, alkene, alcohol, alkyne
e) amine, alkene, ether, alkyne
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
27. Which is a 3o alkyl halide?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
28. Which is the 3o amine?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
29. Which functional group is NOT contained in prostaglandin E1?
a) ketone
b) 2o alcohol
c) 3o alcohol
d) carboxylic acid
e) alkene
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
30. The compound below is an adrenocortical hormone called cortisone. Which functional group is not present in cortisone?
a) 1o alcohol
b) 2o alcohol
c) 3o alcohol
d) ketone
e) alkene
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
31. The compound shown below is a substance called Capsaicin, found in varying concentrations in several varieties of hot peppers, and responsible for their respective degrees of “heat”. Which functional groups are present in the molecule of capsaicin?
a) alkene, ketone, amine, alcohol, ester
b) alkene, ketone, alcohol, ether
c) alkene, amine, phenol, ether
d) ether, phenol, alkene, amide
e) ester, phenol, alkene, amide
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
32. Drawn below is Atropine, found in Atropa belladonna, sometimes used in dilating pupils during an eye exam. Which of the following functional groups is NOT in atropine?
a) amine
b) ester
c) alcohol
d) benzene ring
e) ketone
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
33. The compound shown below is the male sex hormone, testosterone.
Which functional groups are present in the molecule?
a) alkene, ester, tertiary alcohol
b) alkene, ether, secondary alcohol
c) alkene, ketone, secondary alcohol
d) alkyne, ketone, secondary alcohol
e) alkene, ketone, tertiary alcohol
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
34. Which is a carboxylic acid?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
35. Which compound is a tertiary alcohol?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
36. Which compound is a primary amine with the formula C5H13N?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
37. Which compound can be classified as an ester as well as a ketone?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
38. Which compound(s) contain(s) tertiary carbon atom(s)?
a) I, II, III
b) I
c) II, III
d) I, IV
e) V
Difficulty: Medium
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
39. Which of the following is the enantiomer of the following substance?
a) I
b) II
c) III
d) It does not have a non-superposable enantiomer.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
40. Which of the following molecules is achiral?
a) I
b) II
c) III
d) IV
e) V
Difficulty: Hard
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
41. Hexane and 3-methylpentane are examples of
a) enantiomers.
b) sterioisomers.
c) diasteromers.
d) constitutional isomers.
e) non-superposable mirror images.
Difficulty: Easy
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
42. I and II are
a) constitutional isomers.
b) enantiomers.
c) non-superposable mirror images.
d) diastereomers.
e) non-isomeric.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
43. Pairs of enantiomers are
a) I, II and III, IV.
b) I, II.
c) III, IV.
d) IV, V.
e) I, IV.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
44. Chiral molecules are represented by
a) I, II, III, IV, and V.
b) I, II, III, and IV.
c) I and II.
d) III and IV.
e) IV.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
45. The molecules shown are
a) constitutional isomers.
b) enatiomers.
c) diasteromers.
d) identical.
e) stereoisomers.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
46. The molecules shown are
a) enantiomers.
b) diasteromers.
c) constitutional isomers.
d) two conformations of the same molecule.
e) not isomeric.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
47. The molecules shown are
a) constitutional isomers.
b) enantiomers.
c) diastereomers.
d) identical.
e) stereoisomers.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
48. The molecules below are
a) constitutional isomers.
b) enantiomers.
c) diastereomers.
d) identical.
e) stereoisomers.
Difficulty: Easy
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
49. The molecules shown are
a) enantiomers.
b) diastereomers.
c) constitutional isomers.
d) two different conformations of the same molecule.
e) not isomeric.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
50. Cis-trans isomers are
a) diastereomers.
b) enantiomers.
c) stereoisomers.
d) constitutional isomers.
e) more than one of these.
Difficulty: Easy
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
51. The molecules below are
a) constitutional isomers.
b) enantiomers.
c) diastereomers.
d) identical.
e) stereoisomers.
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
52. Which molecule (s) is(are) achiral?
a) I
b) II
c) III
d) I and II
e) I and III
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
53. Which molecule(s) is(are) achiral?
a) I
b) II
c) III
d) I and II
e) I and III
Difficulty: Medium
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
54. Which of the following represent (R)-2-butanol?
a) III and IV
b) I, III, IV and V
c) I, IV and V
d) I and III
e) I, II, IV and V
Difficulty: Hard
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
55. Which structure represents (S)-1-chloro-1-fluoroethane?
a) I
b) II
c) III
d) I and II
e) I and III
Difficulty: Hard
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
56. Which structure represents (R)-1-chloro-1-fluoroethane?
a) I
b) II
c) III
d) I and II
e) I and III
Difficulty: Hard
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
57. Which structure represents (S)-2-bromobutane?
a) I
b) II
c) III
d) I and II
e) I and III
Difficulty: Hard
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
58. 
is properly named
a) (3R,4S,5R)- 3,5-Dichloro-4-methylhexane.
b) (2S,3S,4S)- 2,4-Dichloro-3-methylhexane.
c) (2S,3R,4R)- 2,4-Dichloro-3-methylhexane.
d) (2S,3R,4S)-2,4-Dichloro-3-methylhexane.
e) (2S,3S,4R)- 2,4-Dichloro-3-methylhexane.
Difficulty: Hard
Learning Objective: Recognize, name, and draw stereoisomers and conformations.
Section Reference: 10.4 Stereochemistry
ESSAY QUESTIONS
59. Draw the line structure of 2-propanol.
Difficulty: Easy
Learning Objective: Draw and name compounds containing common functional groups.
Section Reference: 10.3 Functional Groups
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