Ch8 | Exam Questions – Alkenes And Alkynes Ii: Addition - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
Package title: Solomons Test Bank
Course Title: Solomons 13e
Chapter Number: 8
Question type: Multiple choice
1) The thermodynamic parameters at 298 K for the following reaction are given below.
Hº = -64.9 kJ mol-1
Sº = -131 J K-1 mol-1
Gº = -25.8 kJ mol-1
Which of the following statements is true of the reaction?
A) Both Hº and Sº favor product formation.
B) Neither Hº nor Sº favors product formation.
C) The entropy term is unfavorable but the formation of ethyl chloride is favored.
D) The entropy term is favorable but the formation of ethyl chloride is not favored.
E) The sign of Gº indicates that the reaction cannot occur as written.
Topic: General Information
Section: 8.1
Difficulty Level: Medium
2) The interaction of the bond of an alkene with an electrophile can initially result in the formation of a species termed a complex. Which of these cannot combine with an alkene to form a complex?
A) H+
B) NH3
C) Ag+
D) Hg2+
E) BF3
Topic: Reaction Products
Section: 8.1
Difficulty Level: Easy
3) Markovnikov addition of HI to 2-methyl-2-butene involves:
A) initial attack by an iodide ion.
B) initial attack by an iodine atom.
C) isomerization of 2-iodo-2-methylbutene.
D) formation of a carbocation at C-2.
E) formation of carbocation at C-3.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
4) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
5) What would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
6) Treating 1-methylcyclohexene with HCl would yield primarily which of these?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
7) How many compounds are possible from the addition of bromine to CH2=CHCH2CH3 (counting stereoisomers separately)?
A) One
B) Two
C) Three
D) Four
E) Five
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
8) (R)-3-Chloro-1-butene reacts with HCl by Markovnikov addition, and the products are separated by gas chromatography. How many total fractions would be obtained and how many would be optically active?
A) one optically active fraction only
B) one optically active fraction and one optically inactive
C) two optically active fractions
D) one optically active fraction and two optically inactive
E) two optically active fractions and one optically inactive
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
9) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
10) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
11) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
12) What product would you expect from addition of deuterium chloride to 2-cyclohexyl-4-methyl-2-pentene?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
13) Addition of hydrogen chloride to the following molecule would produce:
A) I and II
B) II and III
C) I and IV
D) V
E) All of these choices are equally likely to be formed.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
14) Consider the addition of HCl to 3-methyl-1-butene. The major product of the reaction would be:
A) 1-Chloro-2-methylbutane
B) 1-Chloro-3-methylbutane
C) 2-Chloro-2-methylbutane
D) 2-Chloro-3-methylbutane
E) 1-Chloropentane
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
15) What are possible products for the following reaction?
A) 
B) 
C) 
Topic: Reaction Products
Section: 8.2
Difficulty Level: Hard
16) What are the major product(s) formed by treating methylcyclopentene with HBr and MeO-OMe?
A) I
B) II
C) III
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
17) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 6.5, 8.2
Difficulty Level: Medium
18) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 7.6, 8.2
Difficulty Level: Medium
19) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Sequences
Section: 7.6, 8.2
Difficulty Level: Medium
20) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 7.6, 8.2
Difficulty Level: Medium
21) In general, when the addition of an unsymmetrical electrophilic reagent to an unsymmetrical alkene forms the product predicted by Markovnikov's rule, that occurs because:
A) the product is statistically favored.
B) steric hindrance favors its formation.
C) it is formed via the more/most stable carbocation.
D) it is the more/most stable product.
E) All of these choices are reasons.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
22) What is the chief product of the reaction of IBr with 2-methyl-2-pentene?
A) 2-bromo-3-iodo-2-methylpentane
B) 3-bromo-2-iodo-2-methylpentane
C) 1-bromo-2-iodo-2-methylpentane
D) 2-bromo-1-iodo-2-methylpentane
E) All of these choices.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
23) Treating 1-methylcyclohexene with H3O+ would yield primarily which of these?
A) I and V
B) II
C) III and V
D) IV
E) I, III, and V
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
24) What is the product(s) formed by treating 3,3-dimethylcyclopentene with H3O+ and heating?
A) I only
B) II and IV
C) I and III
D) IV and V
E) none of these choices
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
25) Which product would you expect from the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
26) What is the chief product of the acid-catalyzed hydration of 2,5-dimethyl-2-hexene?
A) 2,5-dimethyl-1-hexanol
B) 2,5-dimethyl-2-hexanol
C) 2,5-dimethyl-3-hexanol
D) 2,5-dimethyl-2,3-hexanediol
E) 2,5-dimethyl-3,4-hexanediol
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
27) Acid-catalyzed hydration of 2-methyl-1-butene would yield which of the following?
A) (CH3)2C(OH)CH2CH3
B) CH2OHCH(CH3)CH2CH3
C) (CH3)2CHCHOHCH3
D) (CH3)2CHCH2CH2OH
E) CH3CH2CH(CH3)CH2OH
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
28) When either cis- or trans-2-butene is treated with hydrogen chloride in ethanol, the product mixture that results includes:
A) CH3CH2CH2CH2Cl
B) CH3CH2CH2CH2OCH2CH3
C) CH3CH2CH(CH3)OCH2CH3
D) (CH3)3CCl
E) (CH3)2CHCH2OCH2CH3
Topic: Reaction Products
Section: 8.4
Difficulty Level: Medium
29) Which alkene would you expect to be most reactive toward acid-catalyzed hydration?
A) 1-pentene
B) trans-2-pentene
C) cis-2-pentene
D) 2-methyl-1-butene
E) All of these would be equally reactive.
Topic: General Information
Section: 8.4
Difficulty Level: Medium
30) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.5
Difficulty Level: Easy
31) What is the product(s) formed by treating 3,3-dimethyl-1-cyclopentene with Hg(OAc)2 in THF/water followed by treatment with NaBH4 in NaOH(aq)?
A) I only
B) II and IV
C) I and III
D) IV and V
E) none of these choices
Topic: Reaction Products
Section: 8.5
Difficulty Level: Easy
32) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.5
Difficulty Level: Easy
33) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.5
Difficulty Level: Medium
34) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.5
Difficulty Level: Medium
35) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.5
Difficulty Level: Medium
36) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 6.16, 8.5
Difficulty Level: Medium
37) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Sequences
Section: 7.15, 8.5
Difficulty Level: Medium
38) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 6.16, 8.6, 8.7, 8.8
Difficulty Level: Medium
39) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Sequences
Section: 7.15, 8.6, 8.7, 8.8
Difficulty Level: Medium
40) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 6.16, 8.7, 8.8, 8.9
Difficulty Level: Medium
41) Which of the following would be produced upon ozonolysis of camphene?
A) I, II, V
B) II, III
C) I, V
D) II, V
E) III, IV
Topic: Reaction Product
Section: 8.9
Difficulty Level: Medium
42) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 6.17, 8.7, 8.8, 8.9
Difficulty Level: Medium
43) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.6, 8.7, 8.8
Difficulty Level: Easy
44) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.6, 8.7, 8.8
Difficulty Level: Easy
45) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.6, 8.7, 8.8
Difficulty Level: Medium
46) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.6, 8.7, 8.8
Difficulty Level: Medium
47) What is the major product for the following reaction?
A) 
B) 
C) 
Topic: Reaction Products
Section: 8.6, 8.7, 8.8
Difficulty Level: Medium
48) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.6, 8.7, 8.8, 8.10
Difficulty Level: Medium
49) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.6, 8.7, 8.8, 8.10
Difficulty Level: Medium
50) How many of the products shown below are possible in the following reaction?
A) 1
B) 2
C) 4
D) All of them.
E) None of them.
Topic: Reaction Products
Section: 8.11
Difficulty Level: Medium
51) What would be the major product of the following reaction?
A) Equal amounts of I and II.
B) Equal amounts of II and III.
C) Equal amounts of III and IV.
D) I and II as major products, III and IV as minor products.
E) All of these choices in equal amounts.
Topic: Reaction Products
Section: 8.11
Difficulty Level: Medium
52) What would be the major product of the following reaction?
A) Equal amounts of I and II.
B) Equal amounts of II and III.
C) Equal amounts of III and IV.
D) I and II as major products, III and IV as minor products.
E) All of these choices in equal amounts.
Topic: Reaction Products
Section: 8.11
Difficulty Level: Medium
53) Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would:
A) be a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial.
B) be a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial.
C) be a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial.
D) be a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial.
E) be a pair of diastereomers and, in their most stable conformation, one would have the bromines equatorial and axial, and the other would have the bromines equatorial and equatorial.
Topic: Reaction Products
Section: 8.11
Difficulty Level: Medium
54) Compound X has the molecular formula C6H10. X decolorizes bromine in carbon tetrachloride. X also shows IR absorption at about 3300 cm-1. When treated with excess hydrogen and a nickel catalyst, X yields 2-methylpentane. The most likely structure for X is:
A) 
B) 
C) 
D) 
E) 
Topic: Structure Elucidation
Section: 2.16, 4.16, 8.11
Difficulty Level: Medium
55) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 7.10, 8.11
Difficulty Level: Medium
56) What reagent sequence might accomplish the following transformation?
A) 1) Br2, 2)excess KOH, 3)H3O+
B) 1) HBr, 2)excess KOH, 3) H3O+
C) 1) HBr, 2)excess NaNH2, 3) H3O+
D) 1) Br2, 2) excess NaNH2, 3) H3O+
E) none of these choices
Topic: Reaction Sequences
Section: 7.10, 8.11
Difficulty Level: Medium
57) A synthetic strategy for converting trans-2-butene into pure cis-2-butene would consist of which of the following?
A) Reaction with H2, Ni2B (P-2)
B) Reaction with i) Br2, CCl4; ii) 2 NaNH2, NH3(l); iii) Na, NH3 (l)
C) Reaction with H3O+, heat
D) Reaction with i) Br2, CCl4; ii) 2 NaNH2, NH3(l); iii) H2, Ni2B (P-2)
E) None of these will successfully effect the desired transformation.
Topic: Synthetic Strategy
Section: 7.10, 7.15, 8.11
Difficulty Level: Hard
58) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Sequences
Section: 7.15, 8.11
Difficulty Level: Medium
59) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Sequences
Section: 7.15, 8.11
Difficulty Level: Medium
60) Which reaction sequence would convert cis-2-butene to trans-2-butene?
A) Br2/CCl4; then 2 NaNH2; then H2/Ni2B(P-2)
B) Br2/CCl4; then 2 NaNH2; then Li/liq. NH3
C) H3O+, heat; then cold dilute KMnO4
D) HBr; then NaNH2; then H2, Pt
E) None of these choices.
Topic: Synthetic Strategy
Section: 7.10, 7.15, 8.11
Difficulty Level: Hard
61) The reaction of BrCl (bromine monochloride) with 1-methylcyclopentene will produce which of the following as the predominant product:
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.2, 8.11
Difficulty Level: Hard
62) Which of these compounds will react with cold concd. H2SO4, as well as Br2 in CCl4?
A) CH3CH2CH=CHCH3
B) CH3CH2CH2CH=CH2
C) CH3CH2CCCH3
D) (CH3)2CHCCH
E) All of these choices.
Topic: Structure Elucidation
Section: 8.4, 8.11
Difficulty Level: Easy
63) Which reaction is NOT stereospecific?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.12
Difficulty Level: Easy
64) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Easy
65) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Easy
66) What are the major product(s) formed by treating 1,2-dimethyl cyclopentene with Br2?
A) I,II
B) II, III
C) IV, V
D) I, III
E) None of these choices.
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Hard
67) Reaction of trans-2-hexene with a solution of Br2 in CCl4 produces:
A) I and II
B) II and V
C) III and IV
D) IV and V
E) V
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Medium
68) The reaction of Br2/CCl4 to cyclohexene would produce the compound(s) represented by structure(s):
A) I alone
B) II alone
C) II and III
D) III alone
E) I, II, and II
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Medium
69) Which of these is not a possible product when cyclopentene reacts with an aqueous solution of bromine?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.13
Difficulty Level: Easy
70) What would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.13
Difficulty Level: Easy
71) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.13
Difficulty Level: Easy
72) Which of these compounds belongs to the class of substances commonly known as "halohydrins"?
A) BrCH2CH2Cl
B) ClCH2CO2H
C) ICH2CH2OH
D) FCH2CH2NH2
E) HOCH2 COCl
Topic: General Information
Section: 8.13
Difficulty Level: Easy
73) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.13
Difficulty Level: Medium
74) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.13
Difficulty Level: Medium
75) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 6.5, 8.13
Difficulty Level: Hard
76) Which of these compounds is not formed when gaseous ethene is bubbled into an aqueous solution of bromine, sodium chloride and sodium nitrate?
A) BrCH2CH2Br
B) BrCH2CH2Cl
C) BrCH2CH2OH
D) ClCH2CH2OH
E) BrCH2CH2ONO2
Topic: Reaction Products
Section: 8.12, 8.13
Difficulty Level: Hard
77) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.14
Difficulty Level: Medium
78) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 7.15, 8.14
Difficulty Level: Hard
79) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Reaction Products
Section: 8.14
Difficulty Level: Easy
80) What product would result from the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.15
Difficulty Level: Easy
81) Which reagent(s) given below could be used to synthesize cis-1,2-cycloheptanediol from cycloheptene?
A) KMnO4, OH, 5oC
B) KMnO4, H3O+, 75oC
C) H2SO4, heat
D) All of these choices.
E) None of these choices.
Topic: Synthetic Strategy
Section: 8.15
Difficulty Level: Easy
82) Which set of reagents might be used to convert bromocyclohexane into cis-1,2-cyclohexanediol?
A) 1) Potassium tert-butoxide, 2) H3O+
B) 1) Potassium tert-butoxide, 2) OsO4, pyridine then NaHSO4(aq)
C) 1) KOH, 2) KMnO4, H+, heating
D) 1) NaOH, 2) H3O+, heating
E) none of these choices
Topic: Synthetic Strategy
Section: 8.15
Difficulty Level: Easy
83) Cyclohexene is treated with cold dilute alkaline KMnO4. Assuming syn addition, the spatial arrangement of the two hydroxyl groups in the product would be:
A) equatorial-axial
B) axial-axial
C) equatorial-equatorial
D) coplanar
E) Trans
Topic: Synthetic Strategy
Section: 8.15
Difficulty Level: Easy
84) Hydroxylation of cis-2-pentene with cold alkaline KMnO4 yields
A) Equal amounts of I and II.
B) Equal amounts of II and III.
C) Equal amounts of III and IV.
D) I and II as major products, III and IV as minor products.
E) All of these choices in equal amounts.
Topic: Reaction Products
Section: 8.15
Difficulty Level: Medium
85) 3,3-dimethylcyclohexene is subjected to reaction with cold, dilute KMnO4, to give 3,3-dimethyl-1,2-cyclohexanediol. In the most stable conformation of the product, the hydroxyl groups would be:
A) both axial
B) both equatorial
C) axial-equatorial
D) coplanar
E) None of these choices.
Topic: Reaction Products
Section: 8.15
Difficulty Level: Medium
86) An optically active compound, Y, with the molecular formula C7H12 gives a positive test with cold dilute KMnO4 and shows IR absorption at about 3300 cm-1. On catalytic hydrogenation, Y yields Z(C7H16) and Z is also optically active. Which is a possible structure for Y?
A) CH3CH2CH2CH2CH2CCH
B) (CH3)2CHCH2CH2CCH
C) CH3CH2CH(CH3)CH2CCH
D) CH3CH2CH(CH3)CCCH3
E) CH2=CHCH(CH3)CH2CH=CH2
Topic: Structure Elucidation
Section: 2.16, 4.16, 8.15
Difficulty Level: Medium
87) An optically active compound, A, with the molecular formula C7H12 reacts with cold dilute KMnO4 and gives IR absorption at about 3300 cm-1. On catalytic hydrogenation, A is converted to B (C7H16) and B is also optically active. Which is a possible structure for A?
A) I
B) II
C) III
D) IV
E) V
Topic: Structure Elucidation
Section: 2.16, 4.16, 7.13, 8.15
Difficulty Level: Hard
88) Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 5.12, 8.15
Difficulty Level: Easy
89) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 6.16, 8.15
Difficulty Level: Medium
90) What is the final product of the following synthesis?
A) I
B) II
C) III
D) IV
E) An equimolar mixture of III and IV.
Topic: Reaction Products
Section: 7.15, 8.15
Difficulty Level: Medium
91) Which of the following reagents might serve as the basis for a simple chemical test that would distinguish between pure 1-pentene and pure pentane?
A) Bromine in carbon tetrachloride
B) Dilute aqueous potassium permanganate
C) Concentrated sulfuric acid
D) All of these choices.
E) Bromine in carbon tetrachloride and dilute aqueous potassium permanganate only
Topic: Structure Elucidation
Section: 8.4, 8.11, 8.15
Difficulty Level: Easy
92) Which reagent or test could be used to distinguish between 2-methyl-2-pentene and 2-methylpentane?
A) Br2/CCl4
B) KMnO4, OH
C) Concd. H2SO4
D) All of these choices.
Topic: Structure Elucidation
Section: 8.4, 8.11, 8.15
Difficulty Level: Easy
93) Which reaction would yield a meso compound?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 5.12, 4.16, 8.11, 8.15
Difficulty Level: Medium
94) Which reaction would give a meso compound as the product?
A) Cyclopentene + Br2/CCl4
B) Cyclopentene + OsO4, then NaHSO3
C) Cyclopentene + H3O+
D) Cyclopentene + Cl2, H2O
Topic: Reaction Products
Section: 5.14, 8.5, 8.11, 8.15
Difficulty Level: Medium
95) A pair of enantiomers results from which of these reactions?
A) cyclopentene + cold, dil. KMnO4
B) trans-2-butene + Br2
C) 1-pentene + HCl
D) cis-2-butene + D2/Pt
E) cyclobutene + OsO4, then Na2SO3
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
96) Which of the following reactions would yield the final product as a racemic form?
A) Cyclohexene + Br2, H2O
B) Cyclohexene + cold, dilute KMnO4 and OH-
C) Cyclohexene + HCl
D) Cyclohexene + OsO4, then NaHSO3
E) Cyclohexene + D2/Pt
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
97) Which reaction is regioselective?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Easy
98) Which reaction would yield a racemic product?
A) Cyclopentene + D2/Pt
B) Cyclopentene + OsO4, then Na2SO3
C) Cyclopentene + Br2/H2O
D) Cyclopentene + cold, dilute KMnO4
E) Cyclopentene + dilute H2SO4
Topic: Reaction Products
Section: 8.2, 8.4, 8.11, 8.12, 8.13, 8.15
Difficulty Level: Medium
99) Which reaction of an alkene proceeds with anti addition?
A) Hydroboration/oxidation
B) Bromination
C) Oxidation with cold KMnO4
D) Hydrogenation
E) Oxymercuration-demercuration
Topic: Reaction Products
Section: 8.5, 8.6, 8.6, 8.8, 8.11, 8.12, 8.15
Difficulty Level: Medium
100) What is the major product of the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.15
Difficulty Level: Medium
101) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 6.16, 8.15
Difficulty Level: Hard
102) The most resistant compound to the action of hot alkaline KMnO4 is:
A) Pentane
B) 1-Pentene
C) 2-Pentene
D) 2-Pentyne
E) Cyclopentene
Topic: General Information
Section: 8.16
Difficulty Level: Easy
103) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Products
Section: 8.16
Difficulty Level: Medium
104) Which alkene would yield only CH3CH2COOH on oxidation with hot alkaline potassium permanganate (followed by acid work-up)?
A) (E)-2-hexene
B) (Z)-2-hexene
C) 2-methyl-2-pentene
D) (E)-3-hexene
E) (E)-4-methyl-2-pentene
Topic: Structure Elucidation
Section: 8.16
Difficulty Level: Medium
105) Determine a possible structure for an alkene, X, formula C9H14, on the basis of the following information: X adds one mole of hydrogen on catalytic hydrogenation. On treatment with hot basic KMnO4 followed by acidification, X yields the following dicarboxylic acid.
A possible structure for X might be:
A) I
B) II
C) III
D) IV
E) V
Topic: Structure Elucidation
Section: 4.16, 8.16
Difficulty Level: Hard
106) Which of the following reactions of cyclobutene would yield a meso product?
A) reaction with H3O+, H2O
B) reaction with Br2, CCl4
C) reaction with Cl2, CCl4
D) reaction with D2, Pt
E) reaction with hot, alkaline KMnO4, followed by acid workup
Topic: Synthetic Strategy
Section: 8.4, 8.11, 8.12, 8.16
Difficulty Level: Hard
107) What reagents might be used to convert cis-2-butene into trans-2-butene?
A) 1)Br2; 2)NaOEt, EtOH
B) 1)HBr; 2)NaOEt, EtOH
C) 1) H3O+, heat; 2) NaOEt, EtOH
D) 1) H2, Pd/C, 2) NaOEt, EtOH
E) None of these choices
Topic: Synthetic Strategy
Section: 8.4, 8.11, 8.12, 8.16
Difficulty Level: Medium
108) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.16
Difficulty Level: Easy
109) An unknown compound X was subjected to ozonolysis and was found to the following products. Determine which of the following compounds listed below could be the unknown X?
A) I
B) II
C) III
D) IV
E) V
Topic: Structure Elucidation
Section: 4.16, 8.16
Difficulty Level: Hard
110) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.16
Difficulty Level: Easy
111) Which substance would undergo the following reaction?
A) 4-Hexen-1-yne
R
B) 3-methyl-1-hexene
C) (E)-2-hexene
D) (Z)-2-hexene
E) 4-methyl-1-pentene
Topic: Reaction Products
Section: 8.16
Difficulty Level: Medium
112) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
Topic: Structure Elucidation
Section: 8.16
Difficulty Level: Medium
113) Ozonolysis of compound Z yields the products shown below. What is the structure of Z?
A) I
B) II
C) III
D) IV
E) V
Topic: Structure Elucidation
Section: 8.16
Difficulty Level: Medium
114) An alkene with the molecular formula C10H18 is treated with ozone and then with zinc and acetic acid. The only product isolated from these reactions is:
What is the structure of the alkene?
A) I
B) II
C) III
D) IV
E) V
Topic: Structure Elucidation
Section: 8.16
Difficulty Level: Medium
115) Consider the ozonolysis products obtained from all the unbranched and unsymmetrical isomers of heptene. The reaction product in each case would consist of:
A) a single aldehyde.
B) an aldehyde and a ketone.
C) two different ketones.
D) two different aldehydes.
E) a single ketone.
Topic: General Information
Section: 8.16
Difficulty Level: Medium
116) An alkene adds hydrogen in the presence of a catalyst to give 3,4-dimethylhexane. Ozonolysis of the alkene followed by treatment with zinc and acetic acid gives a single organic product. The structure of the alkene is:
A) 
B) 
C) 
D) 
E) 
Topic: Structure Elucidation
Section: 4.16, 8.16
Difficulty Level: Medium
117) Compound C has the molecular formula C7H12. On catalytic hydrogenation, 1 mol of C absorbs 1 mol of hydrogen and yields a compound with the molecular formula C7H14. On ozonolysis and subsequent treatment with zinc and acetic acid, C yields only:
The structure of C is:
A) I
B) II
C) III
D) IV
E) V
Topic: Structure Elucidation
Section: 4.16, 8.16
Difficulty Level: Medium
118) An alkene with the molecular formula C8H16 undergoes ozonolysis to yield a mixture of (CH3)2C=O and (CH3)3CCHO. The alkene is:
A) 2,2-Dimethyl-2-hexene
B) 2,3-Dimethyl-2-hexene
C) 2,4-Dimethyl-2-hexene
D) 2,4,4-Trimethyl-2-pentene
E) More than one of these choices is a possible answer.
Topic: Structure Elucidation
Section: 4.16, 8.16
Difficulty Level: Medium
119) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Reaction Sequences
Section: 6.16, 8.16
Difficulty Level: Medium
120) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 7.6, 8.16
Difficulty Level: Medium
121) One mole of an optically active compound, X, with the molecular formula C6H8 reacts with three moles of hydrogen in the presence of a catalyst to yield an optically inactive product that cannot be resolved. X also exhibits IR absorption at approximately 3300 cm-1. Which is a possible structure for X?
A) (E)-4-hexen-1-yne
B) (Z)-4-hexen-1-yne
C) (E)-2-hexen-4-yne
D) 2-methyl-1-penten-3-yne
E) 3-methyl-1-penten-4-yne
Topic: Structure Elucidation
Section: 2.16, 4.16, 7.13, 8.16
Difficulty Level: Hard
122) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
Topic: Reaction Sequences
Section: 7.15, 8.16
Difficulty Level: Medium
123) Select the structure of the major product formed in the following reaction.
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.17
Difficulty Level: Easy
124) Select the structure of the major product formed in the following reaction.
A) I
B) II
C) III
D) IV
E) V
Topic: Reaction Products
Section: 8.18
Difficulty Level: Easy
125) Addition of 2 mol of HCl to 1-butyne would yield:
A) CH3CH2CH2CHCl2
B) CH3CH2CCl2CH3
C) CH3CH2CHClCH2Cl
D) CH3CH2CH=CHCl
E) CH3CHClCHClCH3
Topic: Reaction Products
Section: 8.18
Difficulty Level: Easy
126) Addition of excess HCl to 2-methyl-3-heptyne would produce:
2-methyl-3,3-dichloroheptane 2-methyl-2,3-dichloroheptane
I II
2-methyl-4,4-dichloroheptane 2-methyl-3,4-dichloroheptane
III IV
2-methyl-3-chloroheptene
V
A) I and II
B) I and III
C) II and IV
D) V
E) All of these choices.
Topic: Reaction Products
Section: 8.18
Difficulty Level: Medium
127) The conversion of ethylene to vinyl bromide can be accomplished by use of these reagents in the order indicated.
A) (1) HBr; (2) NaOC2H5
B) (1) Br2; (2) NaOC2H5
C) (1) Br2; (2) H2O
D) (1) NaNH2; (2) HBr
E) (1) HBr; (2) H2SO4
Topic: Synthetic Strategy
Section: 7.10, 8.18
Difficulty Level: Medium
128) What is the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Sequences
Section: 8.2, 8.18
Difficulty Level: Medium
129) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Reaction Products
Section: 8.19
Difficulty Level: Easy
130) An unknown compound, A, has the molecular formula C7H12. On oxidation with hot aqueous potassium permanganate, A yields CH3CH2COOH and (CH3)2CHCOOH. Which of the following structures best represents A?
A) 
B) 
C) 
D) 
E) 
Topic: Structure Elucidation
Section: 8.19
Difficulty Level: Medium
131) What compound would yield an equimolar mixture of CH3CH2CH2CHO and CH3CHO upon treatment with O3, followed by Zn/HOAc?
A) 1-Hexene
B) cis-2-Hexene
C) trans-2-Hexene
Topic: Structure Elucidation
Section: 8.16, 8.19
Difficulty Level: Medium
132) Which of the following could be used as the basis for a simple test that would distinguish between 1-pentyne and pentane?
A) IR examination
B) Br2/CCl4
C) KMnO4/H2O
D) All of these choices.
Topic: Structure Elucidation
Section: 2.16, 8.17, 8.19
Difficulty Level: Easy
133) Which reagent or test could be used to distinguish between 3-pentyne and 1-pentyne?
A) Br2/CCl4
B) IR examination
C) Concd. H2SO4
D) KMnO4,OH-
E) None of these choices.
Topic: Structure Elucidation
Section: 2.16, 8.4, 8.17, 8.19
Difficulty Level: Easy
134) A reagent or test that could be used to distinguish between 1-pentene and 1-pentyne would be:
A) Bromine in carbon tetrachloride
B) Dilute aqueous potassium permanganate
C) Chlorine in carbon tetrachloride
D) H2SO4
E) IR examination
Topic: Structure Elucidation
Section: 2.16, 8.4, 8.11, 8.15, 8.17, 8.19
Difficulty Level: Easy
135) Which of the following could be used to distinguish between 1-octyne and 3-octyne?
A) Treatment with 2 mol of HX
B) Addition of water
C) Reaction with KMnO4
D) Decolorization of bromine in CCl4
E) IR examination
Topic: Structure Elucidation
Section: 2.16, 8.17, 8.18, 8.19
Difficulty Level: Easy
136) 2-Pentyne will not react with:
A) H2, Pt
B) Br2
C) NH3
D) H2SO4
E) KMnO4/H2O
Topic: General Information
Section: 7.13, 8.17, 8.18, 8.19
Difficulty Level: Medium
Question type: True/False
137) The reason why anti-Markovnikov addition is seen in the hydration of alkenes using hydroboration-oxidation conditions is due to steric interactions with the boron group attaching to the less substituted carbon more easily.
Topic: General Information
Section: 8.2
Difficulty Level: Medium
138) The yields for an acid catalyzed hydration of an alkene can be increased by using dilute acid as this will help drive the equilibrium to products.
Topic: Hydration of an Alkene
Section: 8.4
Difficulty Level: Easy
139) Due to the formation of a mercurinium ion in hydration of an alkene using oxymercuration-demercuration, we see overall anti-product form making this reaction stereospecific.
Topic: Oxymercuration-Demercuration
Section: 8.5
Difficulty Level: Hard
140) In halohydrin formation the reason why the halohydrin is the major product is because the solvent is more reactive that the bromide nucleophile.
Topic: Halohydrins
Section: 8.13
Difficulty Level: Easy
141) Potassium permanganate is usually a preferred reagent for oxidative cleavage to form aldehyde, as it is a much milder and less toxic reagent than osmium tetroxide.
Topic: Oxidation of Alkenes
Section: 8.15
Difficulty Level: Medium
Question type: fill-in-the-blank
bonds are quite susceptible to reaction with electron-seeking reagents, also referred to as ___.
Topic: General Information
Section: 8.1
Difficulty Level: Easy
143) The rule that correctly predicts the regiochemistry of most ionic additions to alkenes is called ___.
Topic: General Information
Section: 8.2
Difficulty Level: Easy
144) The introduction of a small amount of a peroxide to a hydrogen halide addition of an alkene will result in a(n) ___ addition where the hydrogen in the addition appears adds to the carbon with the ___ number of hydrogens.
Topic: General Information
Section: 8.2
Difficulty Level: Easy
Question type: Essay
145) Provide a mechanistic explanation for the following observation: The same major product is obtained when 2-ethyl-1-hexene and 3-methyl-2-heptene are allowed to react with HCl.
Both alkenes are unsymmetrically substituted: the major product is a consequence of regioselective addition to the double bond. Upon reaction with HCl, electrophilic addition of a proton results in the formation of the most stable intermediate carbocation, which then reacts with Cl, to give the observed product.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
146) Give a mechanistic explanation for the formation of the following product in significant yield. What other product(s) might also be obtained? Explain clearly.
The regioselective addition of a proton first generates a secondary carbocation, which can undergo rearrangement to a more stable 3o carbocation by two alternate pathways. One pathway results in ring expansion to a more stable 5-membered ring. This pathway is thus more likely, which would then lead to the observed product. The other pathway is less likely, since ring strain is not relieved; however, this could lead to a minor product, as shown above.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
147) Propose a mechanism for the following transformation accounting for the stereochemistry in the final product:
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
Question type: fill-in-the-blank
148) When a reaction that could potentially yield two or more constitutional isomers instead produces only one as the major product, the reaction is said to be ___.
Topic: General Information
Section: 8.2
Difficulty Level: Easy
149) Hydroboration-oxidation is a reaction with ___ stereochemistry and ___ regiochemistry.
Topic: General Information
Section: 8.6, 8.7, 8.8
Difficulty Level: Medium
Question type: Essay
150) Predict the final product(s) obtained when (2R,3R)-2-bromo-3-methylpentane is subjected to the following sequence of reactions, briefly explaining your rationale. Provide regiochemical and stereochemical details as relevant.
NaOC2H5/C2H5OH, heat
BH3, THF
H2O2, OH
Heating with sodium ethoxide results in E2 elimination; the anti- elimination leads to the formation of E-3-methyl-2-hexene as the major product. Subsequent hydroboration oxidation is regioselective (anti-Markovnikov) and stereospecific (syn), resulting in the formation of racemic (2S,3R & 2R,3S) 3-methyl-2-pentanol. The other diastereomer pair (2S,3S & 2R,3R) is not expected to be obtained.
Topic: Reaction Sequence
Section: 6.16, 8.6, 8.7, 8.8
Difficulty Level: Medium
151) Even when one or more stereogenic centers are produced as the result of an addition reaction to an alkene, the product is always formed as a racemic mixture. Why is that?
Topic: General Information
Section: 8.3, 8.5, 8.7, 8.11
Difficulty Level: Medium
Question type: fill-in-the-blank
152) When a particular stereoisomer reacts in such a way that it gives a particular stereoisomer as a product, even if more than one stereoisomer is theoretically possible, the reaction is said to be ___.
Topic: General Information
Section: 8.12
Difficulty Level: Easy
153) A reaction in which the reactant is not necessarily chiral but still produces primarily one stereoisomeric form of the product (or a specific subset of the possible stereoisomers) is referred to as a ___ reaction.
Topic: General Information
Section: 8.12
Difficulty Level: Easy
Question type: Essay
154) Draw Fischer projection formulas of the major product of the reaction between E-2-methyl-3-hexene and aqueous Br2.
The reaction takes place with anti stereospecificity. Since the alkene is symmetrically substituted, Markovnikov rule is not applicable, and the reaction is not regioselective. The product mixture would therefore consist of 2 pairs of enantiomers, that are constitutional isomers of each other.
Topic: Reaction Products
Section: 8.13
Difficulty Level: Medium
155) Predict the major product(s) of the following reaction, giving regiochemical and/or stereochemical details as relevant.
The reaction takes place with Markovnikov regioselectivity and anti stereospecificity, giving a racemic mixture of the halohydrin as the major product.
Topic: Reaction Products
Section: 8.2, 8.13
Difficulty Level: Medium
156) Carbenes are frequently produced by α-elimination reactions. These are reactions in which the proton being lost and the leaving group are ___.
Topic: General Information
Section: 8.14
Difficulty Level: Easy
157) Neutral divalent carbon compounds are called ___.
Topic: General Information
Section: 8.14
Difficulty Level: Medium
158) Predict the structure of product obtained when cis-2-hexene is allowed to react with Zn/CH2I2.
The Zn/CH2I2 produces a carbene which reacts with the alkene to give the corresponding cyclopropane derivative. The reaction proceeds with retention of alkene stereochemistry, resulting in a racemic mixture of the two cis enantiomers.
Topic: Reaction Products
Section: 8.14
Difficulty Level: Easy
159) Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-2-methyl-3-hexene and cold, alkaline KMnO4.
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol product.
Topic: Reaction Products
Section: 8.15
Difficulty Level: Medium
160) Draw Fischer projection formula(s) of the major product(s) of the reaction between Z-3-methyl-3-hexene and cold, alkaline KMnO4.
The reaction takes place with syn stereospecificity, giving a racemic mixture of the diol product.
Topic: Reaction Products
Section: 8.15
Difficulty Level: Medium
161) Predict the product(s) of the oxidation of 2,3,4-trimethyl-1,5-heptadiene with hot, alkaline KMnO4.
Topic: Reaction Products
Section: 8.16
Difficulty Level: Medium
162) Deduce the structure of an unknown compound A, C8H14, from the following data. Briefly, but clearly explain your rationale. A decolorizes Br2/CCl4, and upon reaction with excess H2/Ni, affords 1-ethyl-2-methylcyclopentane. When A is subjected to ozonolysis, the following product is obtained.
Topic: Structure Elucidation
Section: 4.16, 8.11, 8.16
Difficulty Level: Hard
163) The “decolorization” of molecular bromine is often used as a functional group test to detect the presence of ___.
Topic: General Information
Section: 8.11, 8.17
Difficulty Level: Easy
164) Predict the oxidative product(s) of 2-methyl-6-octyn-2-ene after undergoing ozonolysis.
Topic: Oxidative Methods
Section: 4.16, 8.19
Difficulty Level: Medium
165) Devise a retrosynthetic strategy to make the epoxide shown below starting from cyclohexanol and show the forward reaction with the necessary reagents and significant intermediates.
Topic: Retrosynthetic Analysis
Section: 6.5, 8.13, 8.20
Difficulty Level: Hard
166) How many compounds are possible from the addition of hydrobromic acid to CH2=CHCH2CH3 (counting stereoisomers separately)?
A) One
B) Two
C) Three
D) Four
E) Five
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
167) How many compounds are possible from the addition of hydrobromic acid to CH2=CHCH3 (counting stereoisomers separately)?
A) One
B) Two
C) Three
D) Four
E) Five
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
168) How many compounds are possible from the addition of bromine to CH2=CHCH3 (counting stereoisomers separately)?
A) One
B) Two
C) Three
D) Four
E) Five
Topic: Reaction Products
Section: 8.2
Difficulty Level: Easy
169) Consider the addition of HCl to 2-methyl-1-butene. The major product of the reaction would be:
A) 1-Chloro-2-methylbutane
B) 1-Chloro-3-methylbutane
C) 2-Chloro-2-methylbutane
D) 2-Chloro-3-methylbutane
E) 1-Chloropentane
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
170) What is the chief product of the reaction of IBr with 3-methyl-2-pentene?
A) 2-bromo-3-iodo-3-methylpentane
B) 3-bromo-2-iodo-3-methylpentane
C) 1-bromo-2-iodo-3-methylpentane
D) 2-bromo-1-iodo-3-methylpentane
E) All of these choices.
Topic: Reaction Products
Section: 8.2
Difficulty Level: Medium
171) What is the chief product of the acid-catalyzed hydration of 3,5-dimethyl-2-hexene?
A) 3,5-dimethyl-1-hexanol
B) 3,5-dimethyl-2-hexanol
C) 3,5-dimethyl-3-hexanol
D) 3,5-dimethyl-2,3-hexanediol
E) 3,5-dimethyl-3,4-hexanediol
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
172) What is the chief product of the acid-catalyzed hydration of 2,4-dimethyl-2-hexene?
A) 2,4-dimethyl-1-hexanol
B) 2,4-dimethyl-2-hexanol
C) 2,4-dimethyl-3-hexanol
D) 2,4-dimethyl-2,3-hexanediol
E) 2,4-dimethyl-3,4-hexanediol
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
173) What is the chief product of the acid-catalyzed hydration of 2,5-dimethyl-1-hexene?
A) 2,5-dimethyl-1-hexanol
B) 2,5-dimethyl-2-hexanol
C) 2,5-dimethyl-3-hexanol
D) 2,5-dimethyl-2,3-hexanediol
E) 2,5-dimethyl-3,4-hexanediol
Topic: Reaction Products
Section: 8.4
Difficulty Level: Easy
174) Which alkene would you expect to be least reactive toward acid-catalyzed hydration?
A) 1-pentene
B) trans-2-pentene
C) cis-2-pentene
D) 2-methyl-1-butene
E) All of these would be equally reactive.
Topic: General Information
Section: 8.4
Difficulty Level: Medium
175) A synthetic strategy for converting cis-2-butene into pure trans-2-butene would consist of which of the following?
A) Reaction with H2, Ni2B (P-2)
B) Reaction with i) Br2, CCl4; ii) 2 NaNH2, NH3(l); iii) Na, NH3 (l)
C) Reaction with H3O+, heat
D) Reaction with i) Br2, CCl4; ii) 2 NaNH2, NH3(l); iii) H2, Ni2B (P-2)
E) None of these will successfully effect the desired transformation.
Topic: Synthetic Strategy
Section: 7.10, 7.15, 8.11
Difficulty Level: Hard
176) Which reaction sequence would convert trans-2-butene to cis-2-butene?
A) Br2/CCl4; then 2 NaNH2; then H2/Ni2B(P-2)
B) Br2/CCl4; then 2 NaNH2; then Li/liq. NH3
C) H3O+, heat; then cold dilute KMnO4
D) HBr; then NaNH2; then H2, Pt
E) None of these choices.
Topic: Synthetic Strategy
Section: 7.10, 7.15, 8.11
Difficulty Level: Hard
177) Which of these compounds will react with H2/Ni2B(P-2)?
A) CH3CH2CH=CHCH3
B) CH3CH2CH2CH=CH2
C) CH3CH2CCCH3
D) (CH3)2CHCCH
E) Both C and D.
Topic: Structure Elucidation
Section: 8.4, 8.11
Difficulty Level: Easy
178) What are the major product(s) formed by treating 1,2-dimethyl cyclopentene with HBr?
A) I,II
B) II, III
C) IV, V
D) I, III
E) None of these choices.
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Hard
179) Reaction of cis-2-hexene with a solution of Br2 in CCl4 produces:
A) I and II
B) II and V
C) III and IV
D) IV and V
E) V
Topic: Reaction Products
Section: 8.11, 8.12
Difficulty Level: Medium
180) Hydroxylation of trans-2-pentene with cold alkaline KMnO4 yields
A) Equal amounts of I and II.
B) Equal amounts of II and III.
C) Equal amounts of III and IV.
D) I and II as major products, III and IV as minor products.
E) All of these choices in equal amounts.
Topic: Reaction Products
Section: 8.15
Difficulty Level: Medium
181) What is the major product of the following reaction?
A) (2R,3R)-2,3-dibromobutane + enantiomer
B) butane
C) (2R,3S)-2,3-butanediol
D) (2R,3R)-2,3-butanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 5.12, 4.16, 8.11, 8.15
Difficulty Level: Medium
182) What is the major product of the following reaction?
A) (2R,3R)-2,3-dibromobutane + enantiomer
B) butane
C) (2R,3S)-2,3-butanediol
D) (2R,3R)-2,3-butanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 5.12, 4.16, 8.11, 8.15
Difficulty Level: Medium
183) What is the major product of the following reaction?
A) (2R,3R)-2,3-dibromobutane + enantiomer
B) butane
C) (2R,3S)-2,3-butanediol
D) (2R,3R)-2,3-butanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 5.12, 4.16, 8.11, 8.15
Difficulty Level: Medium
184) What is the major product of the following reaction?
A) (2R,3R)-2,3-dibromobutane + enantiomer
B) butane
C) (2R,3S)-2,3-butanediol
D) (2R,3R)-2,3-butanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 5.12, 4.16, 8.11, 8.15
Difficulty Level: Medium
185) What is the major product when cyclopentene is reacted with Br2 in CCl4?
A) trans-1,2-dibromocyclopentane
B) cis-1,2-cyclopentanediol
C) cyclopentanol
D) 2-chlorocyclopentanol
E) None of these choices.
Topic: Reaction Products
Section: 5.14, 8.5, 8.11, 8.15
Difficulty Level: Medium
186) What is the major product when cyclopentene is reacted with OsO4, then NaHSO3?
A) trans-1,2-dibromocyclopentane
B) cis-1,2-cyclopentanediol
C) cyclopentanol
D) 2-chlorocyclopentanol
E) None of these choices.
Topic: Reaction Products
Section: 5.14, 8.5, 8.11, 8.15
Difficulty Level: Medium
187) What is the major product when cyclopentene is reacted with H3O+?
A) trans-1,2-dibromocyclopentane
B) cis-1,2-cyclopentanediol
C) cyclopentanol
D) 2-chlorocyclopentanol
E) None of these choices.
Topic: Reaction Products
Section: 5.14, 8.5, 8.11, 8.15
Difficulty Level: Medium
188) What is the major product when cyclopentene is reacted with Cl2 in H2O?
A) trans-1,2-dibromocyclopentane
B) cis-1,2-cyclopentanediol
C) cyclopentanol
D) 2-chlorocyclopentanol
E) None of these choices.
Topic: Reaction Products
Section: 5.14, 8.5, 8.11, 8.15
Difficulty Level: Medium
189) What is the major product when cyclopentane is reacted with cold, dil. KMnO4?
A) cis-1,2-cylopentanediol
B) (2R,3S)-2,3-dibromobutane
C) 2-chloropentane
D) cis-1,2-cyclobutanediol
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
190) What is the major product when trans-2-butene is reacted with Br2?
A) cis-1,2-cylopentanediol
B) (2R,3S)-2,3-dibromobutane
C) 2-chloropentane
D) cis-1,2-cyclobutanediol
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
191) What is the major product when 1-pentene is reacted with HCl?
A) cis-1,2-cylopentanediol
B) (2R,3S)-2,3-dibromobutane
C) 2-chloropentane
D) cis-1,2-cyclobutanediol
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
192) What is the major product when cyclobutene is reacted with OsO4, then Na2SO3?
A) cis-1,2-cylopentanediol
B) (2R,3S)-2,3-dibromobutane
C) 2-chloropentane
D) cis-1,2-cyclobutanediol
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
193) What is the major product when cyclohexene is reacted with Br2 in H2O?
A) (1R,2R)-2-bromocyclohexanol + enantiomer
B) (1R,2S)-1,2-cyclohexanediol
C) chlorocyclohexane
D) (1R,2R)-1,2-cyclohexanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
194) What is the major product when cyclohexene is reacted with cold, dilute KMnO4 and OH-?
A) (1R,2R)-2-bromocyclohexanol + enantiomer
B) (1R,2S)-1,2-cyclohexanediol
C) chlorocyclohexane
D) (1R,2R)-1,2-cyclohexanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
195) What is the major product when cyclohexene is reacted with HCl?
A) (1R,2R)-2-bromocyclohexanol + enantiomer
B) (1R,2S)-1,2-cyclohexanediol
C) chlorocyclohexane
D) (1R,2R)-1,2-cyclohexanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
196) What is the major product when cyclohexene is reacted with OsO4, then NaHSO3?
A) (1R,2R)-2-bromocyclohexanol + enantiomer
B) (1R,2S)-1,2-cyclohexanediol
C) chlorocyclohexane
D) (1R,2R)-1,2-cyclohexanediol + enantiomer
E) None of these choices.
Topic: Reaction Products
Section: 8.2, 8.11, 8.12, 8.15
Difficulty Level: Medium
197) Addition of 1 mol of Cl2 to 1-butyne would yield:
A) CH3CH2CH2CHCl2
B) CH3CH2CCl2CH3
C) CH3CH2CHClCH2Cl
D) CH3CH2CH=CHCl
E) CH3CHClCHClCH3
Topic: Reaction Products
Section: 8.18
Difficulty Level: Easy