Ch7 Test Questions & Answers Alkenes & Alkynes Reactions - Organic Chemistry 13e | Test Bank by Solomons by Graham Solomons. DOCX document preview.
Package Title: Solomons Test Bank
Course Title: Solomons 13e
Chapter Number: 7
Question type: Multiple Choice
1) The correct IUPAC name for the following compound is:
A) 2-Bromo-4-methylenehexane
B) 2-(2-Bromopropyl)-1-butene
C) 4-Bromo-2-ethyl-1-pentene
D) 2-Bromo-4-ethyl-1-pentene
E) 2-Bromo-4-ethyl-4-pentene
Topic: Nomenclature
Section: 4.3, 4.5, 7.2
Difficulty Level: Easy
2) Name the following compound:
A) (cis)-3-methoxyhex-3-ene
B) (Z)-4-methoxyhex-4-ene
C) (Z)-3-methoxyhex-3-ene
D) (E)-3-methoxyhex-3-ene
E) 3-methoxyhex-3-ene
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
3) Name the following compound:
A) (E)-4-phenyl-4-methylbut-3-en-1-ol
B) (E)-4-phenylpent-3-en-1-ol
C) (Z)-4-phenylpent-3-en-1-ol
D) (Z)-4-phenyl-4-methylbut-3-en-1-ol
E) (E)-4-benzylpent-3-en-1-ol
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
4) Which structure represents (Z)-4-bromohexa-1,3-diene?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
5) Which structure represents (E)-1-bromo-2-methylhex-2-ene?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
6) Which structure represents (Z)-1,4-dichlorohex-3-en-1-yne?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 7.2
Difficulty Level: Medium
7) A correct IUPAC name for the following compound is:
A) 3,3,5-trimethyl-2-hexene
B) 3-isobutyl-3-isopropyl-2-propene
C) 3-isobutyl-4-methyl-2-pentene
D) 3-(1-methylethyl)-5-methyl-2-hexene
E) None of these choices.
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
8) The correct IUPAC name for the following compound is:
A) 4,5-Dimethyl-3-propyl-2-hexene
B) 4,5-Dimethyl-3-propyl-1-hexene
C) 3-(2,3-Dimethylpropyl)-1-hexene
D) 2,3-Dimethyl-4-isopropyl-5-hexene
E) 2,3-Dimethyl-4-propyl-5-hexene
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
9) Select the structure of 4–ethyl-2,3-dimethyl-2-heptene.
A) 
B) 
C) 
D) 
E) 
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Easy
10) The correct IUPAC name for the following compound is:
A) (E)-2-Bromo-3-chloro-5-methyl-2-hexene
B) (E)-2-Bromo-3-chloro-5-methyl-3-hexene
C) (Z)-2-Bromo-3-chloro-5-methyl-3-hexene
D) (Z)-2-Bromo-3-chloro-5-methyl-2-hexene
E) (E)-2-Methyl-5-bromo-4-chloro-4-hexene
Topic: Nomenclature
Section: 4.5, 7.2
Difficulty Level: Medium
11) Name the following compound:
A) (S,Z)-3-bromo-4-methylhex-2-ene
B) (S)-3-bromo-4-methylhex-2-ene
C) (S,Z)-4-bromo-3-methylhex-4-ene
D) (S,E)-3-bromo-4-methylhex-2-ene
E) (R,E)-3-bromo-4-methylhex-2-ene
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
12) Name the following compound:
A) (S,E)-2,4-dibromo-3-methylpent-2-ene
B) (R,Z)-2,4-dibromo-3-methylpent-2-ene
C) (R,E)-2,4-dibromo-3-methylpent-3-ene
D) (S,E)-2,4-dibromo-3-methylpent-3-ene
E) (R,E)-2,4-dibromo-3-methylpent-2-ene
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
13) Name the following compound:
A) (S,E)-3-methyl-5-phenyl-3-heptene
B) (S,E)-3-methyl-5-benzyl-3-heptene
B) (R,E)-3-methyl-5-phenyl-3-heptene
C) (S,Z)-3-methyl-5-phenyl-3-heptene
D) (R,Z)-3-methyl-5-phenyl-3-heptene
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Medium
14) Name the following compound:
A) (R,Z)-5-phenyloct-5-en-3-ol
B) (R,Z)-5-benzyloct-5-en-3-ol
C) (R,E)-5-phenyloct-5-en-3-ol
D) (R,E)-5-benzyloct-5-en-3-ol
E) (R,E)-5-benzyloct-3-en-6-ol
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
15) Which structure represents (R,Z)-5-methylhept-2-ene?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
16) Name the following compound:
A) (S,E)-3-chlorohex-4-en-1-yne
B) (R,E)-3-chlorohex-2-en-5-yne
C) (S,E)-3-chlorohex-2-en-5-yne
D) (R,E)-3-chlorohex-4-en-1-yne
E) (R,E)-3-chloropent-4-en-1-yne
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 4.6, 5.7, 7.2
Difficulty Level: Medium
17) Name the following compound:
A) (Z)-5-methylhex-4-en-2-yn-6-ol
B) (E)-5-methylhex-4-en-2-yn-6-ol
C) (E)-2-methylhex-2-en-4-yn-1-ol
D) (Z)-2-methylhex-2-en-4-yn-1-ol
E) (Z)-1-methylhex-2-en-3-yn-1-ol
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 4.6, 5.7, 7.2
Difficulty Level: Medium
18) Which molecule would have the lowest heat of hydrogenation?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy
19) Heats of hydrogenation data would be useful in comparing the relative stabilities of which of the following substances?
A) I, II, III
B) III, IV
C) I, II, V
D) Heats of hydrogenation data would not be a useful way to compare relative stabilities of any of the substances.
E) All of these substances could effectively be compared using heats of hydrogenation data.
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy
20) Which alkene would liberate the most heat per mole when subjected to catalytic hydrogenation?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Easy
21) Rank the following compounds from lowest to highest heat of hydrogenation:
A) I, II, III, IV
B) IV, III, II, I
C) II, III, IV, I
D) I, IV, III, II
E) none of these choices
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Medium
22) Concerning the relative stabilities of alkenes, which is a false statement?
A) Unless hydrogenation of the alkenes gives the same alkane, heats of hydrogenation cannot be used to measure their relative stabilities.
B) In general, the greater the number of alkyl groups attached to the carbon atoms of the double bond, the greater the stability of the alkene.
C) The greater the quantity of heat liberated on combustion or hydrogenation of an alkene, the greater its energy content.
D) trans-Cycloalkenes are always more stable than the cis-isomers.
E) Heats of combustion can be used to measure the relative stabilities of isomeric alkenes, even though their hydrogenation products are not identical.
Topic: Alkene Stability, Heats of Hydrogenation and Combustion
Section: 7.3
Difficulty Level: Medium
23) Which product (or products) would be formed in appreciable amount(s) when trans-1-bromo-2-methylcyclohexane undergoes dehydrohalogenation upon treatment with sodium ethoxide in ethanol?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Medium
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Medium
24) Your task is to convert 2-bromobutane to 1-butene in highest yield. Which reagents would you use?
A) KOH/H2O
B) KOH/CH3OH
C) CH3ONa/CH3OH
D) CH3CH2ONa/CH3CH2OH
E) (CH3)3COK/(CH3)3COH
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
25) What is the major product for the following reaction?
A) CH3CH2(CH3)C=CHCH3
B) CH3CH2(CH3)CHCH=CH2
C) CH3CH2(CH3)CHCH(OCH2CH3)CH3
D) None of these choices.
E) No reaction.
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
26) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
27) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
28) What is the major product for the following reaction?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
29) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
30) What is the major product for the following reaction?
A) 
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
31) What is the major product for the following reaction?
A) 
B) 
C) 
D) 
E) More than one of these choices.
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Medium
32) Dehydrohalogenation of tert-pentyl bromide at higher temperatures will produce 2-methyl-1-butene as the chief product when:
A) CH3COONa is employed as the base.
B) KOH/C2H5OH is employed as the base
C) CH3CH2ONa/CH3CH2OH is employed as the base.
D) (CH3)3COK/(CH3)3COH is employed as the base.
E) any base is used, as long as the temperature is sufficiently high.
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6
Difficulty Level: Medium
33) What is the major product for the following reaction?
A) 
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Hard
34) What is the major product for the following reaction?
A) 
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Hard
35) What is the major product for the following reaction?
A)
B)
C)
D) 
E)
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Medium
36) What is the major product for the following reaction?
A)
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
37) What is the major product for the following reaction?
A)
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
38) What is the major product for the following reaction?
A)
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 6.5, 7.6
Difficulty Level: Hard
39) Which compound listed below would you expect to be the major product when 2-bromo-2-methylbutane is refluxed with KOH/ethanol?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 6.5, 7.3, 7.6
Difficulty Level: Medium
40) Zaitsev's rule states that:
A) In electrophilic addition of an unsymmetrical reagent to an unsymmetrical alkene, the more positive portion of the reagent will become attached to the carbon of the double bond bearing the greater number of hydrogen atoms.
B) An equatorial substituent in cyclohexane results in a more stable conformation than if that substituent were axial.
C) E2 reactions occur only if the -hydrogen and leaving group can assume an anti-periplanar arrangement.
D) When a reaction forms an alkene, and several possibilities exist, the more (or most) stable isomer is the one which predominates.
E) The order of reactivity of alcohols in dehydration reactions is 3º > 2º > 1º.
Topic: Alkene Synthesis
Section: 7.6
Difficulty Level: Easy
41) Regarding the use of potassium tert-butoxide as a base in E2 reactions, it is incorrect to state that:
A) this base is more effective than ethoxide ion, because it (KOt-Bu) is the more basic of the two.
B) it tends to give the anti-Zaitsev, i.e., Hofmann, product.
C) it is more reactive in dimethyl sulfoxide than it is in tert-butyl alcohol.
D) it favors E2 reactions over competing SN2 reactions.
E) it will form, predominantly, the more stable alkene.
Topic: Alkene Synthesis
Section: 7.6, 7.7
Difficulty Level: Easy
42) What is the major product of the reaction,
A) (CH3)2C=C(CH3)2
B) (CH3)3C–CH=CH2
C) (CH3)2C=CHCH3
D) (CH3)2C=CHCH2CH3
E) None of these choices.
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Easy
43) Which compound would be the major product?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Easy
44) What are the major product(s) formed when cis-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?
A) I
B) II
C) I and II
D) III
E) III and IV
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Hard
45) What are the major product(s) formed when trans-1-bromo-2-methylcyclohexane reacts with sodium isopropoxide in isopropanol?
A) I
B) II
C) I and II
D) III
E) III and IV
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Hard
46) Which statement(s) is/are true of acid-catalyzed alcohol dehydrations?
A) Protonation of the alcohol is a fast step.
B) Formation of a carbocation from the protonated alcohol is a slow step.
C) Rearrangements of less stable carbocations to more stable carbocations are common.
D) Loss of a proton by the carbocation intermediate is a fast step.
E) All of these choices.
Topic: Carbocation Stability, Rearrangement
Section: 7.10, 7.11
Difficulty Level: Easy
47) Which product(s) would be produced by acid-catalyzed dehydration of 2-methyl-2-pentanol?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.10
Difficulty Level: Easy
48) Which one of the following alcohols would dehydrate most rapidly when treated with sulfuric acid?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
49) Which mechanistic step in the acid-catalyzed dehydration of 3,3-dimethyl-2-butanol is the rate determining step?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
50) Which alcohol would be most easily dehydrated?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
51) Which alcohol would be most easily dehydrated?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
52) Which of the following alcohols would probably undergo dehydration using 25% sulfuric acid below 100 oC?
A) II, IV, V
B) I, II, III
C) III and IV
D) III, IV, V
E) all can be dehydrated
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
53) Which alcohol would initially produce the most stable carbocation when treated with concentrated H2SO4?
A) 
B) 
C) 
D) 
E) 
Topic: Carbocation Stability
Section: 7.10
Difficulty Level: Medium
54) Carbocations are frequent intermediates in acidic reactions of alkenes, alcohols, etc. What do carbocations usually do? They may:
A) rearrange to a more stable carbocation.
B) lose a proton to form an alkene.
C) combine with a nucleophile.
D) react with an alkene to form a larger carbocation.
E) do all of these choices.
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.10, 7.11
Difficulty Level: Hard
55) Which of the following carbocations would NOT be likely to undergo rearrangement?
A) 
B) 
C) 
D) 
E) 
Topic: Carbocation Stability, Rearrangement
Section: 7.11
Difficulty Level: Easy
56) Neopentyl alcohol, (CH3)3CCH2OH, cannot be dehydrated to an alkene without rearrangement. What is the chief product of dehydration?
A) I
B) II
C) III
D) IV
E) V
Topic: Carbocation Stability, Rearrangement
Section: 7.11
Difficulty Level: Hard
57) What is the major product of the reaction between methanol and (2R,3S)-2-bromo-3-methylpentane at room temperature?
A) 
B) 
C) 
D) 
E) Two of these choices.
Topic: Carbocation Stability, Rearrangement
Section: 5.12, 6.10, 7.9, 7.11
Difficulty Level: Medium
58) Rearrangements are likely to occur in which of the following reaction types?
A) SN1 reactions
B) SN2 reactions
C) E1 reactions
D) E2 reactions
E) Both SN1 and E1 reactions
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.9, 7.11
Difficulty Level: Easy
59) What is the major product of the following reaction?
A) 
B) 
C) 
D) 
E) More than one of these choices.
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.8, 7.11
Difficulty Level: Easy
60) What is the major product for the following reaction?
A)
B)
C)
D)
E) More than one of these choices.
Topic: Alkene Synthesis
Section: 6.10, 7.6, 7.8, 7.11
Difficulty Level: Easy
61) What is the major product for the following reaction?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 6.10, 7.6, 7.8, 7.11
Difficulty Level: Medium
62) What is the major product for the following reaction?
A)
B)
C)
D)
E)
Topic: Alkene Synthesis
Section: 7.8, 7.11
Difficulty Level: Medium
63) What is the major product of the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.8, 7.11
Difficulty Level: Hard
64) What is the major product of the following reaction?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.8, 7.11
Difficulty Level: Hard
65) What is the major product of the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.8, 7.11
Difficulty Level: Hard
66) What is the major product(s) of the following reaction sequence?
A) 
B) 
C) 
D) 
E) A mixture of two of these choices.
Topic: Carbocation Stability, Rearrangement
Section: 4.16, 6.10, 7.3, 7.8, 7.11
Difficulty Level: Medium
67) Which alkene would you expect to be the major product of the following dehydration?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements
Section: 7.10, 7.8, 7.11
Difficulty Level: Medium
68) What will be the major product of the following reaction?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis, Reaction Mechanisms, Carbocation Rearrangements
Section: 7.10, 7.8, 7.11
Difficulty Level: Medium
69) Which of the following reactions would yield 3,3-dimethyl-1-butene in a reasonable percentage yield (i.e., greater than 50%)?
A) 
B) 
C)
D) All of these choices.
E) Only two of these choices.
Topic: Alkene Synthesis, Nomenclature
Section: 7.6, 7.10
Difficulty Level: Medium
70) Which reaction would yield 2-butyne?
A) CH3CC:Na + CH3Br
B) CH3CH2Br + HCC:Na
C) CH3:Na + HCCCH3
D) More than one of these choices.
E) None of these choices.
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Easy
71) Which reaction conditions would not yield 2-butyne from 1-propyne?
A) 
B) 
C) 
D) 
E) More than one of these choices.
Topic: Alkyne Synthesis
Section: 3.6, 7.12, 7.14
Difficulty Level: Hard
72) Which of the following reactions would yield 2-pentyne?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Easy
73) Which of the following methods could be used to synthesize 4,4-dimethyl-2-hexyne?
A) 
B) 
C) 
D) More than one of these choices.
E) None of these choices.
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
74) Which statement is/are true about acetylide anions?
A) The alkylated product is poor with secondary alkyl halides.
B) Primary alkyl halides are best suited for alkylation.
C) In the presence of tertiary alkyl halides, the acetylide anion acts as base to give an elimination product.
D) Only two of these statements are true.
E) All of the statements are true.
Topic: Alkyne Synthesis
Section: 7.12, 7.14
Difficulty Level: Easy
75) Which reaction would not result in alkylation of the acetylide anion as the major products?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
76) Which reaction would not primarily proceed via an SN2 mechanism?
A) 
B) 
C) 
D) 
E) All of them proceed via SN2
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
77) Which would be the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 3.16, 7.12, 7.17
Difficulty Level: Easy
78) An unknown compound, B, has the molecular formula C7H12. On catalytic hydrogenation 1 mol of B absorbs 2 mol of hydrogen and yields 2-methylhexane. B has significant IR absorption band at about 3300 and 2200 cm-1. Which compound best represents B?
A) 3-methyl-1-hexyne
B) 5-methyl-2-hexyne
C) 5-methyl-1,3-hexadiene
D) 5-methyl-1-hexyne
E) 2-methyl-1,5-hexadiene
Topic: Structure Elucidation
Section: 2.16, 4.16, 7.17
Difficulty Level: Medium
79) A compound X with the formula C7H10 undergoes catalytic hydrogenation to produce a compound Y with the formula C7H14. What could be true of X?
A) X might have one triple bond and one ring.
B) X might have two double bonds and one ring.
C) X might have one double bond and two rings.
D) X might have one double bond and one triple bond.
E) More than one of these choices.
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 2.16, 4.16, 4.17, 7.15, 7.17
Difficulty Level: Easy
80) A compound, C6H10, which reacts with 2 mol of hydrogen over a platinum catalyst and which shows an IR absorption band at approximately 3300 cm-1 could be:
A) I
B) II
C) III
D) IV
E) V
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 2.16, 4.16, 4.17, 7.17
Difficulty Level: Medium
81) What is the structure of a compound with formula C6H10 which has IR absorption at approximately 3300 cm-1 and which can be catalytically reduced with hydrogen to 2-methylpentane?
A) 
B) 
C) 
D) 
E) 
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 2.16, 4.16, 4.17, 7.17
Difficulty Level: Medium
82) Upon catalytic hydrogenation with platinum, a compound C6H6 absorbs four moles of hydrogen. Select a structure for C6H6.
A) I, II
B) III
C) II, III
D) IV, V
E) I, IV, V
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 4.16, 4.17, 7.16, 7.17
Difficulty Level: Easy
83) What will be the index of hydrogen deficiency in product of cholesterol undergoing catalytic hydrogenation with Pt?
A) 1
B) 2
C) 4
D) 5
E) none of these choices
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 4.16, 4.17, 7.15
Difficulty Level: Medium
84) Which would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Reactions, Reaction Mechanisms
Section: 4.16, 7.15, 7.16
Difficulty Level: Medium
85) Which would be the major product of the following reaction sequence?
A) 
B) 
C) 
+ enantiomer
D) 
E) 
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 7.6, 7.15, 7.16
Difficulty Level: Medium
86. Given: 
One can conclude that X has:
A) no rings and no double bonds.
B) no rings and one double bond.
C) one ring and one double bond.
D) two rings and no double bonds.
E) one triple bond.
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 4.16, 4.17, 7.15
Difficulty Level: Easy
87) On hydrogenation with platinum, a compound C9H12 absorbs 2 mol of hydrogen. Which of the following is a possible structure for the compound?
A) I
B) II
C) III
D) IV
E) V
Topic: Index of Hydrogen Deficiency, Catalytic Hydrogenation
Section: 4.16, 4.17, 7.15, 7.17
Difficulty Level: Easy
88) What is the major product for the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene Synthesis
Section:7.15, 7.17
Difficulty Level: Medium
89) Which would be the major product of the following reaction sequence?
A) (CH3CH2)2C=C=CHT
B) (CH3CH2)2C=C=CH2
C) (CH3CH2)2CHCCT
D) (CH3CH2)2CHCH=CHT
E) None of these choices.
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 3.16, 7.15, 7.17
Difficulty Level: Medium
90) What is the major product for the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.12, 7.14, 7.17
Difficulty Level: Medium
91) What is the major product for the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.12, 7.14, 7.17
Difficulty Level: Medium
92) Which is not a satisfactory procedure for the synthesis of 3-methyl-1-butene?
A) (CH3)2CHCCH3 + conc. H2SO4
B) (CH3)2CHCCH + Li/liq.NH3
C) (CH3)2CHCH2CH2Br + CH3ONa/CH3OH
D) (CH3)2CHCHBrCH3 + (CH3)3COK/(CH3)3COH
E) (CH3)2CHCCH + H2/Ni2B (P-2)
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.10, 7.17
Difficulty Level: Medium
93) What is the major product for the following reaction sequence?
A) 
B) 
C) 
D) 
E) 
Topic: Alkene Synthesis
Section: 7.10, 7.14
Difficulty Level: Medium
94) What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.10, 7.14
Difficulty Level: Medium
95) What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.11, 7.11, 7.14
Difficulty Level: Medium
96) What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.11, 7.11, 7.14
Difficulty Level: Medium
97) What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.11, 7.11, 7.14
Difficulty Level: Medium
98) What is the major product for the following reaction sequence?
A)
B)
C)
D)
E) None of these choices.
Topic: Alkene Synthesis
Section: 7.11, 7.11, 7.14
Difficulty Level: Medium
99) Which of these is the most satisfactory method for the preparation of cis-2-pentene?
A) CH3CHBrCH2CH2CH3 + (CH3)3COK/(CH3)3COH
B) CH3CCCH2CH3 + H2, Pt
C) CH3CCCH2CH3 + H2, Ni2B (P-2)
D) CH3CCCH2CH3 + Li/liq. NH3
E) CH3CH2CHBrCH2CH3 + CH3CH2ONa/CH3CH2OH
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.10, 7.12, 7.14
Difficulty Level: Easy
100) Which reaction would not be a method for preparing 5-methyl-1-hexyne?
A) 
B) 
C) 
D) 
E) 
Topic: Alkyne Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.12, 7.14
Difficulty Level: Easy
101) Which of the following reductions of an alkyne is NOT correct?
A) 2-Pentyne + 2H2/Pt 🡪 pentane
B) 2-Pentyne + H2/Ni2B 🡪 Z-2-Pentene
C) 2-Pentyne + Li/NH3(l) 🡪 Z-2-Pentene
D) All of these answer choices are correct.
E) None of these answer choices are correct.
Topic: Alkyne Reduction, Nomenclature, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Easy
102) The structure of the product, C, of the following sequence of reactions would be:
A) 
B) 
C) 
D) 
E) 
Topic: Alkyne Synthesis, Catalytic hydrogenation
Section: 7.11, 7.14
Difficulty Level: Medium
103) Which would be the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Medium
104) Which would be the major product of the following reaction sequence?
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 6.5, 7.10, 7.11, 7.14
Difficulty Level: Hard
105) Predict the major organic product(s) of the following reaction:
A) I, II
B) III, V
C) I, IV
D) only V
E) None of these choices.
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 6.5, 7.10, 7.11, 7.14
Difficulty Level: Hard
106) Which of the following compounds could be produced from the following reaction sequence?
A) I
B) II
C) III
D) IV
E) mixture of III and IV
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 6.5, 7.10, 7.11, 7.14
Difficulty Level: Easy
107) Predict the major organic product(s) of the following reaction:
A) I, II
B) III, V
C) I, IV
D) only V
E) None of these choices.
Topic: Alkene/Alkyne Reactions, Reaction Mechanisms
Section: 6.5, 7.12, 7.14
Difficulty Level: Hard
108) The structure of the product obtained from 2-butyne and Li/C2H5NH2 is:
A) 
B) 
C) 
D) 
E) 
Topic: Dissolving Metal Reduction; trans-hydrogenation
Section: 7.17
Difficulty Level: Easy
Question type: True/False
109) In dehydrohalogenation reactions the Zaitsev product will always be the major product produced in the reaction.
Topic: Dehydrohalogenation of alkyl halides
Section: 7.6
Difficulty: Medium
110) In dehydration reactions the Zaitsev product will almost always be the major product produced in the reaction.
Topic: Dehydration of alcohols
Section: 7.10, 7.11
Difficulty: Medium
111) Tertiary carbocations will form the fastest because they have a transition state that is the lowest in free energy.
Topic: Carbocation stability and transition states
Section: 7.11
Difficulty: Easy
112) The main reason why anti-periplaner conformation is preferred in E2 reactions is because the conformation of the hydrogen that is anti to the leaving group provides for a staggered transition state, which is lower in free energy.
Topic: Stereochemistry of E2 reactions
Section: 7.6, 7.7
Difficulty: Hard
113) In acid catalyzed dehydration of alcohol, the acid catalyst is always regenerated in the reaction process.
Topic: Dehydration of alcohols
Section: 7.10
Difficulty: Medium
114) Alkenes and alkynes that are saturated must have an index of hydrogen deficiency equal to zero as they have no carbon-carbon pi electron present in the system.
Topic: Catalytic hydrogenation
Section: 7.15, 7.16, and 7.17
Difficulty: Easy
Question type: molecular drawing
115) Draw the structures of all stereoisomers of 2-chloro-4-methyl-3-hexene, clearly showing all stereochemical details, using appropriate 3-D representations (dash-wedge, etc.) as relevant.
Topic: Nomenclature, Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
Question type: essay
116) The ambiguous name dimethylcyclopentene does not clearly distinguish between several structures.
a) Draw the structures of all constitutional isomers corresponding to this name.
b) Indicate which of these is likely to be the most stable, i.e, have the smallest heat of combustion, justifying your rationale briefly.
c) Which of these structures represents an achiral molecule?
b) Structure I is likely to be the most stable, because it is a tetra-substituted alkene: II, IV and V are tri-substituted; III and VI are di-substituted.
c) Structure I is achiral
Topic: Alkene Nomenclature, Relative Stability
Section: 4.5, 7.3
Difficulty Level: Hard
Question type: fill-in-the-blank
117) When an elimination reaction gives the most stable alkene as the major product, we say that the elimination follows ___’s rule.
Topic: General Information
Section: 7.6
Difficulty Level: Easy
118) When an elimination reaction gives the less substituted alkene as the major product, we say that the elimination follows ___'s rule.
Topic: General Information
Section: 7.7
Difficulty Level: Easy
119) In a dehydration reaction, the leaving group is ___.
Topic: General Information
Section: 7.6
Difficulty Level: Easy
120) Dehydration of alcohols requires a ___ catalyst.
Topic: General Information
Section: 7.10
Difficulty Level: Easy
Question type: molecular drawing
121) Provide a mechanistic explanation for the formation of the observed products in the following reaction.
Topic: Carbocation Rearrangement, Alkene Synthesis, Dehydration Mechanism
Section: 7.10, 7.11
Difficulty Level: Medium
Question type: essay
122) Propose a two-step synthetic strategy for the synthesis of 2-methylhexane from 5-methyl-2-hexanol.
Step 1:
Acid-catalyzed dehydration of 5-methyl-2-hexanol to yield an isomeric mixture of 5-methyl-1-hexene and 5-methyl-2-hexene
Step 2:
Catalytic hydrogenation of the double bond with H2, Ni to yield the desired 2-methylhexane
Topic: Nomenclature, Multistep Synthesis
Section: 4.16, 7.10
Difficulty Level: Hard
Question type: fill-in-the-blank
123) Carbocations have three options available for further reaction. These options include reaction with a nucleophile, loss of a beta proton to give an alkene, and ___.
Topic: General Information
Section: 7.11
Difficulty Level: Medium
Question type: molecular drawing
124) Draw an arrow-pushing mechanism to justify the following transformation:
Topic: Dehydration of Alcohols
Section: 7.10, 7.11
Difficulty Level: Hard
125) What “new”, more stable, carbocation(s) may be formed when the following carbocation undergoes spontaneous rearrangement?
Topic: Carbocation Stability, Rearrangement
Section: 7.11
Difficulty Level: Medium
Question type: essay
126) Complete the following reaction sequence, providing a brief rationale for your answer.
Reaction with PCl5 would afford a geminal dihalide I, which would undergo E2 elimination when heated, losing 2 moles of HCl to afford the alkyne III. However, since III is a terminal alkyne, it has a hydrogen atom that is labile in presence of NaNH2; hence, an extra mole equivalent of the base is required to ensure complete reaction and convert all of the initially formed III into the sodium alkynide intermediate, II; this, upon acidification, affords the final alkyne product III.
Topic: Alkyne Synthesis, Acid-Base reactions
Section: 7.12, 7.13
Difficulty Level: Medium
Question type: fill-in-the-blank
127) Alkynes can be produced from either ___ or ___ dihalides.
Topic: General Information
Section: 7.6
Difficulty Level: Medium
128) In hydrogenation reactions, both hydrogen atoms add to the pi system from the same face of the molecule. This is an example of a(n) ___ addition.
Topic: General Information
Section: 7.16
Difficulty Level: Easy
129) Catalytic hydrogenation utilizing palladium, platinum or nickel proceeds through a process known as ___ catalysis as the metal catalyst is not soluble in the reaction mixture.
Topic: Alkene Hydrogenation
Section: 7.16
Difficulty Level: Easy
130) How will you prepare cis-1,2-dimethylcyclohexane from 1,2-dimethylcyclohexene?
Topic: Alkene Hydrogenation
Section: 7.16
Difficulty Level: Easy
Question type: essay
131) The IR spectrum of an unknown substance Q, C9H16, is found to have distinct peaks at 3310 cm-1 and 2140 cm-1. Treatment of Q with excess H2 in presence of Raney Ni affords nearly quantitative yields of 2,3-dimethylheptane. Propose a reasonable structure for Q, based on the above information, briefly explaining your rationale. Also give its IUPAC name.
The Index of Hydrogen deficiency of Q is 2 (compared with C9H20). The IR data suggests that Q is a terminal alkyne; thus, there must be no rings in its structure. The catalytic hydrogenation data provides further details of the carbon skeleton. Due to the specific substitution pattern in this carbon skeleton, there is only one possible position for a terminal triple bond. Thus, the structure given above is consistent with all of the given information.
IUPAC Name: 5,6-dimethyl-1-heptyne
Topic: Nomenclature, Index of Hydrogen Deficiency, IR Spectroscopy, Catalytic Hydrogenation
Section: 2.16, 7.17
Difficulty Level: Medium
Question type: fill-in-the-blank
132) Syn hydrogenation of an alkyne will produce a ___ alkene.
Topic: General Information
Section: 7.17
Difficulty Level: Easy
133) Conversion of alkynes to E-alkenes (trans-alkenes) can be accomplished via a ___ reaction.
Topic: General Information
Section: 7.17
Difficulty Level: Medium
Question type: essay
134) How will you prepare trans-2-heptene from 2-heptyne?
Topic: Alkyne Reduction
Section: 7.17
Difficulty Level: Medium
Question type: molecular drawing
135) Complete the following reaction, giving structural details of all intermediates as well as the final product.
Topic: Alkyne Synthesis, Alkyne Hydrogenation
Section: 7.12, 7.14, 7.17
Difficulty Level: Medium
Question type: essay
136) Propose a reasonable synthetic strategy for the synthesis of trans-6-methyl-3-heptene from 4-methyl-1-pentyne.
Step 1:
Add NaNH2/NH3(l) to selectively deprotonate the alkyne hydrogen.
Step 2:
Add ethyl iodide to give 6-methyl-3-pentyne by an SN2 process.
Step 3:
Add Na(s)/NH3(l) to give the desired trans-alkene by dissolving metal reduction.
Topic: Nomenclature, Multistep Synthesis
Section: 7.12, 7.14, 7.17
Difficulty Level: Medium
Question type: fill-in-the-blank
137) The process by which one works a synthesis problem backwards to the point where reagentscan be easily acquired is known as ___.
Topic: Organic Synthesis
Section: 7.18
Difficulty level: Easy
Question type: molecular drawing
138) Write a retrosynthetic analysis of the compound cis-1-butenylcyclohexane from vinylcyclohexane and then write a forward synthesis showing all necessary reagents and relevant intermediates.
Topic: Organic Synthesis
Section: 7.18
Difficulty level: Hard
139) Which of the following reactions proceeds with inversion of configuration at the carbon bearing the leaving group?
A) SN2
B) SN1
C) E2
D) E1
E) All of these answer choices are correct.
Topic: Stereochemistry of SN/E reactions
Sections: 6.8, 6.12, and 7.9
Difficulty Level: Easy
140) Consider the substitution reaction that takes place when (R)-3-bromo-3-methylhexane is treated with sodium methoxide. Which of the following would be true?
A) An SN2 reaction would take place with inversion of configuration at the stereogenic center.
B) An SN1 reaction would take place with retention of configuration at the stereogenic center.
C) An SN1 reaction would take place with racemization of configuration at the stereogenic center.
D) An SN1 reaction would take place, accompanied by an E1 reaction, affording a complex mixture of products.
E) An E2 reaction would take place, during which the stereogenic center is lost.
Topic: Predicting mechanism, stereochemistry of SN reactions
Sections: 6.8, 6.12, 7.9
Difficulty Level: Medium
141) Consider the substitution reaction that takes place when (R)-3-iodo-3-methylheptane is treated with sodium acetate (CH3CO2Na). Which of the following would be true?
A) An SN2 reaction would take place with inversion of configuration at the stereogenic center.
B) An SN1 reaction would take place with retention of configuration at the stereogenic center.
C) An SN1 reaction would take place with racemization of configuration at the stereogenic center.
D) An SN1 reaction would take place, accompanied by an E1 reaction, affording a complex mixture of products.
E) An E2 reaction would take place, during which the stereogenic center is lost.
Topic: Predicting mechanism, stereochemistry of SN reactions
Sections: 6.8, 6.12, 7.9
Difficulty Level: Medium
142) By analyzing the starting material and the product(s), the following reaction is an example of what type of mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) More than one of these choices.
Topic: Predicting mechanisms, products
Section: 6.13, 7.9
Difficulty Level: Easy
143) By analyzing the starting material and the product(s), the following reaction is an example of what type of mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 6.13, 7.9
Difficulty Level: Easy
144) By analyzing the starting material and the product(s), the following reaction is an example of what type of mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 6.13, 7.9
Difficulty Level: Easy
145) When 1,4-diiodo-2,2-dimethylbutane (0.10 mol) is treated with 0.10 mol of NaCN in dimethyl sulfoxide at 30C, the product formed is:
A) 
B) 
C) 
D) 
Topic: Predicting mechanisms, products
Section: 6.13, 7.9
Difficulty Level: Medium
146) By analyzing the starting material and the product(s), the following reaction is possibly an example of what type of mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) More than one of these choices.
Topic: Predicting mechanisms, products
Section: 6.13, 7.9
Difficulty Level: Hard
147) You want to synthesize 3-methyl-2-pentene from 2-chloro-3-methylpentane. Which reagent would you use?
A) HCl, heat
B) NH3(aq), 25oC
C) CH3CO2Na, CH3CO2H, heat
D) CH3CH2ONa, CH3CH2OH, heat
E) CH3CH2OH, heat
Topic: Synthesis, reagent selection
Section: 6.13, 7.9
Difficulty Level: Hard
148) By analyzing the starting material and the product, the following reaction is possibly an example of what type of mechanism(s)?
A) SN1
B) SN2
C) E1
D) E2
E) More than one of the above
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
149) Which mechanism best describes the chemical process shown below?
a) SN2
b) E1
c) E2
d) SN1
e) None of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
150) By analyzing the starting material and the product(s), the following reaction is an example of what type of mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
151) By analyzing the starting material and the product(s), the following reaction is possibly an example of what type of mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.9
Difficulty Level: Hard
152) Which alkyl halide, when treated with sodium ethoxide in ethanol, would afford a product mixture consisting of more than one elimination product?
A) 1-bromo-3,3-dimethylpentane
B) 1-bromo-2,3-dimethylpentane
C) 2-bromo-3,4-dimethylpentane
D) 2-bromo-3,3-dimethylpentane
E) None of these choices would yield more than one elimination product.
Topic: Predicting products
Section: 7.9
Difficulty Level: Medium
153) Elimination reactions are favored over nucleophilic substitution reactions
A) at high temperatures.
B) when tert-butoxide ion is used.
C) when 3 alkyl halides are used as substrates.
D) when nucleophiles are used which are strong bases and the substrate is a 2 alkyl halide.
E) in all of these cases.
Topic: Generalities
Section: 7.9
Difficulty Level: Medium
154) What would you expect to be the chief organic product(s) when tert-butyl bromide reacts with sodium acetylide, i.e.,
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Hard
155) What would you expect to be the chief organic product(s) when 2-bromo-2-methylpentane react(s) with sodium propynide, i.e.,
A) I
B) II
C) III
D) IV
E) V
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Hard
156) Suggest a reagent to perform the following transformation:
a) NaOH, H2O
b) NaH, THF
c) NaOMe, MeOH
d) t-butoxide, t-butanol
e) Ethanol
Topic: Predicting reagents for mechisms
Section 7.9
Difficulty: Medium
157) What major product(s) are likely to be obtained from the following reaction?
A) I, by predominantly SN2
B) II, by predominantly SN2
C) an equimolar mixture of I and II, by predominantly SN1
D) III, by substitution of the alkyl group, rather than substitution of the chloro group.
E) Actually, none of these products are likely to be obtained as major products, because elimination will probably predominate, leading to the formation of an alkene.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
158) The major product(s) of the following reaction is(are):
A) I
B) II
C) III
D) IV
E) Equal amounts of I and II.
Topic: Predicting mechanisms, products
Section: 6.8 and 7.9
Difficulty Level: Easy
159) What would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) An equimolar mixture of I and II.
Topic: Predicting products
Section: 6.8 and 7.9
Difficulty Level: Easy
160) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Section: 6.8 and 7.9
Difficulty Level: Easy
161) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Predicting products
Section: 6.8 and 7.9
Difficulty Level: Easy
162) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Sections: 6.8 and 7.9
Difficulty Level: Easy
163) What would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) Equal amounts of I and III.
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Easy
164) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Easy
165) Reaction of sodium ethoxide with 1-bromopentane at 30C yields primarily:
A) CH3CH2CH2CH=CH2
B) CH3CH2CH=CHCH3
C) CH3CH2CH2CH2CH3
D) CH3CH2CH2CH2CH2OH
E) CH3CH2CH2CH2CH2OCH2CH3
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Easy
166) Heating an alcoholic solution of sodium hydroxide and 1-bromopentane at 60C yields primarily:
A) 
B) 
C) 
D) 
E) 
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Medium
167) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Section: 6.8, 7.9
Difficulty Level: Medium
168) What would be the major product(s) of the following reaction?
A) I and II
B) I, II, and III
C) III
D) I, II, and IV
E) None of these choices.
Topic: Predicting products
Section: 6.8, 7.9
Difficulty Level: Medium
169) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) More than one of these choices
Topic: Synthesis, reagent selection
Sections: 6.8, 7.9
Difficulty Level: Medium
170) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) A mixture of two of these choices
Topic: Synthesis, reagent selection
Sections: 6.8, 7.9
Difficulty Level: Medium
171) When 0.10 mol of ICH2CH2CH2CH2Cl reacts with 0.10 mol of NaOCH3 in CH3OH at 40C, the major product is:
A) CH3OCH2CH2CH2CH2Cl
B) CH3OCH2CH2CH2CH2I
C) CH3OCH2CH2CH2CH2OCH3
D) CH2=CHCH2CH2Cl
E) CH2=CHCH2CH2I
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Medium
172) If 0.10 mol of HSCH2CH2OH reacts at 25C, sequentially, with 0.20 mol of NaH, 0.10 mol of CH3CH2Br followed by the addition of H2O, which is the major product?
A) HSCH2CH2OCH2CH3
B) CH3CH2SCH2CH2OH
C) CH3CH2SCH2CH2OCH2CH3
D) CH2=CH2
E) CH3CH3
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Hard
173) What would be the major product obtained when trans-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25oC?
A) I
B) II
C) III
D) IV
E) Equal amounts of I and II.
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Hard
174) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Hard
175) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Synthesis, reagent selection
Sections: 6.8, 7.9
Difficulty Level: Medium
176) The major product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 6.8, 6.13, 7.9
Difficulty Level: Hard
177) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Predicting products
Sections: 6.8, 6.14, 7.9
Difficulty Level: Medium
178) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Section: 6.8, 6.14, 7.9
Difficulty Level: Medium
179) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Synthesis, reagent selection
Sections: 6.8, 6.14, 7.9
Difficulty Level: Medium
180) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Synthesis, reagent selection
Sections: 6.8, 6.14, 7.9
Difficulty Level: Hard
181) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Predicting products
Section: 7.5 and 7.9
Difficulty Level: Easy
182) What would be the major product(s) of the following reaction?
A) I and II
B) II and III
C) III and IV
D) I and IV
E) All of these choices.
Topic: Predicting products
Section: 7.10 and 7.9
Difficulty Level: Easy
183) Which of these compounds would give the largest E2/SN2 product ratio on reaction with sodium ethoxide in ethanol at 55°C?
A) 
B)
C)
D) 
E) 
Topic: Predicting mechanisms
Sections: 6.8, 7.9
Difficulty Level: Medium
184) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Predicting products
Sections: 7.5, 7.6, 7.9
Difficulty Level: Easy
185) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.5, 7.6, 7.9
Difficulty Level: Easy
186) The major product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.9
Difficulty Level: Easy
187) What would be the major product(s) of the following reaction?
A) I and III
B) I and II
C) II and III
D) IV
E) None of these choices.
Topic: Predicting products
Sections: 7.9
Difficulty Level: Medium
188) What would be the major product(s) of the following reaction?
A) I
B) II
C) III and IV
D) I and II
E) All of these choices.
Topic: Predicting mechanisms, products
Sections: 7.9
Difficulty Level: Medium
189) What would be the major product(s) of the following reaction?
A) I
B) II, III, and IV
C) III and IV
D) II and IV
E) IV and III
Topic: Predicting products
Sections: 7.5, 7.6, 7.9
Difficulty Level: Medium
190) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.5, 7.6, 7.9
Difficulty Level: Medium
191) Predict the major product(s) for the following reaction sequence.
A) A mixture of 
and 
B) 
C) 
D) 
E) A mixture of two of these choices.
Topic: Synthesis, reagent selection
Sections: 7.5, 7.6, 7.9
Difficulty Level: Hard
192) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Synthesis, reagent selection
Sections: 7.5, 7.6, 7.9
Difficulty Level: Hard
193) Treating (CH3)3C-Cl with a mixture of H2O and CH3OH at room temperature would yield:
A) CH2=C(CH3)2
B) (CH3)3COH
C) (CH3)3COCH3
D) All of these choices.
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
194) Treating 1-bromo-1-methylcyclohexane with CH3OH at room temperature would yield:
A) 
B) 
C) 
D) All of these choices.
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
195) Which would be formed in the following reaction?
A) I
B) II
C) III
D) IV
E) All of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Medium
196) What would be the major product(s) of the following reaction?
A) I and II
B) II and III
C) I and III
D) IV
E) None of these choices.
Topic: Predicting products
Section: 6.12 and 7.9
Difficulty Level: Medium
197) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Section: 6.12 and 7.9
Difficulty Level: Medium
198) What would be the major product(s) of the following reaction?
A) I and II
B) I, II, and III
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Sections: 6.12 and 7.9
Difficulty Level: Medium
199) When tert-pentyl chloride undergoes solvolysis in aqueous ethanol at room temperature, there is/are formed:
A) 
B) 
C) 
D) 
E) All of these choices.
Topic: Predicting mechanisms, products
Sections: 6.12 and 7.9
Difficulty Level: Medium
200) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Section: 6.12, 6.14, 7.9
Difficulty Level: Medium
201) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 6.12, 7.8, 7.9
Difficulty Level: Easy
202) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Sections: 6.14, 7.5, 7.8, 7.9
Difficulty Level: Easy
203) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Easy
204) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Easy
205) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Easy
206) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Predicting products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Medium
207) What would be the major product(s) of the following reaction?
A) I
B) II and III
C) II, III, and IV
D) III and IV
E) None of these choices.
Topic: Predicting products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Medium
208) What would be the major product(s) of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Medium
209) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Medium
210) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) A mixture of two of these choices.
Topic: Synthesis, reagent selection
Sections: 7.5, 7.8, 7.9
Difficulty Level: Medium
211) Which would be the major product of the following reaction?
A) I
B) II
C) III
D) IV
E) None of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Easy
212) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 6.12 and 7.9
Difficulty Level: Hard
213) The product(s) for the following reaction would mainly be dictated by which mechanism?
A) SN1
B) SN2
C) E1
D) E2
E) None of these choices.
Topic: Predicting mechanisms, products
Sections: 7.5, 7.8, 7.9
Difficulty Level: Hard
214) Which would be formed in the following reaction?
A) I
B) II
C) III
D) IV
E) All of these choices.
Topic: Predicting mechanisms, products
Section: 7.9
Difficulty Level: Hard
215) Predict the major product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) A 1:1 mixture of two of these choices. )
Topic: Synthesis, reagent selection
Sections: 6.8, 7.9 then 6.12
Difficulty Level: Hard
216) Predict the product(s) for the following reaction sequence.
A) 
B) 
C) 
D) 
E) None of these choices.
Topic: Synthesis, reagent selection
Sections: 7.5, 7.7, 7.9
Difficulty Level: Hard
217) Heating tert-butyl chloride with 1.0 M NaOH in a mixture of water and methanol would yield mainly
A) (CH3)3COH through an SN1 reaction.
B) (CH3)3COCH3 through an SN1 reaction.
C) (CH3)3COH through an SN2 reaction.
D) (CH3)3COCH3 through an SN2 reaction.
E) CH2=C(CH3)2 through an E2 reaction.
Topic: Predicting mechanism, products
Sections: 7.9
Difficulty Level: Hard
218) All SN1 reactions will always be accompanied by a competing E1 reaction.
Topic: E1 reactions
Section: 7.9
Difficulty Level: Medium
219) Give a detailed reaction mechanism for the reaction expected to occur when 2-bromo-2-methylpentane is heated with methanol. Draw clear structural formulas of all relevant species and use curved arrows to represent electron flow. Also indicate which step is likely to be rate-determining.
Topic: Predicting reaction mechanisms
Sections: 7.5, 7.8, 7.9
Difficulty Level: Medium
220) When diastereomers I and II undergo an E2 elimination on treatment with sodium ethoxide in ethanol, one of the isomers react 500 times faster than the other one. Also, one isomer gives only A as a product and the other isomer gives a mixture of A and B as products. Determine the products of each isomer and explain your reasoning.
Topic: Predicting reaction mechanisms
Sections: 7.5, 7.7
Difficulty Level: Hard
221) Even though sodium ethoxide is a strong nucleophile and a strong base, only one major product is observed in the reaction below. Explain why.
Topic: Predicting reaction mechanisms
Sections: 7.5, 7.7
Difficulty Level: Medium
222) Which structure represents (R,E)-5-methylhept-2-ene?
A)
B)
C)
D)
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
223) Which structure represents (S,E)-5-methylhept-2-ene?
A)
B)
C)
D)
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
224) Which structure represents (S,Z)-5-methylhept-2-ene?
A)
B)
C)
D)
E) None of these choices.
Topic: Nomenclature; Stereochemistry
Section: 4.3, 4.5, 5.7, 7.2
Difficulty Level: Hard
225) Which product (or products) would be formed in appreciable amount(s) when cis-1-bromo-2-methylcyclohexane undergoes dehydrohalogenation upon treatment with sodium ethoxide in ethanol?
A) I
B) II
C) III
D) IV
E) More than one of these choices.
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 7.6
Difficulty Level: Medium
226) Which compound listed below would you expect to be the major product when 2-bromo-2-methylbutane is refluxed with t-BuOK/t-BuOH?
A)
B)
C)
D)
E)
Topic: Alkene Synthesis, Reaction Mechanisms
Section: 6.5, 7.3, 7.6
Difficulty Level: Medium
227) Which one of the following alcohols would dehydrate least rapidly when treated with sulfuric acid?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
228) Which alcohol would be least easily dehydrated?
A) I
B) II
C) III
D) IV
E) V
Topic: Alkene Synthesis; Alcohol Dehydration
Section: 7.10
Difficulty Level: Easy
229) Rearrangements are unlikely to occur in which of the following reaction types?
A) SN1 reactions
B) SN2 reactions
C) E1 reactions
D) E2 reactions
E) Both SN2 and E2 reactions
Topic: Carbocation Stability, Rearrangement
Section: 6.10, 7.9, 7.11
Difficulty Level: Easy
230) What is the major product of the following reaction?
A) 2,3-dimethyl-2-butene
B) 3,3-dimethyl-1-butene
C) 2,3-dimethyl-1-butene
D) 3,3-dimethyl-1-butyne
E) None of these choices.
Topic: Alkene Synthesis, Nomenclature
Section: 7.6, 7.10
Difficulty Level: Medium
231) What is the major product of the following reaction?
A) 2,3-dimethyl-2-butene
B) 3,3-dimethyl-1-butene
C) 2,3-dimethyl-1-butene
D) 3,3-dimethyl-1-butyne
E) None of these choices.
Topic: Alkene Synthesis, Nomenclature
Section: 7.6, 7.10
Difficulty Level: Medium
232) What is the major product of the following reaction?
A) 2,3-dimethyl-2-butene
B) 3,3-dimethyl-1-butene
C) 2,3-dimethyl-1-butene
D) 3,3-dimethyl-1-butyne
E) None of these choices.
Topic: Alkene Synthesis, Nomenclature
Section: 7.6, 7.10
Difficulty Level: Medium
233) What is the major product of the following reaction?
A) 1-pentyne
B) 2-pentyne
C) 1-pentene
D) 2-pentene
E) None of these choices
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Easy
234) What is the major product of the following reaction?
A) 1-pentyne
B) 2-pentyne
C) 1-pentene
D) 2-pentene
E) None of these choices
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Easy
235) What is the major product of the following reaction?
A) 1-pentyne
B) 2-pentyne
C) 1-pentene
D) 2-pentene
E) None of these choices
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Easy
236) What is the major product of the following reaction?
A) 1-pentyne
B) 2-pentyne
C) 1-pentene
D) 2-pentene
E) None of these choices
Topic: Alkene Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.12, 7.14
Difficulty Level: Easy
237) What is the major product of the following reaction?
A) 4,4-dimethyl-1-hexyne
B) 4,4-dimethyl-2-hexyne
C) 3,3-dimethyl-2-hexyne
D) 2-methyl-1-butene
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
238) What is the major product of the following reaction?
A) 4,4-dimethyl-1-hexyne
B) 4,4-dimethyl-2-hexyne
C) 3,3-dimethyl-2-hexyne
D) 2-methyl-1-butene
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
239) What is the major product of the following reaction?
A) 4,4-dimethyl-1-hexyne
B) 4,4-dimethyl-2-hexyne
C) 3,3-dimethyl-2-hexyne
D) 2-methyl-1-butene
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
240) Which statement is/are false about acetylide anions?
A) The alkylated product is poor with secondary alkyl halides.
B) Primary alkyl halides are best suited for alkylation.
C) In the presence of tertiary alkyl halides, the acetylide anion acts as base to give an elimination product.
D) Only two of these statements are true.
E) None of the statements are false.
Topic: Alkyne Synthesis
Section: 7.12, 7.14
Difficulty Level: Easy
241) What is the major product of the following reaction?
A) 1-propyne
B) 2-hexyne
C) hex-1-en-4-yne
D) 7,7-dimethyloct-2-yne
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
242) What is the major alkyne product of the following reaction?
A) 1-propyne
B) 2-hexyne
C) hex-1-en-4-yne
D) 7,7-dimethyloct-2-yne
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
243) What is the major product of the following reaction?
A) 1-propyne
B) 2-hexyne
C) hex-1-en-4-yne
D) 7,7-dimethyloct-2-yne
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
244) What is the major product of the following reaction?
A) 1-propyne
B) 2-hexyne
C) hex-1-en-4-yne
D) 7,7-dimethyloct-2-yne
E) None of these choices
Topic: Alkyne Synthesis
Section: 7.14
Difficulty Level: Medium
245) What is the major product of the following reaction?
A) 5-methyl-1-hexyne
B) 5-methyl-2-hexyne
C) 4-methyl-1-hexyne
D) 4-methyl-2-hexyne
E) None of these choices
Topic: Alkyne Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.12, 7.14
Difficulty Level: Easy
246) What is the major product of the following reaction?
A) 5-methyl-1-hexyne
B) 5-methyl-2-hexyne
C) 4-methyl-1-hexyne
D) 4-methyl-2-hexyne
E) None of these choices
Topic: Alkyne Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.12, 7.14
Difficulty Level: Easy
247) What is the major product of the following reaction?
A) 5-methyl-1-hexyne
B) 5-methyl-2-hexyne
C) 4-methyl-1-hexyne
D) 4-methyl-2-hexyne
E) None of these choices
Topic: Alkyne Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.12, 7.14
Difficulty Level: Easy
248) What is the major product of the following reaction?
A) 5-methyl-1-hexyne
B) 5-methyl-2-hexyne
C) 4-methyl-1-hexyne
D) 4-methyl-2-hexyne
E) None of these choices
Topic: Alkyne Synthesis, Nomenclature, Reaction Mechanisms
Section: 7.6, 7.12, 7.14
Difficulty Level: Easy
249) Reaction of sodium tert-butoxide with 1-bromopentane at 30C yields primarily:
A) CH3CH2CH2CH=CH2
B) CH3CH2CH=CHCH3
C) CH3CH2CH2CH2CH3
D) CH3CH2CH2CH2CH2OH
E) CH3CH2CH2CH2CH2OCH2CH3
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Easy
250) Reaction of potassium hydroxide with 1-bromopentane at 30C yields primarily:
A) CH3CH2CH2CH=CH2
B) CH3CH2CH=CHCH3
C) CH3CH2CH2CH2CH3
D) CH3CH2CH2CH2CH2OH
E) CH3CH2CH2CH2CH2OCH2CH3
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Easy
251) What would be the major product obtained when cis-1-bromo-3-methylcyclopentane is allowed to react with NaSH at 25oC?
A) I
B) II
C) III
D) IV
E) Equal amounts of I and II.
Topic: Predicting mechanisms, products
Sections: 6.8, 7.9
Difficulty Level: Hard