Deck 8: Alkenes and Alkynes II

Question 1

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.

Answer 1

I and II

Question 2

The thermodynamic parameters at 298 K for the following reaction are given below.
$\Delta$ Hº = -64.9 kJ mol^-1 Which of the following statements is true of the reaction?

A)Both $\Delta$ Hº and $\Delta$ Sº favor product formation.
B)Neither $\Delta$ Hº nor $\Delta$ 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 $\Delta$ Gº indicates that the reaction cannot occur as written.

Answer 2

The entropy term is unfavorable but the formation of ethyl chloride is favored.

Question 3

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Answer 3

Question 4

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 5

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 6

What are the major product(s)formed by treating treating methylcyclopentene with HBr and MeO-OMe?

A)II
B)III
C)Two of these choices.
D)None of these choices.

Question 7

What are possible products for the following reaction?

A)
B)
C)
D)Two of these choices.
E)None of these choices.

Question 8

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)None of these choices.

Question 9

Treating 1-methylcyclohexene with HCl would yield primarily which of these?

A)I
B)II
C)III
D)IV
E)V

Question 10

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

Question 11

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 12

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 13

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 14

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

Question 15

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)More than one of these choices.

Question 16

The interaction of the $\pi$ bond of an alkene with an electrophile can initially result in the formation of a species termed a $\pi$ complex.Which of these cannot combine with an alkene to form a $\pi$ complex?

A)H⁺
B)NH₃
C)Ag⁺
D)Hg²⁺
E)BF₃

Question 17

(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

Question 18

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)None of these choices.

Question 19

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.

Question 20

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

Question 21

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 22

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

Question 23

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

Question 24

What is the major product for the following reaction?

A)
B)
C)
D)
E)None of these choices.

Question 25

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 26

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.

Question 27

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 28

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

Question 29

Which product would you expect from the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 30

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)More than one of these choices.

Question 31

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

Question 32

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.

Question 33

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 34

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

Question 35

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)An equal mixture of two of these choices.

Question 36

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)More than one of these choices.

Question 37

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.

Question 38

What is the major product for the following reaction?

A)
B)
C)
D)
E)None of these choices.

Question 39

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

Question 40

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 41

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 42

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

Question 43

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.

Question 44

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

Question 45

What is the major product for the following reaction?

A)
B)
C)
D)All of these choices are major products.
E)A mixture of two of these choices.

Question 46

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.

Question 47

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)

Question 48

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.

Question 49

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 50

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.

Question 51

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)None of these choices.

Question 52

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)More than one of these choices.

Question 53

What is the major product for the following reaction?

A)
B)
C)
D)
E)None of these choices.

Question 54

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 55

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 56

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 57

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.

Question 58

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 59

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.

Question 60

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)

Question 61

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

Question 62

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.

Question 63

Which reaction is NOT stereospecific?

A)I
B)II
C)III
D)IV
E)V

Question 64

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

Question 65

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)None of these choices.

Question 66

What is the major product for the following reaction?

A)
B)
C)
D)
E)None of these choices.

Question 67

What is the major product for the following reaction?

A)
B)
C)
D)
E)

Question 68

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

Question 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

Question 70

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 71

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

Question 72

What is the major product of the following reaction sequence?

A)
B)
C)
D)
E)More than one of these choices.

Question 73

Which of these compounds will react with cold concd.H₂SO₄,as well as Br₂ in CCl₄?

A)CH₃CH₂CH=CHCH₃
B)CH₃CH₂CH₂CH=CH₂
C)CH₃CH₂C $\equiv$ CCH₃
D)(CH₃)₂CHC $\equiv$ CH
E)All of these choices.

Question 74

What would be the major product of the following reaction?

A)I
B)II
C)III
D)IV
E)V

Question 75

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 76

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 77

Which reagent(s)given below could be used to synthesize cis-1,2-cycloheptanediol from cycloheptene?

A)KMnO₄,OH^-0,5^oC
B)KMnO₄,H₃O⁺,75^oC
C)H₂SO₄,heat
D)All of these choices.
E)None of these choices.

Question 78

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 79

What is the major product for the following reaction?

A)
B)
C)
D)
E)More than one of these choices.

Question 80

What product would result from the following reaction?

A)I
B)II
C)III
D)IV
E)V