Deck 8: Alkenes and Alkynes Ii: Addition Reactions

Question 1

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

Answer 1

Two

Question 2

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) More than one of the above

Answer 2

Question 3

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Answer 3

Question 4

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 5

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 the above are reasons.

Question 6

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 the above are equally likely to be formed

Question 7

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 8

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

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

Question 9

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 10

(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 11

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 12

The thermodynamic parameters at 298 K for the following reaction are given below. $\Delta$ Hº = -64.9 kJ mol^-1
$\Delta$ Sº = -131 J K^-1 mol^-1

$\Delta$ Gº = -25.8 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.

Question 13

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 14

What would be the major product of the following reaction?

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

Question 15

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 16

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) None of the above

Question 17

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 the above

Question 18

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) None of the above

Question 19

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 20

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 21

Which product would you expect from the following reaction?

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

Question 22

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 23

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 24

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 25

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) More than one of the above

Question 26

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 27

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-1butene
E) All of these would be equally reactive.

Question 28

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 29

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 30

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) None of the above

Question 31

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 32

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 33

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 34

What is the major product for the following reaction?

A)

B)

C)

D)

E) None of the above

Question 35

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) More than one of the above

Question 36

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 37

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 38

What is the major product for the following reaction?

A)

B)

C)

D)

E) None of the above

Question 39

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 40

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 41

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 42

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) More than one of the above

Question 43

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 44

Which reaction is NOT stereospecific?

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

Question 45

What would be the major product of the following reaction?

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

Question 46

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 47

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

Question 48

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 49

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 the above in equal amounts

Question 50

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

Question 51

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 52

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E)

Question 53

What is the major product for the following reaction?

A)

B)

C)

D)

E) None of the above

Question 54

The reaction of BrCl (bromine monochloride)with 1-methylcyclopentene will produce as the predominant product:

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

Question 55

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 the above in equal amounts

Question 56

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 57

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 58

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 59

What is the major product for the following reaction?

A)

B)

C)

D)

E)

Question 60

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 61

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

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

Question 62

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 63

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 64

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) More than one of the above

Question 65

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

Question 66

Which alkene would react with cold dilute alkaline permanganate solution to form an optically inactive and irresolvable product?

A)

B)

C)

D)

E)

Question 67

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 68

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 69

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 70

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) None of the above

Question 71

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) CH₃CH₂CH₂CH₂CH₂C $\equiv$ CH
B) (CH₃)₂CHCH₂CH₂C $\equiv$ CH
C) CH₃CH₂CH(CH₃)CH₂C $\equiv$ CH
D) CH₃CH₂CH(CH₃)C $\equiv$ CCH₃
E) CH₂=CHCH(CH₃)CH₂CH=CH₂

Question 72

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 the above in equal amounts

Question 73

What product would result from the following reaction?

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

Question 74

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) Two of the above
E) All of the above

Question 75

What is the major product of the following reaction sequence?

A)

B)

C)

D)

E) More than one of the above

Question 76

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

Question 77

Which reaction would yield a meso compound?

A)

B)

C)

D)

E) None of these

Question 78

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

Question 79

What is the major product for the following reaction?

A)

B)

C)

D)

E) More than one of the above

Question 80

What is the major product for the following reaction?

A)

B)

C)

D)

E)