Deck 7: Substitution Reactions

Question 1

What is the nucleophile in the following reaction?

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

Answer 1

II

Question 2

What is the correct structure for 3-ethyl-1-iodocyclohexane?

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

Answer 2

I

Question 3

What is the IUPAC name for the following compound?

A) 1,2-bromocyclopentane
B) (1R, 2S)-1,2-dibromocyclopentane
C) (1S, 2S)-1,2-dibromocyclopentane
D) (1S, 2R)-1,2-dibromocyclopentane
E) (1R, 2R)-1,2-dibromocyclopentane

Answer 3

(1S, 2S)-1,2-dibromocyclopentane

Question 4

For the following reaction, label the nucleophile, electrophile, and leaving group.

Question 5

Which of the following is a substitution reaction?

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

Question 6

For the following reaction, label the nucleophile, electrophile, and leaving group.

Question 7

What is the IUPAC name for the following compound?

A) Chlorocyclopentane
B) 2-Chloro-1-methylcyclopentane
C) 1-Methyl-2-chlorocyclopentane
D) 1-Chloro-2-methylcyclopentane

Question 8

Which of the following is a substitution reaction?

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

Question 9

What is the IUPAC name for the following compound?

Question 10

What is the electrophile in the following reaction?

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

Question 11

What is the IUPAC name for the following compound?

A) 3-Fluorobutane
B) 2-Fluorobutane
C) (S)-2-Fluorobutane
D) (R)-2-Fluorobutane

Question 12

What is the correct structure for 2-bromo-3-methylbutane?

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

Question 13

Provide the structure for 1-chloro-4-isopropylheptane.

Question 14

What is the nucleophile in the following reaction?

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

Question 15

What is the IUPAC name for the following compound?

Question 16

What is the electrophile in the following reaction?

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

Question 17

What is the correct structure for (2S,5R)-2-fluoro-5-methylnonane?

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

Question 18

What is the IUPAC name for the following compound?

A) 2-Bromo-4-pentylhexane
B) (2S,4S)-2-Bromo-4,5-diethylheptane
C) 3,4-Diethyl-6-bromoheptane
D) 2-Bromo-4-methylhexane
E) (2R,4R)-2-Bromo-4,5-diethylheptane

Question 19

What is the IUPAC name for the following compound?

Question 20

Which of the following is a substitution reaction?

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

Question 21

Provide a curved arrow mechanism for the following reaction.

Question 22

Which of the following is the rate equation for the following S_N2 reaction?

A) Rate = k[1-bromopropane]
B) Rate = k[NaCN]
C) Rate = k[1-bromopropane] [NaCN]
D) Rate = k[1-bromopropane]²
E) Rate = k[1-bromopropane]² [NaCN]²

Question 23

Provide a curved arrow mechanism for the following reaction

Question 24

Which of the following is a reasonable definition of a concerted reaction?

A) it is a reaction in which bond breaking occurs first
B) it is a reaction in which all bond-breaking and bond-forming occurs at the same time
C) it is a reaction in which bond forming occurs first
D) it is a substitution reaction

Question 25

Which of the following is a secondary alkyl halide?

A) 1-Bromo-2-methylpropane
B) 2-Bromopropane
C) 1-Bromobutane
D) 2-Bromo-2-methylpropane

Question 26

Which of the following is a primary alkyl halide?

A) (CH₃)₂CHCH₂Cl
B) (CH₃)₂CClCH₂CH₃
C) (CH₃)₂CHCHClCH₃
D) (CH₃)₂CHCH₂CCl(CH₃)₂

Question 27

Provide a curved arrow mechanism for the following reaction.

Question 28

Which of the following is a tertiary alkyl halide?

A) 1-Bromo-2-methylpropane
B) 2-Bromopropane
C) 1-Bromobutane
D) 2-Bromo-2-methylpropane

Question 29

Which of the following is a tertiary alkyl halide?

A) (CH₃)₂CHCH₂Cl
B) (CH₃)₂CClCH₂CH₃
C) (CH₃)₂CHCHClCH₃
D) (CH₃)₂CHCH₂CHClCH₂CH₃

Question 30

Provide the structure for cis-1,2-dibromocyclopentane.

Question 31

When drawing a curved arrow mechanism, the tail of the arrow starts at______.

A) the bond that is being formed
B) the atom with the positive charge
C) the source of electrons that is being moved
D) the location to which the electrons are being moved

Question 32

Which of the following is not a possible step in a substitution reaction?

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

Question 33

Provide a curved arrow mechanism for the following reaction.

Question 34

Provide a curved arrow mechanism and predict the product for the following reaction.

Question 35

Which of the following is the rate equation for the following reaction? CH₃CH₂CH₂CHBrCH₃ + NaN₃ $\rightarrow$ CH₃CH₂CH₂CHN₃CH₃ + NaBr

A) Rate = k[CH₃CH₂CH₂CHBrCH₃]
B) Rate = k[NaN₃]
C) Rate = k[CH₃CH₂CH₂CHBrCH₃] [NaBr]
D) Rate = k[CH₃CH₂CH₂CHBrCH₃] [NaN₃]
E) Rate = k[CH₃CH₂CH₂CHBrCH₃]² [NaN₃]

Question 36

What is the classification for the following halide?

A) primary halide
B) secondary halide
C) tertiary halide
D) quaternary halide

Question 37

Provide the structure for (4R,8S)-4-iodo-2,2,8-trimethyldecane.

Question 38

Provide a curved arrow mechanism and predict the product for the following reaction.

Question 39

Which of the following is a secondary alkyl halide?

A) (CH₃)₂CHCH₂Cl
B) (CH₃)₂CClCH₃
C) (CH₃)₂CHCHClCH₃
D) (CH₃)₂CHCH₂CCl(CH₃)₂

Question 40

When drawing a curved arrow mechanism, the head of the arrow goes to____.

A) the bond that is being formed
B) the bond that is being broken
C) the source of electrons that is being moved
D) the location to which the electrons are being moved

Question 41

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) None of these

Question 42

Predict the product for the following reaction.

A) I
B) II
C) III
D) IV
E) None of these

Question 43

Consider the following S_N2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of NaN₃ is tripled?

A) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) It would increase the rate six times

Question 44

Draw the transition state for the following reaction.

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

Question 45

Draw the potential energy diagram for the following reaction.

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

Question 46

Which of the following alkyl halides will undergo the fastest S_N2 reaction?

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

Question 47

Predict the product for the following S_N2 reaction.

A) I
B) II
C) III
D) IV
E) Both I & II

Question 48

Rank the following compounds from most to least reactive in an S_N2 reaction.

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

Question 49

Rank the following compounds from most to least reactive in an S_N2 reaction.

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

Question 50

Consider the following S_N2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 2-bromopentane is doubled and the concentration of CH₃CH₂COONa is halved?

A) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) It would reduce by half

Question 51

Which of the following alkyl halides is essentially unreactive in an S_N2 reaction?

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

Question 52

Which of the following is the rate equation for the following S_N1 reaction?

A) Rate = k[H₂O]
B) Rate = k[1-chloro-1-methylcyclohexane] [H₂O]
C) Rate = k[chloride ion]
D) Rate = k[1-chloro-1-methylcyclohexane]

Question 53

Predict the product for the following reaction.
(1R, 3S)-1-bromo-3-sec-butilcyclopentane + NaN₃

Question 54

Which of the following alkyl halides will undergo the slowest S_N2 reaction?

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

Question 55

Consider the following S_N2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of 1-chloro-3-methylbutane is doubled?

A) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) It would reduce by half

Question 56

Predict the product for the following S_N2 reaction.

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

Question 57

Which of the following potential energy diagram represent an exothermic concerted reaction?

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

Question 58

Draw the transition state for the following reaction.
(S)-1-iodo-3-methylpentane +NaSCH₃

Question 59

Consider the following S_N2 reaction, Assuming no other changes, what is the effect on the rate, if the concentration of both 1-chloro-3-methylbutane and NaN₃ is doubled?

A) No effect
B) It would double the rate
C) It would triple the rate
D) It would increase four times
E) It would reduce by half

Question 60

Which of the following is a mechanism for an S_N2 reaction?

A) I
B) II
C) III
D) IV
E) Both I & II

Question 61

Which of the following is the rate equation for the following reaction? 2-chloro-2-methylpentane + NaI

A) Rate = k[NaI]
B) Rate = k[2-chloro-2-methylpentane] [NaI]
C) Rate = k[chloride ion]
D) Rate = k[2-chloro-2-methylpentane]

Question 62

Predict the product for the following S_N1 reaction.

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

Question 63

Which of the following compounds will undergo the fastest S_N1 reaction? Explain your choice.

Question 64

Predict the product(s) for the following reaction.

A) Both I & IV
B) II
C) III
D) IV
E) Both II & III

Question 65

Provide a curved arrow mechanism for the following reaction.

Question 66

Predict the product(s) for the following reaction.

Question 67

Which of the following is true about the stereochemistry of S_N1 reaction?

A) retention of configuration at the electrophilic center
B) inversion of configuration at the electrophilic center
C) 50:50 mixture of retention and inversion of configuration at the electrophilic center
D) slightly more inversion than retention at the electrophilic center
E) slightly more retention than inversion at the electrophilic center

Question 68

Rank the following compounds from most to least reactive in an S_N1 reaction.

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

Question 69

Predict the product for the following S_N1 reaction.

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

Question 70

Rank the following compounds from most to least reactive in an S_N1 reaction.

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

Question 71

Draw the potential energy diagram for the following reaction.

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

Question 72

Which of the following alkyl halides will undergo the slowest S_N1 reaction?

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

Question 73

Predict the major product for the following reaction and provide a curved arrow mechanism for the formation of the product.

Question 74

Predict the product(s) for the following reaction.

Question 75

Predict the product for the following S_N1 reaction.

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

Question 76

Provide a curved arrow mechanism for the following reaction.

Question 77

Predict the major product for the following reaction.

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

Question 78

Which of the following compounds will undergo the fastest S_N1 reaction?

A) I
B) II
C) III
D) IV
E) Both I & IV

Question 79

Which of the following alkyl halides will undergo the fastest S_N1 reaction?

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

Question 80

Which of the following potential energy diagram represent an exothermic S_N1 reaction?

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