Deck 7: Alkyl Halides: Nucleophilic Substitution and Elimination Reactions

Question 1

Which of the following is a primary alkyl halide?

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

Answer 1

(CH₃)₂CHCH₂Cl

Question 2

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

Answer 2

(2S,4S)-2-Bromo-4,5-diethylheptane

Question 3

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

Answer 3

Question 4

What is the nucleophile in the following reaction?

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

Question 5

What is the nucleophile in the following reaction?

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

Question 6

Which of the following is a substitution reaction?

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

Question 7

Which of the following is an elimination reaction?

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

Question 8

Which of the following is an elimination reaction?

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

Question 9

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 10

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 11

What is the electrophile in the following reaction?

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

Question 12

What is the electrophile in the following reaction?

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

Question 13

Which of the following is a tertiary alkyl halide?

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

Question 14

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 15

Which of the following is a substitution reaction?

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

Question 16

What is the IUPAC name for the following compound?

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

Question 17

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

Question 18

Which of the following is a substitution reaction?

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

Question 19

Which of the following is a secondary alkyl halide?

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

Question 20

What is the classification for the following halide?

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

Question 21

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

Question 22

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 23

What is the IUPAC name for the following compound?

Question 24

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 25

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 26

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

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 27

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

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

Question 28

What is the IUPAC name for the following compound?

Question 29

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

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

Question 30

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

Question 31

What is the IUPAC name for the following compound?

Question 32

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

Question 33

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 34

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 35

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

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

Question 36

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 37

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 38

Provide a curved arrow mechanism for the following S_N2 reaction

Question 39

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

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

Question 40

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

Question 41

Predict the product for the following S_N2 reaction.

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

Question 42

Draw the transition state for the following S_N2 reaction.

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

Question 43

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

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

Question 44

Draw the transition state for the following S_N2 reaction.

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

Question 45

Predict the product for the following S_N2 reaction.

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

Question 46

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 47

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 48

Provide a curved arrow mechanism and predict the product for the following S_N2 reaction.

Question 49

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

Question 50

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

Question 51

Predict the product for the following reaction.

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

Question 52

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

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

Question 53

Predict the product for the following reaction.

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

Question 54

Draw the potential energy diagram for the following S_N2 reaction.

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

Question 55

Predict the product for the following reaction.

Question 56

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 57

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 58

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

Question 59

Predict the product for the following S_N2 reaction.

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

Question 60

Predict the product for the following S_N2 reaction.

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

Question 61

Predict the product for the following S_N2 reaction.

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

Question 62

Identify the IUPAC name for the following compound.

A) 1-methyl-2-cyclohexene
B) 2-methylcyclohexene
C) 3-methylcyclohexene
D) 1-methyl-5-cyclohexene

Question 63

Identify the methylating agent used in biological systems.

A) methyl iodide
B) S-adenosylmethionine
C) methylalanine
D) methylproline
E) methyl bromide

Question 64

Which of the following is a protic solvent?

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

Question 65

Describe a strong nucleophile.

A) an anion
B) a cation
C) a radical
D) a neutral compound

Question 66

Which of the following is NOT a nucleophile?

A) OH^-
B) NH₃
C) CH₃OH
D) NH₄⁺
E) All of these

Question 67

Which of the following is a strong nucleophile?

A) OH^-
B) H₂O
C) CH₃OH
D) NH₄⁺
E) All of these

Question 68

Which of the following is a weak nucleophile?

A) OH^-
B) H₂O
C) CH₃O^-
D) NH₄⁺
E) All of these

Question 69

Identify which of the following that is NOT an effect of adrenaline.

A) increases heart rate
B) elevates sugar level
C) provides boost of energy
D) increases level of oxygen
E) makes one sleepy

Question 70

Provide an IUPAC name for the following compound.

Question 71

Which of the following is the IUPAC name for the following compound?

A) 2-ethyl-1,1,3-trimethylbutene
B) 3-ethyl-2,4-dimethyl-2-pentene
C) 2,4-dimethylhexene
D) 4-ethyl-1,3-dimethyl-3-pentene

Question 72

Predict the product for the following S_N2 reaction.

Question 73

Which of the following shows a mechanism of a concerted elimination?

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

Question 74

Predict the S_N2 product and provide a curved arrow mechanism for the formation of the product.

Question 75

What set of reaction conditions would favor an S_N2 reaction on 2-bromo-3-methylbutane?

A) weak nucleophile in a protic solvent
B) weak nucleophile in an aprotic solvent
C) strong nucleophile in a protic solvent
D) strong nucleophile in an aprotic solvent

Question 76

Which of the following is an aprotic solvent?

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

Question 77

Identify the type of elimination in an E2 mechanism.

A) alpha elimination
B) beta elimination
C) gamma elimination
D) delta elimination
E) omega elimination

Question 78

Draw the structure of 2,3-dimethyl-1-pentene.

Question 79

Which of the following describes the difference between protic and aprotic solvents?

A) protic solvents stabilize anions only
B) aprotic solvents stabilize anions only
C) protic solvents stabilize cations only
D) aprotic solvents stabilize both cations and anions
E) protic solvents stabilize both cations and anions

Question 80

Provide a curved arrow mechanism for the following S_N2 reaction.