Deck 7: Substitution Reactions

Question 1

When drawing an arrow-pushing mechanism,the tail of the arrow starts where?

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

Answer 1

At the bond that is being broken.
At the source of electrons that is being moved.

Question 2

Provide an arrow pushing mechanism and product for the following reaction.

Answer 2

Question 3

Provide an IUPAC name for the following compound.

Answer 3

1,1-Dibromocyclopropane

Question 4

Identify the labeled carbon as primary,secondary,or tertiary.

Question 5

What are two features typical of a leaving group?

Question 6

Provide examples of the 4 patterns for steps in the mechanisms of substitution reactions.

Question 7

Provide an IUPAC name for the following compound.

Question 8

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

A)It is a reaction which takes place in a series of steps.
B)It is a reaction which produces a loud noise.
C)It is a reaction in which all bond-breaking and bond-forming occurs at the same time.
D)It is a substitution reaction.

Question 9

Draw an example of a substitution reaction.

Question 10

Which of the following is the correct IUPAC name of the following structure?

A)2-Bromo-3-butylpentane
B)(2S)-Bromo-4,5-dimethylheptane
C)3,4-Dimethyl-6-bromoheptane
D)2-Bromo-4-methylhexane

Question 11

Provide an arrow pushing mechanism for the following reaction.

Question 12

What is the leaving group in the following reaction?

A)Sulfur
B)Carbon
C)Hydrogen
D)Iodide

Question 13

What is the leaving group in the following reaction?

A)carbon
B)bromide
C)hydrogen
D)nitrogen

Question 14

Identify the labeled carbon as primary,secondary,or tertiary.

Question 15

Identify the labeled carbon as primary,secondary,or tertiary.

Question 16

Provide a definition of a concerted reaction.

Question 17

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

Question 18

Which of the following is the correct IUPAC name of the following structure?

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

Question 19

Which of the following is the correct IUPAC name of the following structure?

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

Question 20

On the following compound,label all of the primary,secondary,and tertiary carbons.

Question 21

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

A)A>B>C>D
B)D>C>B>A
C)A>C>B>D
D).D>C>B>A

Question 22

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

A)A>B>C>D
B)C>D>B>A
C)C>B>A>D
D)D>C>B>A

Question 23

What is the product of the following reaction?

Question 24

Provide an arrow-pushing mechanism for the following (intramolecular)reaction.

Question 25

What is the product of the following reaction?

Question 26

Provide the S_N2 product of the following reaction.

Question 27

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

A)A>B>C>D
B)D>C>B>A
C)C>B>A>D
D)D>C>B>A.

Question 28

Given the following rate law,what will happen to the rate if the concentration of MeI is doubled?
Rate = k[Me₃N][MeI]

A)It will be doubled.
B)It will not change.
C)It will decrease in half.
D)It will increase very slightly.

Question 29

Write the rate law for the following S_N2 reaction.

Question 30

Draw a reaction diagram for the following reaction.

Question 31

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

A)
B)
C)
D)

Question 32

From the given starting material,how could you stereospecifically form the given product?

Question 33

Provide a mechanism for this reaction.

Question 34

When drawing an arrow-pushing mechanism,the head of the arrow goes where?

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

Question 35

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

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

Question 36

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

A)A>B>C>D
B)D>C>B>A
C)C>B>A>D
D)D>C>A>B

Question 37

Provide the rate law for the following reaction.

Question 38

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

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

Question 39

Given the following rate law,what will happen to the rate if the concentration of both reactants is doubled?
Rate = k[Me₃N][MeI]

A)It will be doubled.
B)It will not change.
C)It will decrease in half.
D)It will increase 4-fold.

Question 40

Given the following rate law,what will happen to the rate if the concentration of MeI is doubled and the concentration of Me₃N is halved?
Rate = k[Me₃N][MeI]

A)It will be doubled.
B)It will not change.
C)It will decrease in half.
D)It will increase very slightly.

Question 41

Which of the following must be protonated in order to be a good leaving group?

A)Cl
B)Br
C)NMe₂
D)OH₂

Question 42

What is the anticipated major product for the following reaction?

Question 43

What is the mechanism for the following reaction?

Question 44

Draw a reaction diagram for the following S_N1 reaction.

Question 45

Circle the best leaving group in the following compound.

Question 46

What is the best leaving group in the following compound?

Question 47

Provide an example of a nucleophile that will require a proton transfer step at the end of the reaction.

Question 48

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

A)A>B>C>D
B)A>B>D>C
C)D>A>B>C
D)D>C>B>A

Question 49

Why is a tertiary alkyl halide more reactive in an S_N1 reaction than a secondary alkyl halide?

Question 50

Which of the following is a good leaving group?

A)-OH
B)-CH₃
C)-Br
D)-NH₂

Question 51

Draw the anticipated major product for the following reaction.

Question 52

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

A)A>B>C>D
B)A>B>D>C
C)D>A>B>C
D)D>C>B>A

Question 53

Draw a mechanism for the following reaction.

Question 54

Which of the following nucleophiles will require a proton transfer step at the end of the reaction?

A)NMe₃
B)I^-
C)OH^-
D)H₂S

Question 55

Provide a mechanism for the following S_N1 reaction.

Question 56

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

A)A>B>C>D
B)A>B>D>C
C)C>B>A>D
D)D>A>B>C

Question 57

What is the product of the following reaction.Include stereochemistry.

Question 58

Why does a racemate form at the leaving group carbon in an S_N1 reaction?

Question 59

Provide the product of the following reaction.

Question 60

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

A)A>B>C>D
B)A>B>D>C
C)C>A>B>D
D)C>D>B>A

Question 61

For the following reaction,provide an energy diagram.

Question 62

For the following reaction,which of the following is the mechanism?

A)S_N1
B)S_N2
C)Protonation
D)Elimination

Question 63

Is the following nucleophile strong or weak?
I^-

A)Strong
B)Weak
C)Not a nucleophile

Question 64

What set of reaction conditions should favor an S_N1 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 65

What reaction mechanism is most likely for substitution on the following compound?

A)S_N1
B)S_N2
C)Either
D)Neither

Question 66

For the following reaction,provide the mechanism.

Question 67

For the following reaction,which of the following is the mechanism?

A)S_N1
B)S_N2
C)Protonation
D)Elimination

Question 68

What reaction mechanism is most likely for substitution on the following compound?

A)S_N1
B)S_N2
C)Either
D)Neither

Question 69

What set of reaction conditions should 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 70

For the following reaction,draw the product.

Question 71

What reaction mechanism is most likely for substitution on the following compound?

A)S_N1
B)S_N2
C)Either
D)Neither

Question 72

For the following reaction,provide the rate law.

Question 73

What reaction mechanism is most likely for substitution on the following compound?

A)S_N1
B)S_N2
C)Either
D)Neither

Question 74

Draw an energy diagram for the following reaction.

Question 75

What reaction mechanism is most likely for substitution on the following compound?

A)S_N1
B)S_N2
C)Either
D)Neither

Question 76

For the following reaction,which of the following is the rate law?

A)k[HBr]
B)k[1-pentanol]
C)k[HBr][1-pentanol]
D)k[HBr]²

Question 77

What is the rate law for the following S_N1 reaction?

Question 78

Draw an energy diagram for the following reaction.

Question 79

For the following reaction,which of the following is the rate law?

A)Rate = k[MeI]
B)Rate = k[t-butanol]
C)Rate = k[MeI][t-butanol]
D)Rate = k[OH]

Question 80

What reaction mechanism is most likely for substitution on the following compound?

A)S_N1
B)S_N2
C)Either
D)Neither