Deck 12: Nucleophilic Substitution and Elimination Reactions 2: Reactions That Are Useful for Synthesis

Question 1

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A racemic mixture of I and II

Answer 1

III

Question 2

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A racemic mixture of I and II

Answer 2

III

Question 3

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A racemic mixture of I and II

Answer 3

III

Question 4

Which is true about the following reaction?

A)It will produce an equal mixture of enantiomers.
B)It will produce an unequal mixture of enantiomers.
C)It will produce an equal mixture of diastereomers.
D)It will produce an unequal mixture of diastereomers.
E)It will produce a racemic mixture.

Question 5

Which of the following reagents can complete the reaction below?

A)NaBr
B)HBr
C)PBr₃
D)b and c
E)a, b, and c

Question 6

What is the most likely product of the following reaction?

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

Question 7

Identify the reagent(s)needed to complete the following reaction scheme.

A)CH₂N₂
B)CH₃NH₂
C)KOCH₃
D)NaOCH₃
E)HOCH₃, NaOH

Question 8

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A racemic mixture of I and II

Question 9

Which is true about the following reaction?

A)Its mechanism requires a carbocation rearrangement.
B)It will produce (S)-2-chlorobutane exclusively.
C)It will produce (R)-2-chlorobutane exclusively.
D)A racemic mixture will result.
E)Its mechanism includes a nucleophilic addition step.

Question 10

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)An equal mix of III and IV
E)An equal mix of II and IV

Question 11

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)No reaction will occur.

Question 12

Which of the following mechanism steps is required in the creation of epoxides from halohydrins?

A)Proton transfer
B)E1
C)E2
D)Nucleophilic addition
E)Nucleophile elimination

Question 13

Which of the following mechanism steps is required in Williamson ether synthesis?

A)Nucleophilic addition
B)Nucleophile elimination
C)E2
D)S_N2
E)Carbocation rearrangement

Question 14

Identify the reagent(s)needed to complete the following reaction scheme.

A)NaOH, Cl₂
B)HOAc, Cl₂
C)PCl₃
D)HCl
E)NaCl

Question 15

What is the most likely product of the following reaction?

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

Question 16

What is the most likely product of the following reaction?

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

Question 17

What is the most likely product of the following reaction?

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

Question 18

What is the most likely product of the following reaction?

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

Question 19

What is the most likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of I and II

Question 20

What is the most likely product of the following reaction?

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

Question 21

What is the product of the following reaction?

A)I
B)II
C)III
D)IV
E)No reaction will occur.

Question 22

Which of the following mechanistic steps is required in the creation the following ether?

A)E1
B)electrophilic addition
C)nucleophilic addition
D)heterolysis
E)carbocation rearrangement

Question 23

Draw the product of the following reaction.

Question 24

What is the most likely product of the following reaction?

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

Question 25

Identify the reagent(s)needed to complete the following reaction scheme.

A)HOCH₂CHCH₂
B)NaH followed by BrCH₂CHCH₂
C)H₂O followed by BrCH₂CHCH₂
D)KOCH₂CHCH₂
E)None of these will work.

Question 26

Draw the product of the following reaction.

Question 27

What is the likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of I and II

Question 28

Show the reagent(s)needed to complete the following reaction.

Question 29

Draw the product of the following reaction.

Question 30

What is the most likely product of the following reaction?

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

Question 31

Explain why halogenation occurs twice in the following reaction.

Question 32

Draw the product of the following reaction.Pay attention to stereochemistry,if applicable.

Question 33

What is the product of the following reaction?

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

Question 34

Show the reagent(s)needed to complete the following reaction.

Question 35

Draw the product(s)of the following reaction.Pay attention to stereochemistry,if applicable.

Question 36

Draw the product of the following reaction.Pay attention to stereochemistry,if applicable.

Question 37

Draw the product of the following reaction.

Question 38

Show how (S)-4-methylpentan-2-ol can be converted into (S)-2-chloro-4-methylpentane.

Question 39

What is the likely product of the following reaction?

A)I
B)II
C)III
D)IV
E)A mixture of I and II

Question 40

Draw the product of the following reaction.

Question 41

Show how the following ether can be synthesized from an alcohol.

Question 42

Show how the following halohydrin can be synthesized from an epoxide.

Question 43

Give the product of the following reaction.

Question 44

Synthesize the following ether from any alcohol and alkyl halide.

Question 45

Draw a Lewis structure for CH₂N₂.

Question 46

Draw the product of the following reaction.

Question 47

Draw a detailed mechanism for the following transformation.

Question 48

Give the product of the following reaction.

Question 49

Draw the product of the following reaction.

Question 50

Supply a detailed mechanism,including arrows,for the following reaction.

Question 51

Draw the product of the following reaction.

Question 52

Give the name of the functional group present in the molecule below.

Question 53

Draw a detailed mechanism for the following reaction,and show the product.

Question 54

What is the product of the following reaction?

Question 55

Provide the product and draw a detailed mechanism for the following reaction.

Question 56

Provide the product of the following reaction.

Question 57

Draw the reagent(s)needed to complete the following reaction.

Question 58

Show the reagents and conditions needed to complete the following reaction.