Deck 20: Nucleophilic Addition to Polar Π Bonds 2: Addition of Weak Nucleophiles and Acid and Base Catalysis

Question 1

What is the most likely product of the following reaction?

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

Answer 1

II

Question 2

Which of the reagents will complete the transformation shown below?

A)I
B)II
C)III
D)IV
E)None of these will complete the reaction.

Answer 2

III

Question 3

What is the most likely product of the following reaction?

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

Answer 3

No reaction will occur.

Question 4

Which of the following is true of the Wolff-Kishner reduction?

A)It always takes place under acidic conditions.
B)It converts ketones to alcohols.
C)It converts aldehydes to alcohols.
D)It converts carbonyls in ketones to a CH₂ group.
E)It requires neutral conditions.

Question 5

What is the most likely product of the following reaction?

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

Question 6

What is the most likely product of the following reaction?

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

Question 7

What functional group is present in the following compound?

A)Amine
B)Imine
C)Enamine
D)Amide
E)Acetal

Question 8

What new functional group is created in the product of the following reaction?

A)Ketone
B)Aldehyde
C)Imine
D)Enamine
E)Acetal

Question 9

What is the most likely product of the following reaction?

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

Question 10

What is the most likely product of the following reaction?

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

Question 11

Which of the following is true of aldol reactions?

A)The thermodynamics and kinetics of aldol reactions can be controlled by base selection.
B)Aldol reactions can be completed by reacting an aldehyde and a ketone in the presence of a base.
C)The yields of aldol reactions involving only one type of α hydrogen are generally higher than the yields of those involving multiple types of α hydrogens.
D)Aldol reactions are used to create carbon-carbon bonds.
E)All of the above are true of aldol reactions.

Question 12

What is the most likely product of the following reaction?

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

Question 13

What is the most likely product of the following reaction?

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

Question 14

Which of the following is true regarding the incomplete reaction scheme below?

A)The reaction can only be completed in acidic conditions.
B)The product is called an acetal.
C)The starting material for this reaction is an aldehyde.
D)The mechanism for this reaction requires a nucleophilic elimination step.
E)The reaction is reversed using excess water and H⁺.

Question 15

When the carbonyl of an aldehyde is protonated with H₂SO₄,which of the following is not true?

A)The protonated aldehyde is more likely to react with alcohols.
B)The protonated carbonyl has a formal charge.
C)The protonated aldehyde becomes more nucleophilic.
D)The protonation of the aldehyde is reversible.
E)The protonated aldehyde is more likely to react with water.

Question 16

Which of the following nucleophiles would add to an α,β-unsaturated ketone via direct addition?

A)KCN
B)KOH
C)Br₂
D)NH₂CH₂CH₂CH₃
E)HOCH₂CH₂CH₃

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

Which of the following functional groups can be hydrolyzed to a carbonyl using excess water in acid?

A)Imine
B)Enamine
C)Acetal
D)Hemiacetal
E)All of the above (a-d)

Question 20

Which of the following functional groups is present in the compound below?

A)Amine
B)Imine
C)Enamine
D)Amide
E)Acetal

Question 21

What is the aldol condensation product for the following reaction?

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

Question 22

Which of the following molecules cannot undergo an intramolecular aldol condensation when treated with NaOH?

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

Question 23

Which base will produce the most kinetic product for an aldol reaction at -78 $\degree$ C?

A)NaN(CH(CH₃)₂)₂
B)NH₃
C)NaOCH₂CH₃
D)H₂O
E)NaOH

Question 24

Give the product of the following reaction.

Question 25

What is the major product for the following reaction?

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

Question 26

What is the product of the following crossed aldol condensation?

A)I
B)II
C)III
D)IV
E)None of these is the crossed aldol product.

Question 27

Give the product and provide a mechanism for the following reaction.

Question 28

What is the aldol condensation product for the following reaction?

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

Question 29

Name the following functional group.

Question 30

Give the starting material that best completes the following reaction.

Question 31

Give the appropriate starting material for the reaction below.

Question 32

What is the major product of the following intramolecular aldol reaction?

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

Question 33

What is the product of the following reaction?

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

Question 34

Give the product for the following reaction.

Question 35

Give the starting reagents required to complete the following reaction.

Question 36

Give the product and provide a mechanism for the following reaction.

Question 37

Which of the following is not true of the Robinson annulation?

A)One of the participants must be an α,β-unsaturated carbonyl.
B)One of the participants must be an α,β-unsaturated carbonyl with at least two acidic hydrogens.
C)Its mechanism requires an intramolecular aldol reaction.
D)Its mechanism requires a Michael reaction.
E)All of the above (a-d) are true.

Question 38

Which compound,in a reaction with the ketone below,would produce the fewest side products?

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

Question 39

What is the product of the following crossed aldol condensation?

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

Question 40

What is the aldol condensation product for the following reaction?

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

Question 41

What is the product of the following reaction?

Question 42

Give the aldol product for the following reaction.

Question 43

Give two possible aldol products for the reaction between the following aldehyde and ketone.

Question 44

What is the product of the following reaction?

Question 45

Give the product and provide a mechanism for the following reaction.

Question 46

Give the compound that when treated with KOH in the presence of heat will produce the following product?

Question 47

Provide the starting material for the following reaction.

Question 48

What is the product of the following reaction?

Question 49

What temperature should be used for the following reaction?

Question 50

Supply the reagents required to complete the following reaction.

Question 51

Give the product and the detailed arrow-pushing mechanism for the following aldol condensation.

Question 52

Provide the product for the following reaction.

Question 53

Give the enolate of the following molecule.

Question 54

Provide the starting material that can be hydrolyzed to produce the following amide.

Question 55

Give the product of the following reaction.

Question 56

Give the reagents that best complete the following reaction.

Question 57

Give the starting material that best completes the following reaction.

Question 58

What starting material can be heated with NaOH to produce the given product?

Question 59

What starting material can be heated with NaOH to produce the given product?

Question 60

Give the product of the following reaction.

Question 61

What starting material is needed to complete the following Robinson annulation?

Question 62

When the following starting materials are treated with NaOH,and a Robinson annulation occurs,what is the product of the reaction?

Question 63

Give the detailed arrow-pushing mechanism for the following reaction.