Deck 11: More Additions to Bonds

Question 1

Which of the following is the major product of this reaction?

A)
B)
C)
D)
E)

Answer 1

Question 2

Which of the following statements about the reaction shown here is false?

A) The reaction is a stereospecific syn addition.
B) The reactive intermediate involved in this process is a triplet carbene.
C) The mechanism is concerted.
D) Nitrogen gas is produced in the reaction.
E) The reactive intermediate in this process is a neutral species.

Answer 2

The reactive intermediate involved in this process is a triplet carbene.

Question 3

What was the starting material used to produce the diol shown under the conditions given?

A)
B)
C)
D)
E)

Answer 3

Question 4

Which product will be observed?

A)
B)
C)
D)
E)

Question 5

Which of these molecules is the product of the reaction shown here?

A)
B)
C)
D)
E)

Question 6

which product will be observed?

A)
B)
C)
D)
E)

Question 7

Which product(s) will be observed?

A)
B)
C) Both a and b
D)
E)

Question 8

Which of these structures is a carbene?

A) I
B) II
C) III
D) II and III
E) I, II, and III

Question 9

Which reagent would you use to accomplish the transformation shown here?

A)
B)
C)
D)
E)

Question 10

Select the best reagent to accomplish the transformation shown here.

A)
B)
C)
D)
E)

Question 11

Which product(s) will be observed?

A)
B)
C) Both a and d
D)
E)

Question 12

Which product(s) will be observed?

A)
B)
C)
D)
E) Both a and b

Question 13

Which of these structures is an intermediate in this transformation?

A)
B)
C)
D)
E)

Question 14

Which reagent would you use to accomplish the transformation shown here?

A)
B)
C)
D)
E)

Question 15

Which product will be obsereced?

A)
B)
C)
D)
E) Boh a and b

Question 16

Consider alkenes A and B .

Which of the following is easily accessible from either A or B ?

A)
B)
C)
D)
E) Both c and d

Question 17

Which reagent would you use to accomplish the transformation shown here?

A) Br₂/H₂O
B) HO^-/ H₂O
C) H₃O⁺/ H₂O
D) Hg(OAc)₂ and H₂O, then NaBH₄
E) CF₃CO₃H

Question 18

Which reagent would you use to accomplish the transformation shown here?

A) diazomethane
B) bromoform, then potassium tert-butoxide
C) trifluoroperacetic acid
D) phenylmagnesium bromide in ether, followed by aqueous acid workup
E) osmium tetroxide

Question 19

Which of these molecules is the product of the reaction shown here?

A)
B)
C)
D)
E)

Question 20

Which product will be observed?

A)
B)
C)
D)
E) c and d

Question 21

Draw the products of the following reaction.Show stereochemistry and indicate the stereochemical
relationship of the products to each other.

Question 22

Which of the following conditions and reagents were used to make this compound?

A)
B)
C)
D)
E)

Question 23

Which of the following structures is an enol?

A)
B)
C)
D)
E)

Question 24

Predict the product and draw a mechanism for its formation in the following reaction.Show all lone pairs, curved arrows, and nonzero formal charges.

Question 25

Which enol, when treated with aqueous acid or base, would generate the ketone shown here?

A)
B)
C)
D)
E) Both a and c

Question 26

Which reagent would you use to accomplish the following transformation?

A)
B)
C)
D)
E)

Question 27

Which of the following statements about treatment of an alkyne with sodium metal in ammonia is false?

A) The product of the reaction is a trans alkene.
B) A radical anion is protonated by solvent.
C) This reaction provides the opposite stereochemistry to that of treating an alkyne with H₂ in the presence of Lindlar's catalyst.
D) Sodium amide forms as the reaction proceeds.
E) A single electron is donated by sodium to a orbital in the alkyne.

Question 28

Which of these products would result from complete ozonolysis of (S)-(+) -carvone, followed by oxidative workup? The structure of racemic carvone is shown.

A)
B)
C)
D)
E)

Question 29

Provide an arrow-pushing mechanism for the formation of the product shown.Your mechanism
should include stereochemistry and should result in the specific stereoisomer shown as the
product.Include all lone pairs, curved arrows, and nonzero formal charges.

Question 30

Which of the following molecules do you expect to react fastest with H₂(g) and palladium on charcoal?

A)
B)
C)
D)
E)

Question 31

Starting with an alkene, which of these methods would produce at least one carbonyl compound as the major product? Assume appropriate aqueous workup in all cases.

A) OsO₄
B) H₃O⁺
C) H₂ and Lindlar's catalyst
D) O₃, then H₂O₂
E) Hg(OAc)₂ and H₂O , then NaBH₄

Question 32

Which reagent would you use to accomplish the following transformation?

A) H₂/ Pd on C.
B) H₂/Wilkinson's catalyst
C) CF₃CO₃H
D) Na/ NH₃
E) H₂/ Lindlar's catalyst

Question 33

Draw the products of the following reaction.Show stereochemistry and indicate the
stereochemical relationship of the products to each other.

Question 34

In the presence of aqueous acid or base, enols are converted to ketones or aldehydes.Which of the following carbonyl compounds is produced when the enol shown here is treated with aqueous
Acid?

A)
B)
C)
D)
E)

Question 35

Which of these enols could be generated by treating an alkyne with the reagent shown here, followed by treatment with aqueous, basic hydrogen peroxide?

A)
B)
C)
D)
E) Both a and b

Question 36

How would you make this compound in one step from alkene of formula C₄H₈ ?

Question 37

Which of the following is not a 1,3-dipolar reagent?

A)
B)
C)
D)
E)

Question 38

Which reagent would you use to accomplish the transformation shown here?

A)
B)
C)
D)
E)

Question 39

Which of the following conditions will result in the formation of the molecule shown here?

A)
B)
C)
D)
E) Both b and c will work.

Question 40

Which of these products would result from complete ozonolysis of (R) - (+) -limonene, followed by reductive workup? The structure of racemic limonene is shown.

A)
B)
C)
D)
E)

Question 41

List three ways to accomplish the transformation shown here.

Question 42

Draw a mechanism for the transformation shown.Include all curved arrows, lone pairs of
electrons, and nonzero formal charges.

Question 43

Show how you would make each of the carbonyl compounds shown using the starting material
provided and any reagents of your choice.

Question 44

When the diene shown here is treated with hydrogen and palladium on charcoal for a short reaction time, the alkene on the left is produced. When the same diene is treated with CF₃CO₃H for a short reaction time, the epoxide on the right is produced. Explain the difference in reactivity between the two alkenes.

Question 45

Propose a mechanism for the transformation shown here.

Question 46

Draw the structure of the most stable ozonide that will result when the compound shown here is
treated with ozone.

Question 47

Predict the product of the following transformation, including the correct stereochemistry.

Question 48

Draw the product of the following transformation:

Question 49

Draw a mechanism for the following transformation.Show all lone pairs, curved arrows, and
nonzero formal charges.

Question 50

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.

Question 51

The following transformation was carried out using one enantiomer of diethyl tartrate and the other reagents of the Sharpless asymmetric epoxidation reaction.

Predict the product that would result using the other enantiomer of diethyl tartrate.

Question 52

The molecule shown was the exclusive product of an ozonolysis reaction followed by a reductive
workup.Draw the structures of two possible starting materials that could have been used.

Question 53

Draw the structure of the enol intermediate that would result from the following conditions.

Question 54

Provide two different precursors and the reagents needed to transform them to the compound shown
here.

Question 55

Provide the missing reagents and structures.

Question 56

Explain the difference between a heterogeneous catalyst and a homogeneous catalyst.

Question 57

Provide the missing reagents in the following reaction sequence.

Question 58

Predict the product of the following transformation.

Question 59

Explain the difference between a triplet carbene and a singlet carbene.

Question 60

Propose three different syntheses of the specific enantiomer of the diol shown here.Each
synthesis must involve a different starting material.

Question 61

Devise a multistep synthesis of the target molecule from the given starting material. Show the reagents needed for each step and the product of each step.

Question 62

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.

Question 63

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.

Question 64

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.Assume that the target is racemic; only
one enantiomer is shown.

Question 65

Devise a multistep synthesis of the target molecule from the given starting material.Show the
reagents needed for each step and the product of each step.