Deck 21: Organic Synthesis 2: Intermediate Topics in Synthesis Design,and Useful Reduction and Oxidation Reactions

Question 1

What is the starting material for the following reaction?

A)
B)
C)
D)
E)

Answer 1

Question 2

What is the product of the following reaction sequence?

A)
B)
C)
D)
E)

Answer 2

Question 3

Which of the following is not part of the mechanism for the catalytic hydrogenation of an alkene?

A)Adsorption of hydrogen gas onto metal surface.
B)Formation of C-H bond and liberation of C atom from surface.
C)Adsorption of alkene onto metal surface.
D)Proton transfer from metal to carbon.
E)Liberation of alkane from surface.

Answer 3

Proton transfer from metal to carbon.

Question 4

Which of the following steps involves umpolung?

A)
B)
C)
D)
E)

Question 5

Predict the major product of the following reaction (assume one equivalent of H₂ is present).

A)
B)
C)
D)
E)

Question 6

Which of the following reactions would not function as an effective protection reaction for an alcohol?

A)
B)
C)
D)
E)

Question 7

What is the major product of the following reaction?

A)
B)
C)
D)
E)

Question 8

Which of the following reagents would be the best choice to carry out the synthetic step shown below?

A)
B)
C)
D)
E)

Question 9

In which of the following reactions does a reversal of polarity at a carbon atom take place?

A)
B)
C)
D)
E)

Question 10

Fill in the starting material for the following reaction.

A)
B)
C)
D)
E)

Question 11

Predict the product of the following reaction.

A)
B)
C)
D)
E)

Question 12

Which of the following transformations would require the use of a protecting group? (Reagents are not shown.)

A)
B)
C)
D)
E)

Question 13

What is the missing starting material for the synthesis shown below?

A)
B)
C)
D)
E)

Question 14

What is the major product of the following reaction?

A)
B)
C)
D)
E)

Question 15

Which mechanism step is involved in the protection reaction shown below?

A)Bimolecular elimination
B)Carbocation rearrangement
C)Electrophilic addition
D)Bimolecular nucleophilic substitution
E)Nucleophilic addition

Question 16

Which of the following reaction sequences could be used to synthesize the molecule shown below?

A)
B)
C)
D)
E)

Question 17

Which of the following alkyl halides will not form a Grignard reagent when reacted with magnesium?

A)A
B)B
C)C
D)D
E)E

Question 18

Predict the major product of the following reaction (assume one equivalent of H₂ is present).

A)
B)
C)
D)
E)

Question 19

Which of the following reactions does not utilize a selective reagent?

A)
B)
C)
D)
E)

Question 20

Predict the product of the following reaction sequence.

A)
B)
C)
D)
E)

Question 21

Show how you would synthesize the molecule below using propionaldehyde as the only source
of carbon present in the final product.

Question 22

What is the expected product of the reaction below?

A)
B)
C)
D)
E)

Question 23

Fill in the missing reagent to carry out the following synthetic step.

Question 24

Propose a way to carry out the following transformation beginning with the starting material shown and using any other reagents necessary.

Question 25

Determine the product of the following reaction sequence.

A)
B)
C)
D)
E)

Question 26

A student proposes the following reaction.Explain the issue that this student may encounter,and suggest an alternative route to achieve the same synthetic transformation.

Question 27

Show how you would carry out the following transformation,using any reagents necessary (requires more than one step).

Question 28

Show how to convert the starting material at the left to the desired product at the right.

Question 29

Draw a complete,detailed mechanism for the protection step shown below,and predict the product.

Question 30

Briefly explain why the following reaction would be a poor choice as a way to protect the aldehyde.

Question 31

Show how you would carry out the following transformation,using any reagents necessary.

Question 32

Fill in the boxes with a starting material and reagents to complete the synthetic scheme below.

Question 33

Which would be the best reagent to carry out the reaction shown below?

A)KMnO₄/NaOH
B)H₂CrO₄/H₂SO₄
C)Zn/Hg, HCl
D)NaBH₄/H₂O
E)PCC

Question 34

Using the molecule shown at the left as your only source of carbon,propose a synthesis of the product shown at the right.

Question 35

What is the product of the following reaction?

A)
B)
C)
D)
E)

Question 36

Explain why the following reaction would be unsuccessful,and suggest a better alternative synthetic route.

Question 37

Which of the following alcohols cannot be oxidized by H₂CrO₄?

A)
B)
C)
D)
E)

Question 38

Show how the following molecule could be synthesized from an α,β-unsaturated ketone or aldehyde.

Question 39

Give an example of an umpolung reaction,and indicate the carbon atom at which polarity reversal is occurring.

Question 40

A student attempted the following synthetic step but did not obtain the desired major product.Explain why the reaction was unsuccessful,and suggest a better synthetic route.

Question 41

Propose a synthetic route to carry out the transformation shown below.

Question 42

Propose a synthesis of the following molecule using benzaldehyde as your only source of carbon.Additional inorganic reagents may be utilized.

Question 43

Predict the major product of the following reaction.

Question 44

Fill in the reagent needed to carry out the following reaction.

Question 45

Fill in the reagent needed to carry out the following reaction.

Question 46

Fill in the missing reagents and intermediates to complete the synthetic scheme below.

Question 47

Design a synthesis of the following molecule using organic precursors with no more than six carbons.Additional inorganic reagents may be utilized.

Question 48

Propose a synthesis of the following molecule using reagents with five or fewer carbon atoms.

Question 49

Propose a synthesis of the product at the right using the given starting material and any other reagents necessary.

Question 50

Propose a synthesis of the following molecule using butyraldehyde as your only source of carbon.