Deck 15: Organic Synthesis 1: Beginning Concepts

Question 1

What is the missing starting material in the following synthetic sequence?

A)
B)
C)
D)
E)

Answer 1

Question 2

Which of the following steps would result in an alteration of the carbon skeleton?

A)
B)
C)
D)
E)

Answer 2

Question 3

Fill in the missing precursor to complete the transform below.

A)CH₃Br
B)CH₃MgBr
C)(CH₃)₃MgBr
D)CH₃CH₂Br
E)CH₃CH₂MgBr

Answer 3

CH₃CH₂MgBr

Question 4

Determine the major product of the following reaction sequence.

A)
B)
C)
D)
E)

Question 5

Which of the following solvents would not be a good choice to use when carrying out the reaction below?

A)DMSO
B)CH₃CH₂CH₂OH
C)CH₃OH
D)DMF
E)Ethyl acetate

Question 6

Determine the final product of the reaction sequence shown below.

A)
B)
C)
D)
E)

Question 7

Which of the following should not be included in a synthetic scheme?

A)Mechanism details
B)Reagents
C)Solvent
D)Reaction temperature
E)Reaction time

Question 8

Which of the following synthetic steps is written correctly and would lead to the product shown?

A)
B)
C)
D)
E)

Question 9

Choose the best precursors that could be used to synthesize the target molecule in the forward direction.

A)
B)
C)
D)
E)

Question 10

Which of the following is appropriate to include in a synthetic step but should not be included in the mechanism for a reaction?

A)Starting materials
B)Mechanism arrows
C)Products
D)Reaction temperature
E)Necessary reagents

Question 11

Determine the missing precursor needed to synthesize the molecule below.

A)
B)
C)
D)
E)

Question 12

Which of the following would not alter the carbon skeleton of the starting material?

A)
B)
C)
D)
E)

Question 13

Which of the following synthetic steps shows a reagent that is written incorrectly?

A)
B)
C)
D)
E)

Question 14

Which of the following synthetic steps would not be classified as a functional group conversion?

A)
B)
C)
D)
E)

Question 15

Which of the following would not be a reasonable precursor of the target shown below?

A)
B)
C)
D)
E)

Question 16

Which of the following transforms would lead to a synthetic trap when carried out in the forward direction?

A)
B)
C)
D)
E)

Question 17

Which of the following transforms would not be a viable synthesis in the forward direction?

A)
B)
C)
D)
E)

Question 18

Determine the missing starting material for the following synthetic step.

A)
B)
C)
D)
E)

Question 19

Choose the best reaction or sequence of reactions to carry out the following synthetic transformation.

A)
B)
C)
D)
E)

Question 20

Which of the following solvents would be the best choice to use when carrying out the reaction below?

A)H₂O
B)CH₃OH
C)Acetic acid
D)CH₃CH₂OH
E)Cyclohexanol

Question 21

Show how the following could be synthesized from two separate alkynes,each with no more than four carbon atoms.

Question 22

Determine the necessary starting material to complete the step below.

A)
B)
C)
D)
E)

Question 23

Fill in the missing starting material needed to complete the following synthetic step.

Question 24

Determine the missing starting material that would exclusively yield the product shown below.

A)
B)
C)
D)
E)

Question 25

Show how to carry out the following synthesis.

Question 26

Briefly explain why the synthetic step shown below is incorrect,and rewrite it so that it is correct.

Question 27

How do the overall percent yields of the linear and convergent syntheses shown below compare?

A)The convergent synthesis has a higher overall percent yield than the linear synthesis.
B)The linear synthesis has a higher overall percent yield than the convergent synthesis.
C)Both synthetic schemes result in the same overall percent yield.
D)It is not possible to determine how yields compare based on the information given.
E)It depends on how many carbons are in each compound.

Question 28

A researcher synthesizes 2-bromo-2-phenylpentane by reacting 2-phenyl-2-tosylpentane with potassium bromide.Write a synthetic step that shows this reaction,and draw the mechanism.

Question 29

Supply the missing reagents necessary to complete the synthetic steps shown below,and indicate whether each step is a functional group conversion or a carbon-carbon bond formation reaction.

Question 30

Determine the overall percent yield for a five-step synthesis in which the yield of each individual step is 90%.

A)90%
B)45%
C)59%
D)81%
E)33%

Question 31

Show how the following could be synthesized from two different alkyl bromides.

Question 32

Supply the missing reagents necessary to complete the following sequence.

Question 33

Fill in the missing reagent to complete the following synthetic step.

Question 34

A student proposes the following synthesis.Explain why this reaction would not work as intended.

Question 35

Propose a way to carry out the synthetic transformation shown below (may require more than one step).

Question 36

Write a synthetic step that shows the following: A researcher subjects 2-bromoheptane to potassium tert-butoxide with tert-butanol as the solvent.The major product of the reaction is 1-heptene.

Question 37

Which of the following would yield the compound shown via an E2 reaction?

A)
B)
C)
D)
E)

Question 38

Draw two possible sets of precursors that could be used to synthesize the target molecule below.

Question 39

Write a synthetic step that shows the following reaction: 3-pentanone was treated first with lithium diisopropylamide.After this reaction was allowed to reach completion,the resulting product was treated with ethyl bromide to yield 4-methyl-3-hexanone as the overall product.

Question 40

Determine the alkyl bromide and alkyne that could be used to synthesize the target molecule below.

Question 41

Determine an appropriate synthetic step that could be used to carry out the transform below in the forward direction.

Question 42

Calculate the overall percent yield of the following synthetic sequence.

Question 43

Show how the following target could be synthesized using only compounds containing three or fewer carbon atoms as the sources of carbon.

Question 44

Two students need to carry out the synthetic step shown below.One plans to use ethanol as the solvent,while the other opts for methanol.Which is the better choice of solvent,and why?

Question 45

Show how the following transform could be carried out in the forward direction.

Question 46

Show how the following synthetic transformation could be carried out.

Question 47

Show how you would carry out the following transformation.

Question 48

Design two different synthetic routes to produce the target compound shown.One route should start with epoxide and the other should start from a diene.

Question 49

Fill in the missing reagents and intermediates in the synthetic sequence below.

Question 50

A student proposes the following synthetic step.Explain the potential error in this proposed step,and suggest a better alternative to carry out the desired synthetic transformation.