Deck 12: Synthesis

Question 1

Provide the major product(s) obtained from the following reaction:

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

Answer 1

III

Question 2

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) 1) RCO₃H; 2) H₃O⁺
D) 1) BH₃∙THF; 2) H₂O₂, NaOH
E) 1) O₃; 2) DMS

Answer 2

1) BH₃∙THF; 2) H₂O₂, NaOH

Question 3

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) 1) RCO₃H; 2) H₃O⁺
D) H₂SO₄, H₂O
E) 1) O₃; 2) DMS

Answer 3

1) O₃; 2) DMS

Question 4

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) 1) RCO₃H; 2) H₃O⁺
D) H₂SO₄, H₂O
E) 1) O₃; 2) DMS

Question 5

Provide the major product(s) for the following transformation:

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

Question 6

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) NaOH
B) heat/H₂SO₄
C) CH₃CO₂H
D) NaOEt
E) KOtBu

Question 7

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) 1) RCO₃H; 2) H₃O⁺
D) H₂SO₄, H₂O
E) 1) O₃; 2) DMS

Question 8

Predict the major product(s) for the following reaction:

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

Question 9

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) H₂, Pt
D) 1) 9-BBN; 2) H₂O₂, NaOH
E) 1) O₃; 2) DMS

Question 10

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) HBr
B) Br₂/h $\nu$
C) Br₂/ROOR
D) HBr/ROOR
E) h $\nu$ /NBS

Question 11

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) HBr
B) Br₂/h $\nu$
C) Br₂/ROOR
D) HBr/ROOR
E) h $\nu$ /NBS

Question 12

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) HBr
B) Br₂/h $\nu$
C) Br₂
D) HBr/ROOR
E) h $\nu$ /NBS

Question 13

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) NaOtBu
B) HBr
C) H₂SO₄
D) NaOH
E) NaSH

Question 14

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) NaOtBu
B) HBr
C) H₂SO₄
D) NaOH
E) NaSH

Question 15

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) NaNH₂
C) H₂, Pt
D) Na, NH₃(l)
E) H₂, Lindlar's catalyst

Question 16

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) NaNH₂
C) H₂, Pt
D) Na, NH₃(l)
E) H₂, Lindlar's catalyst

Question 17

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) H₂, Pt
D) 1) BH₃∙THF; 2) H₂O₂, NaOH
E) 1) O₃; 2) DMS

Question 18

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) HBr
B) Br₂/H₂O
C) Br₂
D) HBr/ROOR
E) h $\nu$ /NBS

Question 19

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) H₂SO₄, H₂O, HgSO₄
C) H₂, Pt
D) 1) 9-BBN; 2) H₂O₂, NaOH
E) 1) O₃; 2) DMS

Question 20

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) 1) Hg(OAc)₂, H₂O; 2) NaBH₄
C) 1) RCO₃H; 2) H₃O⁺
D) 1) BH₃-THF; 2) H₂O₂, NaOH
E) 1) O₃; 2) DMS

Question 21

Which sequence of reagents will accomplish the following transformation?

A) 1) KOtBu; 2) HBr
B) 1) NaOEt; 2) HBr, ROOR
C) 1) H₂SO₄, heat; 2) Br₂, h $\nu$
D) 1) NaOEt; 2) HBr
E) both A and D work

Question 22

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) H₂SO₄, H₂O, HgSO₄
C) NaOH
D) xs NaNH₂
E) 1) O₃; 2) H₂O

Question 23

Propose an efficient synthesis of propanoic acid from acetylene:

Question 24

Which reagents will accomplish the following transformation?

A) NaNH₂
B) 1) O₃; 2) H₂O
C) KMnO₄
D) 1) BH₃∙THF; 2) H₂O₂, NaOH
E) H₂SO₄, H₂O

Question 25

Compound X has molecular formula C₈H₁₀. Reaction of Compound X with excess ozone, followed by reaction with dimethyl sulfide and then washing with water produces only the compounds shown below. Draw a possibility for Compound X that is consistent with these results.

Question 26

Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methyl-1-cyclohexanol to a secondary position?

A) 1) KOtBu; 2) Hg(OAc)₂, H₂O; 3) NaBH₄
B) 1) TsCl, pyr; 2) KOtBu; 3) BH₃-THF; 4) H₂O₂, NaOH
C) 1) H₂SO₄, heat; 2) BH₃∙THF; 3) H₂O₂, NaOH
D) 1) TsCl, pyr; 2) NaOH; 3) BH₃∙THF; 4) H₂O₂, NaOH
E) C and D will both work

Question 27

Which sequence of reagents will accomplish the following transformation?

A) 1) KOtBu; 2) 1-bromopropane
B) 1) NaNH₂; 2) 1-bromopropane
C) 1) NaNH₂; 2) 2-bromopropane
D) 1) O₃; 2) DMS
E) 1) O₃; 2) 1-bromopropane

Question 28

Select the best reagent to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) HBr, ROOR
C) NaBr
D) 1) xs NaNH₂; 2) H₃O⁺
E) HBr

Question 29

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) H₂SO₄, H₂O, HgSO₄
C) NaOH
D) xs NaNH₂
E) 1) O₃; 2) DMS

Question 30

Predict a correct sequence of reactants required to complete the following transformation in which propanal is the only carbon-containing product.

A) 1) I; 2) III; 3) IV; 4) V; 5) II
B) 1) VI; 2) IV; 3) IV; 4) VII; 5) V; 6) II
C) 1) V; 2) II
D) 1) I; 2) IV; 3) VI; 4) V; 5) II
E) none of the above are correct

Question 31

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) HBr, ROOR
C) NaBr
D) xs NaNH₂
E) HBr

Question 32

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

Question 33

Reaction of compound A (molecular formula = C₇H₁₂) with sodium amide followed by reaction with 1-bromobutane produces (CH₃)₂CHCH(CH₃)CC(CH₂)₃CH₃. What is the name of compound A?

A) 2,3-dimethylnon-4-yne
B) 2,2-dimethylpent-1-yne
C) 3,4-dimethylpent-1-yne
D) 4,4-dimethylhept-1-yne
E) 1-heptyne

Question 34

Predict the products of the following reaction:

A) I, III, and IV
B) II, III, and IV
C) I, III, and V
D) II, IV, and VI
E) III and IV

Question 35

Reaction of compound A (molecular formula = C₁₂H₂₄) with ozone followed by reaction with DMS produces only (CH₃)₃CCH₂CHO. Which of the following could be compound A?

A) cis-2,3,7,8-tetramethyloct-4-ene
B) trans-dodec-6-ene
C) 4,4-dimethylpent-1-ene
D) cis-2,2,7,7-tetramethyloct-4-ene
E) 2,2-dimethyldec-4-ene

Question 36

One compound is produced when acetylene is treated with the following reagents. What is the product?

Question 37

Predict the major product(s) for the reaction of pent-1-en-4-yne with sodium amide followed by reaction with bromoethane.

A) Hept-1-en-4-yne
B) Hept-6-en-3-yne
C) Hept-3-en-6-yne
D) Hept-4-en-1-yne

Question 38

For the transformation shown, select the most appropriate reagent(s) to effect the change.

A) 1) OsO₄; 2) NaHSO₃, H₂O
B) ROOR, heat
C) NaOH
D) xs NaNH₂
E) 1) O₃; 2) H₂O

Question 39

Select the best reagent to convert 1-bromo-1-methylcyclohexane to 1-bromo-2-methylcyclohexane.

A) 1) KOtBu; 2) HBr
B) 1) NaOEt; 2) HBr
C) 1) NaOEt; 2) HBr, ROOR
D) 1) KOtBu; 2) HBr, ROOR
E) Br₂, h $\nu$

Question 40

Predict the major product(s) for the following reaction:

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

Question 41

Which of the following sequences efficiently converts 2-methylpropene and sodium acetylide into 3-methylbutanal?

A) 1) HBr; 2) NaCCH; 3) O₃; 4) H₂O
B) 1) HBr; 2) NaCCH; 3) O₃; 4) DMS
C) 1) HBr, ROOR; 2) NaCCH; 3) O₃; 4) H₂O
D) 1) HBr, ROOR; 2) NaCCH; 3) H₂/Ni₂B 4) O₃; 5) DMS
E) 1) NaCCH; 2) H₂/Ni₂B; 3) O₃; 4) DMS

Question 42

Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-butanol.

Question 43

Which of the following provides an efficient method of converting 3-bromo-2-methyl-1-butene into 2-methyl-2-butene?

A) 1) NaOH; 2) H₂, Pt
B) 1) H₂, Pt; 2) NaOEt
C) 1) H₂, Pt; 2) Br₂
D) 1) H₂, Ni₂B; 2) KOtBu
E) 1) H₂, Pt; 2) KOtBu

Question 44

Propose an efficient method of completing the following transformation:

Question 45

What is the minimum number of steps required to convert 2-methylpropane into 1-bromo-2-methyl-2-propanol?

A) 1
B) 2
C) 3
D) 4
E) 5

Question 46

Using retrosynthetic synthesis, determine which compound(s) could lead to the alcohol shown below in a single step:

A) I
B) II
C) III
D) IV
E) I or II
) I, II, or IV

Question 47

Using retrosynthetic analysis, determine which compound(s) could lead to the alkyne shown below in a single step:

A) I
B) II
C) III
D) IV
E) I or II
) I, II, or IV

Question 48

Propose an efficient synthesis of 1-butene from propyne:

Question 49

Propose a strategy to prepare the target as one of the major products:

Question 50

Which order of reactions would most effectively transform trans-2-butene into 1-butene?

A) convert to the dibromoalkane, then to the terminal alkyne, then to the terminal alkene
B) convert to an alcohol, then to a terminal alkyne, finally to the terminal alkene
C) convert to the terminal alkene in one step
D) shorten the chain by two carbons, then add a two-carbon alkene to the end
E) convert to an alkane, then to a terminal alkyne, and finally to a terminal alkene

Question 51

Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-butanol.

Question 52

Which of the following sequences most efficiently converts 3-methyl-1-pentene into 3-bromo-3-methylpentane?

A) 1) Br₂; 2) NaOH; 3) HBr
B) 1) Br₂, h $\nu$ ; 2) H₂, Pt
C) 1) H₂, Pt; 2) Br₂, h $\nu$
D) 1) NBS, h $\nu$ ; 2) H₂, Pt
E) 1) HBr, ROOR; 2) NaOH; 3) HBr

Question 53

Using retrosynthetic synthesis, determine which compound(s) could lead to the alkene shown below in a single step:

A) I
B) II
C) III
D) IV
E) I or IV
F) I, III, or IV

Question 54

Propose an efficient method of completing the following transformation:

Question 55

Propose an efficient method of completing the following transformation:

Question 56

Propose an efficient method of completing the following transformation:

Question 57

Which of the following alkenes cannot be converted into an alkyne by reaction with bromine followed by excess sodium amide and then with water?

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

Question 58

Identify the changes that must occur in transforming cis-2-butene into 2-butanol:

A) only the identity of the functional group(s) must change
B) only the carbon skeleton must change
C) only the location of the functional group(s) must change
D) only the identity and location of the functional group(s) must change
E) both the carbon skeleton and the identity of the functional group(s) must change

Question 59

Propose an efficient method of completing the following transformation:

Question 60

What is the minimum number of steps required to convert 2-methylpropane into 2-methylpropene?

A) 1
B) 2
C) 3
D) 4
E) 5

Question 61

Which of the following effectively produces 4,4-dimethyl-2-pentyne?

A)
B)
C)
D)

Question 62

Devise a method of converting acetylene into the polymer shown below.

Question 63

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkyne (C):

A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = VI and A = VIII

Question 64

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alcohol (C):

A) B = I and A = VI
B) B = VI and A = I
C) B = III and A = VII
D) B = VII and A = IV
E) B = VIII and A = V

Question 65

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the alkene (C):

A) B = I and A = IV
B) B = II and A = VI
C) B = III and A = I
D) B = I and A = VI
E) B = III and A = II

Question 66

Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Question 67

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that can lead to the compound shown (C):

A) B = I and A = VI
B) B = V and A = II
C) B = IV and A = VII
D) B = I and A = III
E) B = VIII and A = V

Question 68

Devise an efficient synthesis of the compound shown below starting with 4-methyl-2-pentanol.

Question 69

Devise a method to complete the following synthesis.

Question 70

Using retrosynthetic analysis, determine which compound(s) could lead to the alkane shown below in a single step:

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

Question 71

Starting with a primary alkyl bromide, which of the following results in an overall increase in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond.
B) substitute bromide with acetylide, then reduce the alkyne to an alkene.
C) substitute bromide with methoxide.
D) eliminate hydrogen bromide to produce an alkene.

Question 72

Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Question 73

Starting with a primary alkyl bromide, which of the following results in an overall decrease in the length of the carbon skeleton by one carbon?

A) substitute bromide with acetylide, then cleave the triple bond.
B) substitute bromide with acetylide, then reduce the alkyne to an alkene.
C) substitute bromide with methoxide.
D) eliminate hydrogen bromide to produce an alkene, then cleave the double bond.

Question 74

Devise a method to complete the following synthesis.

Question 75

Devise a method of converting ethylene into PVC (polyvinyl chloride).

Question 76

Devise a method of converting methylcyclobutane into cyclopentene.

Question 77

Devise a method of converting trans-2-methyl-3-hexene into 5-methylhexanal.

Question 78

Using retrosynthetic analysis, determine which compound(s) could lead to the bromoalkene shown below in a single step:

A) I or III
B) I or IV
C) I
D) II
E) III
F) IV

Question 79

Show that you understand the concept of retrosynthetic analysis by working backwards two steps in the synthesis below. Identify possible combinations of A and B that could lead to the alkyl halide (C):

A) B = I and A = VIII
B) B = VI and A = I
C) B = III and A = VII
D) B = IV and A = VII
E) B = V and A = VIII

Question 80

Devise a method of converting trans-2-methyl-3-hexene into 4-methylpentanoic acid.