Deck 11: Synthesis

Question 1

Select the best reagents for the reaction below.

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

Answer 1

HBr/ROOR

Question 2

Select the best reagents for the reaction below.

A) HBr
B) Br₂/H₂O
C) Br₂, CCl₄
D) HBr/ROOR
E) h $\upsilon$ /NBS

Answer 2

Br₂/H₂O

Question 3

Select the best reagents for the reaction below.

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 3

1. Hg(OAc)₂, H₂O; 2. NaBH₄

Question 4

Select the best reagents for the reaction below.

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 5

Select the best reagents for the reaction below.

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

Question 6

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

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

Question 7

Select the best reagents for the reaction below.

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

Question 8

Select the best reagents for the reaction below.

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 9

Select the best reagents for the reaction below.

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

Question 10

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

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

Question 11

Select the best reagents for the reaction below.

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

Question 12

Select the best reagents for the reaction below.

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 13

Select the best reagents for the reaction below.

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 14

Select the best reagents for the reaction below.

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 15

Select the best reagents for the reaction below.

A) HBr
B) Br₂/h $\upsilon$
C) Br₂, CCl₄
D) HBr/ROOR
E) h $\upsilon$ /NBS

Question 16

Provide the major product(s) for the following synthesis.

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

Question 17

Select the best reagents for the reaction below.

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 18

Select the best reagents for the reaction below.

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

Question 19

Select the best reagents for the reaction below.

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

Question 20

Select the best reagents for the reaction below.

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 21

Propose a synthesis of propanoic acid from acetylene.

Question 22

Select the best reagents for the reaction below.

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

Question 23

Which sequence of reagents will accomplish the following synthesis?

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 24

Select the best reagents for the reaction below.

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

Question 25

Select the best reagents for the reaction below.

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

Question 26

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

A) 1. OsO₄; 2. NaHSO₃, H₂O
B) HBr, ROOR
C) NaBr
D) Na, NH₃
E) HBr

Question 27

Reaction of compound A (molecular formula = C₇H₁₂) with sodium amide, followed by reaction with 1-bromobutane produces a compound with a structure of (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 28

Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methylcyclohexanol 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 29

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
E) hept-2-en-4-yne

Question 30

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 31

Propose a synthesis of cyclopentanone from 1-methylcyclopentane.

Question 32

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

Question 33

Which sequence of reagents will accomplish the following synthesis?

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

Question 34

Predict a correct sequence of reactants required to complete the following synthesis in which propanal is the only carbon-containing product. NaNH₂ CH₃SCH₃ H₂O CH₃CH₂Br O₃ Na/NH₃(l) H₂/Pt I II III IV V VI VII

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 35

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 $\upsilon$

Question 36

Select the best reagents for the reaction below.

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

Question 37

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

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

Question 38

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 39

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 40

Select the best reagents for the reaction below.

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

Question 41

Propose a synthetic route to convert 3-methyl-2-butanol into 3-methyl-1-butanol.

Question 42

Propose a synthesis to produce the following answer as one of the major products.

Question 43

Identify the changes that must occur in converting 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 44

Propose a synthetic route for the following equation.

Question 45

Propose a synthetic route for the following reaction.

Question 46

Which of the following sequences 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 47

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

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

Question 48

Using retrosynthetic synthesis, 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

Question 49

Propose a synthetic route for the following reaction.

Question 50

The following sequence of reactions transforms acetylene into a compound with an altered carbon skeleton (compound 1), and from that into a compound in which the functional group has been changed (compound 2). Identify compounds 1 and 2.

A) Compound 1 = I; Compound 2 = III
B) Compound 1 = II; Compound 2 = III
C) Compound 1 = VI; Compound 2 = IV
D) Compound 1 = II; Compound 2 = IV
E) Compound 1 = II; Compound 2 = V

Question 51

Propose a synthetic route for the following reaction.

Question 52

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 53

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 54

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

Question 55

Propose a synthesis of 1-butene from propyne.

Question 56

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

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

Question 57

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

A) convert to the gem-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 58

Which of the following provides a synthetic route to convert 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 59

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

Question 60

Propose a synthetic route to convert 3-methyl-1-butanol into 3-methyl-2-butanol.

Question 61

Using retrosynthetic synthesis, 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 62

Devise a synthetic route to convert ethylene into PVC (polyvinyl chloride).

Question 63

Devise a method of converting 4-methyl-1-pentene into 3-methylbutanoic acid.

Question 64

Devise a synthetic route of the compound shown below starting with 4-methyl-2-pentanol.

Question 65

Perform a 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 66

Perform a 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 67

Devise a synthetic route to convert methylcyclobutane into cyclopentene.

Question 68

Perform a 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 = II
E) B = VIII and A = V

Question 69

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 70

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

Question 71

Devise a synthetic route for the following equation.

Question 72

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

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

Question 73

Perform a 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 74

Devise a synthetic route of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Question 75

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 76

Devise a synthetic route of the diol shown below starting with 1,1,3,3-tetramethyl-2-ethylcyclohexane.

Question 77

Devise a synthetic route for the following equation.

Question 78

Using retrosynthetic synthesis, 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

Question 79

Perform a 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 80

Devise a synthetic route to convert 5-methyl-1-hexene into 5-methylhexanal.