Question 1

Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

Accepted Answer

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Question 2

Predict the reagent(s) required to complete the following transformation: 4;2) NaHSO3,H2O B) 1) Hg(OAc) 2,H2O;2) NaBH4 C) 1) RCO3H;2) H3O+ D) H2SO4,H2O E) 1) O3;2) DMS" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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) DMSF) B) and D)
G) D) and E)

Question 3

One compound is produced when acetylene is treated with the following reagents.What is the IUPAC name of this compound?

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Question 4

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?

Accepted Answer

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-heptyneF) A) and B)
G) A) and D)

Question 5

Propose a strategy to carry out the following transformation:

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Question 6

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

Accepted Answer

A)  I
B)  II
C)  III
D)  IV
E)  III and IVF) D) and E)
G) None of the above

Question 7

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

Accepted Answer

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 changeF) None of the above
G) All of the above

Question 8

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

Accepted Answer

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

Question 9

Propose an efficient method of completing the following transformation:

Accepted Answer

The answer of Propose an efficient method of completing the...

Question 10

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

Accepted Answer

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 correctF) C) and E)
G) All of the above

Question 11

Which sequence of reagents will accomplish the following transformation? 2SO4,heat;2) Br2,h 
u  D) 1) NaOEt;2) HBr E) both A and D work " class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  1) KOtBu;2) HBr
B)  1) NaOEt;2) HBr,ROOR
C)  1) H2SO4,heat;2) Br2,h ν
uν 
D)  1) NaOEt;2) HBr
E)  both A and D work F) A) and B)
G) A) and C)

Question 12

Propose an efficient synthesis of 1-butene from propyne:

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Question 13

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

Accepted Answer

Question 14

Predict the reagent(s) required to complete the following transformation: 4;2) NaHSO3,H2O B) HBr,ROOR C) NaBr D) xs NaNH2 E) HBr" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 15

Predict the reagent(s) required to complete the following transformation: 2SO4 D) NaOH E) NaSH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  NaOtBu
B)  HBr
C)  H2SO4
D)  NaOH
E)  NaSHF) A) and B)
G) A) and E)

Question 16

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

Accepted Answer

A)  Hept-1-en-4-yne
B)  Hept-6-en-3-yne
C)  Hept-3-en-6-yne
D)  Hept-4-en-1-yneE) All of the above
F) None of the above

Question 17

Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

Accepted Answer

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

Question 18

Provide the reagent(s) required to complete the following transformation: 2SO4 C) CH3CO2H D) NaOEt E) KOtBu" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

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

Question 19

Predict the reagent(s) required to complete the following transformation: 2SO4 D) NaOH E) NaSH" class="answers-bank-image d-inline" rel="preload" >

Accepted Answer

A)  NaOtBu
B)  HBr
C)  H2SO4
D)  NaOH
E)  NaSHF) All of the above
G) C) and E)

Question 20

Propose an efficient method of completing the following transformation:

Accepted Answer

The answer of Propose an efficient method of completing the...

Exam 12: Synthesis

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

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Predict the reagent(s) required to complete the following transformation:

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Predict the reagent(s) required to complete the following transformation:

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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?

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Propose a strategy to carry out the following transformation:

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Predict the reagent(s) required to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1-yne.

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Which sequence of reagents will accomplish the following transformation?

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Provide the reagent(s) required to complete the following transformation:

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Predict the reagent(s) required to complete the following transformation:

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Predict the reagent(s) required to complete the following transformation:

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Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

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

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Propose an efficient method of completing the following transformation:

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Propose an efficient method of completing the following transformation:

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

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One compound is produced when acetylene is treated with the following reagents.What is the IUPAC name of this compound?

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

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

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Propose an efficient synthesis of 1-butene from propyne:

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

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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?

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Which sequence of reagents will accomplish the following transformation? $Which sequence of reagents will accomplish the following transformation? A) 1) KOtBu;2) HBr B) 1) NaOEt;2) HBr,ROOR C) 1) H<sub>2</sub>SO<sub>4</sub>,heat;2) Br<sub>2</sub>,h \nu D) 1) NaOEt;2) HBr E) both A and D work$

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

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