Chapter 12 Testbank (Klein)- Draft 3 Chapter 12 Topic: One ......Chapter 12 Testbank (Klein)- Draft...

Chapter 12 Testbank (Klein)- Draft 3 Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 1. Predict the major product(s) for the following reaction:

HBr

Br

Br

I II

Br

III

Br

IV

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

Ans: E

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 2. Provide the reagent(s) required to complete the following transformation:

Br

??

A) HBr

B) Br2/hν C) Br2/ROOR D) HBr/ROOR E) hν /NBS

Ans: D


??Br

A) HBr B) Br2/hν C) Br2/ROOR D) HBr/ROOR E) hν /NBS

Ans: E


?? Br

Br

+ En

A) HBr

B) Br2/hν C) Br2 D) HBr/ROOR E) hν /NBS

Ans: C


Br

OH

+ En??

A) HBr B) Br2/H2O C) Br2 D) HBr/ROOR E) hν /NBS

Ans: B


OH

??

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

Ans: B

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 7. Predict the major product(s) for the following transformation:

Br

NaSH

SH

Br HS HS

I II III IV

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

Ans: C

Chapter 12

Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 8. Predict the reagent(s) required to complete the following transformation:

Br??

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

Ans: D

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 9. Predict the reagent(s) required to complete the following transformation:

Br??

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

Ans: A

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 10. Predict the major product(s) obtained from the following reaction:

ClDBU

DBU

I II III IV

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

Ans: C


OH

OH + En??

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

Ans: C


OH

OH

+ En??


Ans: A

Chapter 12 Topic: One-Step Syntheses Section: 12.1

Difficulty Level: Easy 13. Predict the reagent(s) required to complete the following transformation:

??

H

O O


Ans: E


OH + En??

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

Ans: B

Chapter 12 Topic: One-Step Syntheses

Section: 12.1 Difficulty Level: Easy 15. Predict the reagent(s) required to complete the following transformation:

+ En??

OH

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

Ans: D


??+ En

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

Ans: C

Chapter 12

Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 17. Predict the reagent(s) required to complete the following transformation:

??

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

Ans: D


??

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

Ans: E



??

H

O

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

Ans: D


??

O

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

Ans: B

Chapter 12 Topic: One-Step Syntheses Section: 12.1

Difficulty Level: Easy 21. Predict the reagent(s) required to complete the following transformation:

Br Br

?? Na

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

Ans: D


??O

OH

+ CO2

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

Ans: E



??

n

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

Ans: B


??Br

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

Ans: E

Chapter 12 Topic: Functional Group Transformations Section: 12.2 Difficulty Level: Easy 25. Predict the reagent(s) required 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

Ans: D

Chapter 12 Topic: Functional Group Transformations Section: 12.2 Difficulty Level: Medium 26. Predict the reagent(s) required 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, hν

Ans: C

Chapter 12 Topic: Functional Group Transformations Section: 12.2 Difficulty Level: Medium 27. 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 F) A and B will both work

Ans: E

Chapter 12 Topic: Functional Group Transformations Section: 12.2 Difficulty Level: Medium 28. Which sequence of reagents will accomplish the following transformation?

Br?? Br

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

Ans: E

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 29. 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

Ans: B

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 30. Predict the major product(s) for the following reaction:

1) NaNH2

2) CH3I??

I II III IV

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

Ans: C

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 31. 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

Ans: A

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 32. 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

Ans: C

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Medium 33. Reaction of compound A (molecular formula = C12H22) 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

Ans: D

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 34. Predict the reagent(s) required to complete the following reaction:

O

HO

O

OH??

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

Ans: B

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Medium 35. 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.

O

O

H

HO O

+OH

O

Compound X 1) O3

2) DMS3) H2O

(C8H10) H

Ans:

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 36. Predict the products of the following reaction:

1) O3

2) DMS3) H2O

H H

O

OC

OHC OH COOH

OO O

OHC CHO

O

I II III IV V VI

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

Ans: B

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Medium 37. One compound is produced when acetylene is treated with the following reagents.

What is the IUPAC name of this compound?

1) NaNH22) 1-bromopropane3) NaNH2

4) 1-bromopropane5) ozone6) water

??

Ans: butanoic acid

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Medium 38. Predict a correct sequence of reactants required to complete the following

transformation in which propanal is the only carbon-containing product.

H

O??

NaNH2S

H2O BrO3 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

Ans: D

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Medium 39. Propose an efficient synthesis of propanoic acid from acetylene:

Ans:

1) NaNH2

2) CH3CH2Br

1) O3

2) H2OCO2H

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 40. Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

O??

Ans:

Br2, hν

Br

KOtBu 1) ozone

2) DMS

O

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy 41. 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

Ans: A Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 42. Propose an efficient synthesis of 1-butene from propyne:

Ans:

1) NaNH2

2) MeI

1) NaNH2

2) H2O3) H2/Lindlar

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 43. 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:

1) NaNH2

2) bromoethane1

1) H2, Ni2B

2) BH3-THF3) H2O2, NaOH

OHOH

OH

OH

2

I II III IV

V VI VII VIII

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 F) Compound 1 = VII; Compound 2 = VIII

Ans: D

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 44. Which of the following sequences efficiently converts 2-methylpropene and

sodium acetylide into 3-methylbutanal?

H

O

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 3) O3; 4) DMS E) 1) NaCCH; 2) H2/Ni2B; 3) O3; 4) DMS

Ans: D

Chapter 12 Topic: How to Approach a Synthesis Problem

Section: 12.4 Difficulty Level: Medium 45. Which of the following sequences most efficiently converts 3-methyl-1-pentene

into 3-bromo-3-methylpentane?

A) 1) HBr; 2) NaOH; 3) HBr B) 1) Br2, hν; 2) H2, Pt C) 1) H2, Pt; 2) Br2, hν D) 1) NBS, hν; 2) H2, Pt E) 1) HBr, ROOR; 2) NaOH; 3) HBr

Ans: C

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Difficult 46. Propose a strategy to carry out the following transformation:

?? O

OH

Ans:

1) NBS, hν2) H2, Pt3) NaCCH

4) xs O35) H2O

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 47. Propose an efficient method of converting 3-methyl-2-butanol into 3-methyl-1-

butanol.

Ans:

OH 1) TsCl, pyr2) KOtBu

3) BH3-THF4) H2O2, NaOH

OH

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 48. Propose an efficient method of converting 3-methyl-1-butanol into 3-methyl-2-

butanol.

Ans:

OH1) H2SO4, heat2) Hg(OAc)2, H2O

3) NaBH4OH

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy 49. Which of the following alkenes cannot be converted into an alkyne by reaction

with bromine followed by excess sodium amide and then with water?

I II III IV

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

Ans: D

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 50. 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) xs NaNH2 D) 1) H2, Ni2B; 2) KOtBu E) 1) H2, Pt; 2) KOtBu

Ans: B

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy 51. Which order of alterations 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

Ans: A

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy 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

Ans: B

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy 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

Ans: C

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 54. Propose an efficient method of completing the following transformation:

Br

??

HO

OH+ En

Ans: Br

1) NaCCCH32) Na/NH3(l)3) OsO4

4) NaHSO3, H2O

Chapter 12 Topic: How to Approach a Synthesis Problem

Section: 12.4 Difficulty Level: Medium 55. Propose an efficient method of completing the following transformation:

??

S

Ans:

1) 1 Br2, hν2) KOtBu3) HBr, ROOR

4) NaSMe Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 56. Propose an efficient method of completing the following transformation:

Br??

S

Ans:

Br S1) NaOEt2) NBS, hν

3) NaSMe


OH

O

??

Ans:

OH

O1) Br22) xs NaNH23) H2O

4) O35) H2O


Br

CHO??

Ans:

Br

CHO

1) NaCCH2) 9-BBN

3) H2O2, NaOH

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 59. Demonstrate your understanding of retrosynthetic synthesis and determine which

compound(s) could lead immediately to the alkene shown below:

??

BrI II III IV

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

Ans: E Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 60. Using retrosynthetic synthesis, determine which compound(s) could lead

immediately to the alcohol shown below:

OH

??

I II III IV

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

Ans: E

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 61. Using retrosynthetic synthesis, determine which compound(s) could lead

immediately to the alkyne shown below:

??

Br

I II III IVBr Br

Br

Br

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

Ans: D Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 62. Using the concept of retrosynthetic synthesis, determine which compound(s)

could lead immediately to the alkane shown below:

??

I II III IVBr OH

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

Ans: B Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 63. Using the concept of retrosynthetic synthesis, determine which compound(s)

could lead immediately to the bromoalkene shown below:

Br ??

Br Br

OH

I II III IV

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

Ans: C Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 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 could lead to the alkyl halide (C):

Br

B A

C

Br

I II III IV

V VI VII VIII

OH

Br

Cl

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 = I and A = III F) B = V and A = VIII

Ans: A, D, and E Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 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 alkyne (C):

B A

C

Br

I II III IV

V VI VII VIII

OH

Br

ClBr

BrBr

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 = I and A = III F) B = VI and A = VIII

Ans: B Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 66. 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):

B A

C

Br

I II III IV

V VI VII VIII

Br

ClBr

BrBr

OH

Br

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 = I and A = III F) B = VIII and A = V

Ans: D and F Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 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):

B A

I II III IV

V VI VII VIIICl

BrBr

OH

OH

+ En

OH

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

Ans: C Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 68. 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):

B A

Br

I II III

V VI VII

Br HO

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

Ans: B and E Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 69. Devise a method of converting methylcyclobutane into cyclopentene.

??

1) Br2, hν2) KOtBu3) BH3-THF

4) H2O2, NaOH5) H2SO4, heat

Ans:

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 70. Devise a method of converting ethylene into PVC (polyvinyl chloride).

Ans:

1) Br22) xs NaNH23) H2O

4) 1 eq HCl5) ROOR, heat Cl

n

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 71. Devise a method of converting acetylene into the polymer shown below.

Cl

n

1) NaNH22) CH3Br3) HCl

4) ROOR, heatAns:

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 72. Devise a method of converting trans-2-methyl-3-hexene into 5-methylhexanal.

Ans:


4) disiamylborane5) H2O2, NaOH

CHO

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 73. Devise a method of converting trans-2-methyl-3-hexene into 4-methylpentanoic

acid.

Ans:


4) ozone5) H2O

COOH

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 74. Which of the following effectively produces 4,4-dimethyl-2-pentyne?

A) Br+ NaCCCH3

B) + CH3Br

C)

Br Br

+ 2 NaNH2

D) Br+ 1 NaNH2

Ans: B and C

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Difficult 75. Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-

tetramethyl-2-ethylcyclohexane.

OH

OH

+ En

Ans:

1) Br2, hν2) KOtBu3) HBr, ROOR

4) KOtBu5) Br26) xs NaNH27) CH3Br8) H2, Lindlar9) OsO410) NaHSO3, H2O

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Difficult 76. Devise an efficient synthesis of the diol shown below starting with 1,1,3,3-

tetramethyl-2-ethylcyclohexane.

OH

OH

+ En

Ans:

1) Br2, hν2) KOtBu3) HBr, ROOR

4) KOtBu5) Br26) xs NaNH27) CH3Br8) H2, Lindlar9) RCO3H10) H3O+

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Difficult 77. Devise an efficient synthesis of the compound shown below starting with 4-

methyl-2-pentanol.

O

O

OH

OH

Ans:

1) TsCl, pyr2) KOtBu3) HBr/ROOR

4)

ONa

O

Chapter 12

Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 78. To add one carbon directly to the end of a primary alkyl bromide, one could:

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.

Ans: A

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 79. To remove one carbon from the end of a primary alkyl bromide, one could:

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.

Ans: D

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 80. Devise a method to complete the following synthesis.

Br

OH

+

OH

Br

1) NaOEt2) BH3-THF

3) H2O2, NaOH

OH

+

OH

Ans:

??


Oacetylene

1) NaNH22) CH3Br3) NaNH24) CH3Br

5) H2, Lindlar's catalyst6) RCO3H

Ans:


O

acetylene

1) NaNH22) CH3Br3) NaNH24) CH3Br

5) Na, NH3(l)6) RCO3H

Ans:

+ En


N N

N N

1) NBS, hν2) HBr, ROOR

3) 2 NaCNAns:

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Difficult 84. Devise a method to prepare 1,7-heptanediol from propene.

1) NBS, hν2) HBr, ROOR

3) 2 NaCCH4) H2, Lindlar5) BH3-THF6) H2O2, NaOH

Ans:HO OH

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 85. Devise a method to prepare 1,3-dibromopropanol from propene.

1) NBS, hν2) Br2, H2O

Ans: Br Br

OH

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 86. Devise a method to prepare 3-bromo-1-propanol from propene.

1) NBS, hν2) BH3-THF

3) H2O2, NaOHAns: Br OH


1) NBS, hν2) KCN

Ans:

N

N

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Medium 88. Devise a synthesis to lengthen the legs of “Ralph” as requested below.

Ans:

1) NBS, hν2) HBr, ROOR3) 2 NaCCH4) H2, Pt

Chapter 12 Testbank (Klein)- Draft 3 Chapter 12 Topic: One ......Chapter 12 Testbank (Klein)- Draft...

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