360762846-Ch12-Testbank-PART-2 PDF

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Chapter 12 Testbank Klein Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 1.

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

A) B) C) D) E)

I II III IV I and III

Ans: E Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 2.

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

A) B) C) D) E)

HBr Br2/h Br2/ROOR HBr/ROOR h /NBS

Ans: D Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 3.

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

A) B) C) D) E)

HBr Br2/h Br2/ROOR HBr/ROOR h /NBS

Ans: E Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 4.

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

A) B) C) D) E)

HBr Br2/h Br2 HBr/ROOR h /NBS

Ans: C

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 5.

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

A) B) C) D) E)

HBr Br2/H2O Br2 HBr/ROOR h /NBS

Ans: B Chapter 12 Topic: One-Step Syntheses Section: 12.1

Difficulty Level: Easy 6.

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

A) B) C) D) E)

NaOH heat/H2SO4 CH3CO2H NaOEt KOtBu

Ans: B

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 7.

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

A) B) C) D) E)

I II III IV I and III

Ans: C

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 8.

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

A) B) C) D) E)

NaOtBu HBr H2SO4 NaOH NaSH

Ans: D Chapter 12 Topic: One-Step Syntheses Section: 12.1

Difficulty Level: Easy 9.

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

A) B) C) D) E)

NaOtBu HBr H2SO4 NaOH NaSH

Ans: A Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 10.

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

A)

I

B) C) D) E)

II III IV II and IV

Ans: C

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 11.

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

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O 1) Hg(OAc)2, H2O; 2) NaBH4 1) RCO3H; 2) H3O+ H2SO4, H2O 1) O3; 2) DMS

Ans: C Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 12.

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

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O 1) Hg(OAc)2, H2O; 2) NaBH4 1) RCO3H; 2) H3O+ H2SO4, H2O 1) O3; 2) DMS

Ans: A Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 13.

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

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O 1) Hg(OAc)2, H2O; 2) NaBH4 1) RCO3H; 2) H3O+ H2SO4, H2O 1) O3; 2) DMS

Ans: E Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy

14.

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

A) B) C) D) E)

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

Ans: B Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 15.

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

A) B) C) D) E)

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

Ans: D Chapter 12 Topic: One-Step Syntheses

Section: 12.1 Difficulty Level: Easy 16.

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

?? + En

A) B) C) D) E)

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

Ans: C

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 17.

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

??

A) B) C) D) E) Ans: D

1) OsO4; 2) NaHSO3, H2O NaNH2 H2, Pt Na, NH3(l) H2, Lindlar’s catalyst

Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 18.

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

??

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O NaNH2 H2, Pt Na, NH3(l) H2, Lindlar’s catalyst

Ans: E Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 19.

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

A) B) C) D) E)

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

Ans: D Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 20.

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

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O H2SO4, H2O, HgSO4 H2, Pt 1) 9-BBN; 2) H2O2, NaOH 1) O3; 2) DMS

Ans: B Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 21.

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

A) B)

1) OsO4; 2) NaHSO3, H2O H2SO4, H2O, HgSO4

C) D) E)

NaOH xs NaNH2 1) O3; 2) DMS

Ans: D Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 22.

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

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O H2SO4, H2O, HgSO4 NaOH xs NaNH2 1) O3; 2) H2O

Ans: E Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 23.

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

?? n

A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O ROOR, heat NaOH xs NaNH2 1) O3; 2) H2O

Ans: B Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 24.

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

A) B) C) D) E) Ans: E Chapter 12

1) OsO4; 2) NaHSO3, H2O HBr, ROOR NaBr xs NaNH2 HBr

Topic: Functional Group Transformations Section: 12.2 Difficulty Level: Easy 25.

Select the best reagent to convert 4,5-dimethylhex-2-yne to 4,5-dimethylhex-1yne. A) B) C) D) E)

1) OsO4; 2) NaHSO3, H2O HBr, ROOR NaBr 1) xs NaNH2; 2) H3O+ HBr

Ans: D Chapter 12 Topic: Functional Group Transformations Section: 12.2 Difficulty Level: Medium 26.

Select the best reagent to convert 1-bromo-1-methylcyclohexane to 1-bromo-2methylcyclohexane. A) B) C) D) E)

1) KOtBu; 2) HBr 1) NaOEt; 2) HBr 1) NaOEt; 2) HBr, ROOR 1) KOtBu; 2) HBr, ROOR Br2, h

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) B) C) D) E)

1) KOtBu; 2) Hg(OAc)2, H2O; 3) NaBH4 1) TsCl, pyr; 2) KOtBu; 3) BH3-THF; 4) H2O2, NaOH 1) H2SO4, heat; 2) BH3∙THF; 3) H2O2, NaOH 1) TsCl, pyr; 2) NaOH; 3) BH3∙THF; 4) H2O2, NaOH C and D 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?

A) B) C) D) E)

1) KOtBu; 2) HBr 1) NaOEt; 2) HBr, ROOR 1) H2SO4, heat; 2) Br2, h 1) NaOEt; 2) HBr both A and D work

Ans: A

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) B) C) D) E) Ans: B Chapter 12

1) KOtBu; 2) 1-bromopropane 1) NaNH2; 2) 1-bromopropane 1) NaNH2; 2) 2-bromopropane 1) O3; 2) DMS 1) O3; 2) 1-bromopropane

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

A) B) C) D) E)

II

III

I II III IV 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) B) C) D)

Hept-1-en-4-yne Hept-6-en-3-yne Hept-3-en-6-yne Hept-4-en-1-yne

Ans: A Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy

IV

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) B) C) D) E)

2,3-dimethylnon-4-yne 2,2-dimethylpent-1-yne 3,4-dimethylpent-1-yne 4,4-dimethylhept-1-yne 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 = C12H24) with ozone followed by reaction with DMS produces only (CH3)3CCH2CHO. Which of the following could be compound A? A) B) C) D) E)

cis-2,3,7,8-tetramethyloct-4-ene trans-dodec-6-ene 4,4-dimethylpent-1-ene cis-2,2,7,7-tetramethyloct-4-ene 2,2-dimethyldec-4-ene

Ans: D Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 34.

Which reagents will accomplish the following transformation?

A) B) C) D) E)

NaNH2 1) O3; 2) H2O KMnO4 1) BH3∙THF; 2) H2O2, NaOH 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 then washing with water produces only the compounds shown below. Draw a possibility for Compound X that is consistent with these results.

Ans:

Chapter 12 Topic: Reactions that Change the Carbon Skeleton Section: 12.3 Difficulty Level: Easy 36.

Predict the products of the following reaction:

A) B) C)

I, III, and IV II, III, and IV I, III, and V

D) E)

II, IV, and VI 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 product?

1) NaNH2 2) 1-bromopropane 3) NaNH2

??

4) 1-bromopropane 5) ozone 6) 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.

A) B)

1) I; 2) III; 3) IV; 4) V; 5) II 1) VI; 2) IV; 3) IV; 4) VII; 5) V; 6) II

C) D) E)

1) V; 2) II 1) I; 2) IV; 3) VI; 4) V; 5) II 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:

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:

Ans:

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) B) C) D) E)

only the identity of the functional group(s) must change only the carbon skeleton must change only the location of the functional group(s) must change only the identity and location of the functional group(s) must change 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: 1) NaNH2

1) NaNH2

2) MeI

2) H2O 3) H2/Lindlar

Ans: 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:

A) B) C) D) E) F)

Compound 1 = I; Compound 2 = III Compound 1 = II; Compound 2 = III Compound 1 = VI; Compound 2 = IV Compound 1 = II; Compound 2 = IV Compound 1 = II; Compound 2 = V 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?

A) B) C) D) E)

1) 1) 1) 1) 1)

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

1) 1) 1) 1) 1)

Ans: C

Br2; 2) NaOH; 3) HBr Br2, h; 2) H2, Pt H2, Pt; 2) Br2, h NBS, h; 2) H2, Pt HBr, ROOR; 2) NaOH; 3) HBr

Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Difficult 46.

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

1) NBS, h 2) H2, Pt 3) NaCCH 4) xs O 3 5) H2O

Ans: 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-1butanol.

Ans: 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-2butanol.

Ans:

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?

II

I A) B) C) D) E)

III

IV

I II III IV 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-2methyl-1-butene into 2-methyl-2-butene? A) B) C) D) E)

1) 1) 1) 1) 1)

NaOH; 2) H2, Pt H2, Pt; 2) NaOEt H2, Pt; 2) Br2 H2, Ni2B; 2) KOtBu 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 reactions would most effectively transform trans-2-butene into 1butene? 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) B) C) D) E)

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

1 2 3 4 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:

Ans: Alternatively, steps 2-4 could be 2) H2, Lindlar; 3) MCPBA; 4) aq. H2SO4 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:

1) 1 Br2 , h 2) KOtBu 3) HBr, ROOR Ans:

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:

Ans: Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 57.

Propose an efficient method of completing the following transformation:

Ans: Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Medium 58.

Propose an efficient method of completing the following transformation:

Ans: Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 59.

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

A) B) C) D) E) F)

I II III IV I or IV I, III, or IV

Ans: E Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 60.

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

A) B) C) D) E) F)

I II III IV I or II I, II, or IV

Ans: E

Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Easy 61.

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

A) B) C) D) E) F)

I II III IV I or II I, II, or IV

Ans: D Chapter 12 Topic: Retrosynthetic Analysis Section: 12.5 Difficulty Level: Ea...