Chemistry Chapter 12 1 Which sequence of reagents will accomplish the following transformation

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

I II

Br

III

Br

IV

A) I

B) II

C) III

D) IV

E) I and III

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

Br

??

A) HBr

B) Br2/h

C) Br2/ROOR

D) HBr/ROOR

E) h /NBS

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

??

Br

A) HBr

B) Br2/h

C) Br2/ROOR

D) HBr/ROOR

E) h /NBS

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

?? Br

Br

+ En

A) HBr

B) Br2/h

C) Br2

D) HBr/ROOR

E) h /NBS

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

Br

OH

+ En

??

A) HBr

B) Br2/H2O

C) Br2

D) HBr/ROOR

E) h /NBS

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

OH

??

A) NaOH

B) heat/H2SO4

C) CH3CO2H

D) NaOEt

E) KOtBu

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

Chapter 12

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

Br ??

A) NaOtBu

B) HBr

C) H2SO4

D) NaOH

E) NaSH

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

Br ??

A) NaOtBu

B) HBr

C) H2SO4

D) NaOH

E) NaSH

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

Cl

DBU

III III IV

A) I

B) II

C) III

D) IV

E) II and IV

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

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

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

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

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

??

H

O O

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

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

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

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

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

??

+ 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

Chapter 12

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

18. 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

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

??

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

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

??

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

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

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

??

O

OH

+ CO2

A) 1) OsO4; 2) NaHSO3, H2O

B) H2SO4, H2O, HgSO4

C) NaOH

D) xs NaNH2

E) 1) O3; 2) H2O

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

??

n

A) 1) OsO4; 2) NaHSO3, H2O

B) ROOR, heat

C) NaOH

D) xs NaNH2

E) 1) O3; 2) H2O

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

??

Br

A) 1) OsO4; 2) NaHSO3, H2O

B) HBr, ROOR

C) NaBr

D) xs NaNH2

E) HBr

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

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, h

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

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, h

D) 1) NaOEt; 2) HBr

E) both A and D work

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

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

1) NaNH2

2) CH3I

??

III III IV

A) I

B) II

C) III

D) IV

E) II and III

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

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

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

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

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

H

HO O

+OH

O

Compound X 1) O3

2) DMS

3) H2O

(C8H10)H

36. Predict the products of the following reaction:

1) O3

2) DMS

3) H2O

H H

O

C

OHC OH COOH

O

O O

OHC CHO

O

III III IV VVI

A) I, III, and IV

B) II, III, and IV

C) I, III, and V

D) II, IV, and VI

E) III and IV

37. One compound is produced when acetylene is treated with the following reagents.

What is the IUPAC name of this compound?

1) NaNH2

2) 1-bromopropane

3) NaNH2

4) 1-bromopropane

5) ozone

6) water

??

38. Predict a correct sequence of reactants required to complete the following

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

H

O

??

NaNH2

S

H2OBr O3Na/NH3(l) H2/Pt

III III IV VVI 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

39. Propose an efficient synthesis of propanoic acid from acetylene:

40. Propose an efficient synthesis of cyclopentanone from 1-methylcyclopentane:

O

??