1. To which side, if any, would the following equilibrium lie?

H3C

CH

H3C

OH

H3C

CH

H3C

O- Na+ + NaOH+ H2O

A) to the left D) there is no way to tellB) to the right E) this reaction cannot occur at allC) equally to the right and leftAns

2. What would be the name of the following compound?

HO

A) 3-hydroxymethyl-4-methylheptane D) 2-ethyl-3-propyl-1-butanolB) 2-sec-butyl-1-butanol E) 2-(sec-pentyl)-1-butanolC) 2-ethyl-3-methyl-1-hexanolAns:  

3. What would be the expected product(s) of the following reactions?

CH3

Br

C

O

H

?1. Mg, ether

2.

3. H3O+

A)

CH3

OH

B)

OHH3C

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C)CH3HO

D)CH3

HO

E)CH3

H

CH2OH+

Ans

4. What would be the major organic product of the following reaction?

CH2OH

H ? K2Cr2O7

H2SO4, H2O

A)

CH2

B)

CHO

H

C)

CO2H

H

D)

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O

E)

CH3

OH

Ans

5. What would be the expected product(s) of the following reactions?

Br

?1. Mg, ether

2. D2O

A) C6H5OH B) C6H5D C) C6H5OD D) C6H6 E) both A and CAns

6. Which of the following reactions would produce the alcohol shown?

OH

A)

CH3I

1. Mg, ether

2. CH3CH2CH2CH2CHO

3. H3O+

?

B)

Br ?

1. Mg, ether

2. CH3CHO

3. H3O+

C)

CH3CH2CH2CH2 C

O

CH3

NaBH4

CH3OH

?

D) all of theseE) none of theseAns:  

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7. Which of the following would be the least miscible with (= least soluble in) water?A) H3C CH2 CH2 CH2 OH

B)

CH3

H3C CH2 CH OH

C)CH3

H3C CH CH2 OH

D)CH3

CH3

H3C C OH

E) all have equal water solubilityAns:  

8. Which of the following reagents would accomplish the reaction shown?

O OH

?

A) H2SO4, H2O D) HO, H2OB) H2CrO4 E) none of the aboveC) O2 (slow)Ans:  

9. Which of the sequences below would accomplish the following transformation?

CH2OH CH2D?

A)1. HBr

2. NaBD4, CH3OH

B)1. PBr3

2. Mg, ether 3. D2O

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C)D2SO4

D)1. LiAlD4

2. H3O+

E)1. H2SO4

2. D2, catalyst

Ans:  

10. Which of the following five-carbon alcohols would you expect to be the most soluble in water?A) CH3 CH2 CH2 CH2 CH2OH

B)

CH3 CH2 CH2 CH CH3

OH

C)

CH3 CH2 CH CH2 CH3

OH

D)CH3 CH2 CH CH2OH

CH3

E)CH3

CH3 C CH2OH

CH3

Ans:  

11. What reagent(s) would accomplish the following transformation?

CD2OH C

O

D?

A) Pyridinium chlorochromate D) Potassium dichromateB) LiAlD4 then H3O+ E) H2SO4

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C) H2CrO4

Ans:  

12. Which statement about the preparation of Grignard reagents is not true?

RX + Mg RMgX

A) The reaction must be done in an ether solvent.B) The reagent should be protected from air.C) Methyl, primary, secondary, tertiary and aryl halides may be used.D) Rearrangement may accompany Grignard formation.E) The halogen may be chloride, bromide, or iodide.Ans:  

13. Predict the product of the following reaction:

CH3MgBr1)

2) H3O+

?H3C H

O

A)O

B)

OH

C)OCH3

D)OH

E)

CH3

C

H3C

CH3

CH3

Ans:  

14. Grignard reagents are prepared in ether solvents because:A) THF and diethyl ether will dissolve the Mg metal.

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B) Ether solvents stabilize the Grignard reagent by coordination to the organomagnesium.

C) Ether solvents stabilize magnesium metal by forming a covalent bond.D) Ethers have many acidic protons.E) Ether solvents keep water away from the reaction.Ans

17. What is the expected product of the following reaction?

Li

CH3CH2CH2CH2Cl

1. HO- , H2O2. PCC, CH2Cl2

3. , Et2O

4. H3O+

?

A)OH

B)

O

C)

OH

D)

E)O

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Ans:  

18. What is the major product of the following reaction?

HOO

1) CH3CH2MgBr (1 equiv.) / THF

2) H3O+?

A)

OOH

B)

HOOH

C)

HO

D)

HO

E) no net reaction occursAns:  

19. What is the major product of the following reaction?

1) Br2 / light

2) Mg / THF

3) acetone

4) H3O+

CH3CH2CH3 ?

A)

OH

B)

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OH

C)

O

D)O

E)

OHAns:  

20. What is the major product of the following reaction?

OH1) PCC

2) CH3CH2MgBr (1 equiv.)

3) H3O

?

A)

O

B)OH

C)

D)

O

E) no net reaction occursAns:  

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21. What is the major product of the following reaction?

PCC / CH2Cl2OH?

A)OHO

B)OCH3O

C)HO

D)

E) no reaction occursAns:  

22. Ingestion of which of the following toxic alcohols can cause blindness?A) CH3OH D) C6H5OHB) CH3CH2OH E) HOCH2CH2OHC) (CH3)2CHOHAns:  

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23. Which reagents would accomplish the following reaction?

O ODH?

A) 1. LiAlD4

2. D2OB) 1. LiAlD4

2. H2OC) 1. LiAlH4

2. H2OD) 1. LiAlH4

2. D2OE) 1. NaBD4, CH3OH

2. D2OAns:  

24. Which of the following reactions would produce the alcohol shown below?

OH

A)O

?NaBH4

CH3OH

B)

H

O

?1. CH3MgBr

2. H2O

C)

MgBr?

1. CH3CHO

2. H2O

D) all of the aboveE) two of the aboveAns:  

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25. What is the major product of the following reaction?

O

HO

1) PhMgCl (1 equiv.)

2) H2O?

A)

O

HO

B)

HO

Ph

C)

HO

OH

Me

D)

HO

Ph

OH

E)

HO

Ph

Ph

Ans:  

26. What would be the expected organic product of the following reaction?

+H2O

?Li C

H

O

A)

B)

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C

O

C)OH

D)

C

O

O

E)OH

Ans:  

27. Predict the major product of the following reaction:

OPCC / CH2Cl2 ?

A)

O

B)

HOO

C)

OO

D)

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OO

E) no reaction occursAns:  

28. Which alcohol could be prepared by the greatest number of different combinations of Grignard reagents and carbonyl compounds (aldehydes, ketones, and/or esters)? (No multi-step reactions are intended here.)A)

CH3C CH2CH3CH2CH3

OH

B)OH

C)

H3C C CH3H

OH

D)

CH3CH2C CH2CH3CH2CH3

OH

E)

H3C C CHH

OHCH3

CH3

Ans:  

29. What would be the expected product for the following reaction?

C

O

CH3CH2 CH3

1. LiAlD4 ether2. H2O

A)

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C

OD

CH3CH2CH3

D

B)

C

OH

CH3CH2 CH3

D

C)

C

OD

CH3CH2 CH3

H

D) CH3CH2CD2CH3

E)

C

OH

CH3CH2CH3

H

Ans:  

30. Rank the following alcohols in order of decreasing acidity in solution.

CH3OH CH3CH2OH (CH3)2CHOH (CH3)3COH1 2 3 4

A) 1 > 2 > 3 > 4 D) 4 > 3 > 1 > 2B) 2 > 1 > 3 > 4 E) 1 > 3 > 2 > 4C) 4 > 3 > 2 > 1Ans:  

31. Rank the following organic compounds in order of increasing acidity.

OH

CH3CH2OH ClCH2CH2OH CF3CH2OH

12 3 4

A) 1 < 4 < 3 < 2 D) 2 < 3 < 4 < 1B) 1 < 3 < 4 < 2 E) 1 < 4 < 2 < 3C) 2 < 1 < 3 < 4Ans:  

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32. Which of these reagents will best accomplish the transformation below?Br OH

A) NaOH, H2OB)

KOC(CH3)3

HOC(CH3)3C)

O

H3C ONaDMF, 80 °C

1)

2) NaOH, H2O

D)1) LiAlH4, (CH3CH2)2O

2) H3O+, H2O

E) none of the aboveAns:  

33. For this series of alcohols, which one will have an equilibrium that lies the furthest to the right in a basic solution?CH3OH FCH2OH ClCH2OH BrCH2OH

A) CH3OH D) BrCH2OHB) FCH2OH E) All equilibria will be the sameC) ClCH2OHAns:  

34. For the transformations below, what is the structure of the starting material?H OH

CH2CH3H3CH2C

1) LiAlH4, (CH3CH2)2O

2) H3O+, H2O?

A)O

B)

CH2CH3H3CH2C

O

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C)

CH2CH3H3CH2C

O

D)H OH

CH2CH3H3CH2C

E)

O

CH2CH3H3CH2C

O

Ans:  

35. Choose the reagents to make the conversion from I to II.

A) NaH B) LiAlD4 C) NaBH4 D) H3O+ E) all of the aboveAns:  

36. What is the product of the following reaction? Br

1) Mg, Et2O2) D2O

A)OH

B)H

C)

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OEt

D)D

E) none of the aboveAns:  

39. What would be the major organic product expected from the following reaction?

CH2OHPCC

?

(PCC = CrClO3- R3NH+)

A)

CO2H

B)

O

C)

CHO

D)H3C

CH2

OH

OH

E)

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CH2

Ans:  

40. Which of these reactions will give the product shown?

OH

A)MgBr

O+1)

2) H+, H2O

B)O

+ CH3CH2MgBr

2) H+, H2O

1)

C)O

+ CH3MgBr

2) H+, H2O

1)

D) A and B are correct.E) All of the above will give the product.Ans

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41. Identify the reagent that you would use to go from PGE1 to PGE1?

O

HO OH

PGE1

HO OH

HO

PGE1a

?

A) CrO3-2pyridine B) NaH C) NaBH4 D) H2O E) H2SO4

Ans:  

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