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

H3C CH O Na H3C A) to the left B) to the right C) equally to the right and left Ans
+

H3C + H2O H3C D) E) there is no way to tell this reaction cannot occur at all CH OH + NaOH

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

A) 3-hydroxymethyl-4-methylheptane B) 2-sec-butyl-1-butanol C) 2-ethyl-3-methyl-1-hexanol Ans:

D) E)

2-ethyl-3-propyl-1-butanol 2-(sec-pentyl)-1-butanol

3. What would be the expected product(s) of the following reactions? CH3 Br 1. Mg, ether O 2. 3. H3O+ A) OH CH3 C H

B)

H3C OH
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C)
HO CH3

D) CH3 HO E) CH3 H
+

CH2OH

Ans 4. What would be the major organic product of the following reaction? K2Cr2O7
H CH2OH

H2SO4, H2O

A)

CH2

B)
H CHO

C)
H CO2H

D)

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E)
CH3 OH

Ans 5. What would be the expected product(s) of the following reactions? 1. Mg, ether
Br ?

2. D2O B) C6H5D

A) C6H5OH Ans

C) C6H5OD

D) C6H6

E) both A and C

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

A) 1. Mg, ether CH3I 2. CH3CH2CH2CH2CHO 3. H3O+ B) 1. Mg, ether Br 2. CH3CHO 3. H3O+ C) CH3CH2CH2CH2 D) all of these E) none of these Ans: O C CH3 NaBH4 CH3OH ? ? ?

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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)
H3C CH2 CH OH CH3

C)
CH3 H3C CH CH2 OH CH3 H3C C CH3 OH

D)

E) all have equal water solubility Ans: 8. Which of the following reagents would accomplish the reaction shown? O ? OH

A) H2SO4, H2O B) H2CrO4 C) O2 (slow) Ans:

D) E)

HO , H2O none of the above

9. Which of the sequences below would accomplish the following transformation? CH2OH A) 1. HBr 2. NaBD4, CH3OH B) 1. PBr3 2. Mg, ether 3. D2O
?

CH2D

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C) D2SO4 D) 1. LiAlD 4 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)
OH CH3 CH2 CH2 CH CH3 OH CH3 CH2 CH CH2 CH3

C)

D)
CH3 CH2 CH CH2OH CH3

E)
CH3 CH3 C CH3 CH2OH

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

A) B)

Pyridinium chlorochromate LiAlD4 then H3O+

D) E)

Potassium dichromate H2SO4

C) H2CrO4 Ans: 12. Which statement about the preparation of Grignard reagents is not true? RX + Mg A) B) C) D) E) Ans: RMgX

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

13. Predict the product of the following reaction:

1) CH3MgBr A)
O

H3C

2) H3O+

B)
OH

C)
OCH3

D)
OH

E)
H3C CH3 C 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) C) D) E) Ans

Ether solvents stabilize the Grignard reagent by coordination to the organomagnesium. Ether solvents stabilize magnesium metal by forming a covalent bond. Ethers have many acidic protons. Ether solvents keep water away from the reaction.

17. What is the expected product of the following reaction? 1. HO- , H2O 2. PCC, CH2Cl2 3. 4. H3O+ A)
OH

CH3CH2CH2CH2Cl

Li , Et2O

B) O C)

OH

D)

E)
O

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Ans: 18. What is the major product of the following reaction? O HO

A) O B) HO C) HO D) HO E) no net reaction occurs Ans: 19. What is the major product of the following reaction? 1) Br2 / light CH3CH2CH3 2) Mg / THF 3) acetone 4) H3O+ A)
OH

OH

OH

B)

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OH C) O D)
O

E)

OH

Ans: 20. What is the major product of the following reaction? OH 1) PCC 2) CH3CH2MgBr (1 equiv.) 3) H3O ?

A)
O

B) OH C)

D) O E) no net reaction occurs Ans:

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21. What is the major product of the following reaction? OH PCC / CH2Cl2

A) O OH

B) O OCH3

C) O H

D)

E) no reaction occurs Ans: 22. Ingestion of which of the following toxic alcohols can cause blindness? A) CH3OH D) C6H5OH B) CH3CH2OH E) HOCH2CH2OH C) (CH3)2CHOH Ans:

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23. Which reagents would accomplish the following reaction? O

H OD

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

1. LiAlD4 2. D2O 1. LiAlD4 2. H2O 1. LiAlH4 2. H2O 1. LiAlH4 2. D2O 1. NaBD4, CH3OH 2. D2O

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

A) O
NaBH4 CH3OH ?

B) O H C) MgBr 1. CH 3CHO
2. H 2O ? 1. CH3MgBr 2. H2O ?

D) all of the above E) two of the above Ans:

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25. What is the major product of the following reaction? O HO A)

1) PhMgCl (1 equiv.) ? 2) H2O

B) Ph HO C) OH HO D) Ph HO E) Ph HO Ans: 26. What would be the expected organic product of the following reaction?
O Li C

Me

OH

Ph

+ A)

H2O

B)

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O C

C)
OH

D)
O C O

E)
OH

Ans: 27. Predict the major product of the following reaction: O A)

B)
O HO

C)
O O

D)

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O O E) no reaction occurs Ans: 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) OH CH3 C CH2CH3 CH2CH3 B) OH C) OH H3C C CH3 H D) OH CH3CH2 C CH2CH3 CH2CH3 E) OH H3C C CH H CH Ans: 29. What would be the expected product for the following reaction? O CH3CH2 A) C CH 3 1. LiAlD4 ether 2. H 2O CH3

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OD CH 3CH 2 B) OH CH3CH2 C) OD CH 3 CH3CH2CD2CH3 OH CH3CH2 Ans: 30. Rank the following alcohols in order of decreasing acidity in solution. CH3OH
1

C D CH 3

C D CH3

CH 3CH 2

C H

D) E)

C H CH3

CH3CH 2OH
2

(CH3)2CHOH
3

(CH3)3COH
4

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

D) E)

4>3>1>2 1>3>2>4

31. Rank the following organic compounds in order of increasing acidity. OH CH3CH2OH
2 1

ClCH2CH2OH
3

CF3CH2OH
4

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

D) E)

2<3<4<1 1<4<2<3

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

A) B)

NaOH, H2O
KOC(CH3)3 HOC(CH3)3

C)
O 1) H C ONa 3 DMF, 80 C 2) NaOH, H2O

D)
1) LiAlH4, (CH3CH2)2O 2) H3O+, H2O

E) none of the above Ans: 33. For this series of alcohols, which one will have an equilibrium that lies the furthest to the right in a basic solution?
CH 3OH FCH 2OH ClCH 2OH BrCH 2OH

A) CH3OH B) FCH2OH C) ClCH2OH Ans:

D) E)

BrCH2OH All equilibria will be the same

34. For the transformations below, what is the structure of the starting material?
H 1) LiAlH4, (CH3CH2)2O OH

?
A)
O

2) H3O+, H2O H3CH2C

CH2CH3

B)
O

H3CH2C

CH2CH3

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C)
O H3CH2C CH2CH3

D)
H OH

H3CH2C

CH2CH3

E)
O O H3CH2C CH2CH3

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

A) NaH Ans:

B) LiAlD4

C) NaBH4

D) H3O+ E) all of the above

36. What is the product of the following reaction? Br 1) Mg, Et2O 2) D2O A) OH

B)
H

C)

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OEt

D)
D

E) none of the above Ans:

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

CH2OH

(PCC = CrClO3- R3NH+) A) CO2H B) O C) CHO D) H3C OH CH2 OH E)

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CH2

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

A)
MgBr 1) + O

2) H+, H2O

B)
O 1) + CH3CH2MgBr

2) H+, H2O

C)
O 1) + CH3MgBr

2) H+, H2O

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? HO O

? HO

HO

OH

OH

PGE1a PGE1 A) CrO3-2pyridine B) NaH C) NaBH4 D) H2O E) H2SO4 Ans:

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