Deck 8: Hydroxy of Functional Group: Alcohols: Properties,preparation,and Strategy of Synthesis

Question 1

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

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

Answer 1

C₆H₅D

Question 2

Which is the correct structure for the following IUPAC name?

A)

B)

C)

D)

E)

Answer 2

Question 3

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Answer 3

Question 4

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

A)

B)

C)

D)

E)

Question 5

What is the major product of the following reaction?

A)

B)

C)

D)

E) No reaction occurs.

Question 6

What would be the name of the following compound?

A) 3-hydroxymethyl-4-methylheptane
B) 2-sec-butyl-1-butanol
C) 2-ethyl-3-methyl-1-hexanol
D) 2-ethyl-3-propyl-1-butanol
E) 2-(sec-pentyl)-1-butanol

Question 7

What is the major product of the following reaction?

A)

B)

C)

D)

E) No net reaction occurs.

Question 8

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 9

What is the major product of the following reaction?

A)

B)

C)

D)

E) No net reaction occurs.

Question 10

Grignard reagents are prepared in ether solvents because:

A) THF and diethyl ether will dissolve the Mg metal.
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.

Question 11

Which of the following would be the least miscible with (= least soluble in)water?

A)

B)

C)

D)

E) All have equal water solubility.

Question 12

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

A)

B)

C)

D)

E)

Question 13

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

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.

Question 14

Predict the product of the following reaction:

A)

B)

C)

D)

E)

Question 15

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

A) to the left
B) to the right
C) equally to the right and left
D) There is no way to tell.
E) This reaction cannot occur at all.

Question 16

Which of the following five-carbon alcohols would you expect to be the most soluble in water?

A)

B)

C)

D)

E)

Question 17

What is the expected product of the following reaction?

A)

B)

C)

D)

E)

Question 18

Which of the following reactions would produce the alcohol shown?

A)

B)

C)

D) All of these.
E) None of these.

Question 19

What reagent(s)would accomplish the following transformation?

A) Pyridinium chlorochromate
B) LiAlD₄ then H₃O⁺
C) H₂CrO₄
D) Potassium dichromate
E) H₂SO₄

Question 20

Which of the following reagents would accomplish the reaction shown?

A) H₂SO₄,H₂O
B) H₂CrO₄
C) O₂ (slow)
D) HO^-,H₂O
E) None of the above.

Question 21

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

A) NaH
B) LiAlD₄
C) NaBH₄
D) H₃O⁺
E) All of the above.

Question 22

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

A)

B)

C)

D)

E)

Question 23

For this series of alcohols,which one will have an equilibria that lies the furthest to the right in a basic solution?

A) CH₃OH
B) FCH₂OH
C) ClCH₂OH
D) BrCH₂OH
E) All equilibria will be the same.

Question 24

What is the product of the following reaction?

A)

B)

C)

D)

E) All of the above are the end products of this reaction.

Question 25

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)

B)

C)

D)

E)

Question 26

Which of these reactions will give the product shown?

A)

B)

C)

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

Question 27

Ingestion of which of the following toxic alcohols can cause blindness?

A) CH₃OH
B) CH₃CH₂OH
C) (CH₃)₂CHOH
D) C₆H₅OH
E) HOCH₂CH₂OH

Question 28

What would be the expected product for the following reaction?

A)

B)

C)

D) CH₃CH₂CD₂CH₃
E)

Question 29

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

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

Question 30

Predict the major product of the following reaction:

A)

B)

C)

D)

E) No reaction occurs.

Question 31

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

A)

B)

C)

D)

E)

Question 32

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

A)

B)

C)

D) All of the above.
E) Two of the above.

Question 33

For the transformations below,what is the structure of the starting material?

A)

B)

C)

D)

E)

Question 34

What is the major product of the following reaction?

A)

B)

C)

D)

E)

Question 35

What is the product of the following reaction?

A)

B)

C)

D)

E)

Question 36

Identify the reagent that you would use to go from PGE₁ to PGE_{1 $\alpha$} ?

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

Question 37

Which of these reagents will best accomplish the transformation below?

A) NaOH,H₂O
B)

C)

D)

E) None of the above.

Question 38

What is the product of the following reaction?

A)

B)

C)

D)

E) None of the above.

Question 39

Rank the following organic compounds in order of increasing acidity.

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