Deck 10: Reactions of Alcohols, Ethers,epoxides, Amines, and Sulfur-Containing Compounds

Question 1

Which of the following statements is not true?

A) Primary, secondary, and tertiary alcohols all undergo nucleophilic substitution with HI, HBr, and HCl.
B) Carbocation stability: 1° > 2° > 3°
C) Tertiary alcohols undergo S_N1 reactions with hydrogen halides.
D) Primary alcohols undergo S_N2 reactions with hydrogen halides.
E) An alcohol has a strongly basic leaving group that cannot be displaced by a nucleophile.

Answer 1

Carbocation stability: 1° > 2° > 3°

Question 2

Which alkene is the major product of this dehydration?

A)
B)
C)
D)
E)

Answer 2

Question 3

Using reagents such as SOCl₂ or PBr₃, alcohols are converted into alkyl halides. This approach ____________.

A) inverts the configuration if the OH group is bonded to an asymmetric center
B) converts the OH group into a better leaving group
C) works well for 1° and 2° alcohols
D) creates a leaving group that is a weaker base than the halide ion
E) does all of the above

Answer 3

does all of the above

Question 4

In the reaction of the following alcohol, what type of reaction is involved in the transformation?

A) S_N1
B) S_N2
C) E1
D) E2
E) an anti-Zaitzev elimination

Question 5

Which set of reaction conditions will produce the indicated product?

A) 1. TsCl/pyridine 2. NaCN
B) PBr₃/pyridine 2. NaCN
C) SOCl₂/pyridine 2. NaCN
D) PCl₃/pyridine 2. NaCN
E) B, C, and D will all work.

Question 6

Which of the following reagents can be used to prepare an aldehyde from a 1° alcohol?

A) 1. DMSO/oxalyl chloride (COCl)₂ 2. (Et)₃N
B) Na₂Cr₂O₇/H₂SO₄/H₂O
C) PCC/pyridine/CH₂Cl₂
D) NaOCl/acetic acid
E) A, C, and D

Question 7

Which alcohol will not undergo a chromic acid oxidation?

A)
B)
C)
D)
E)

Question 8

What is the major product of this reaction?

A)
B)
C)
D)
E) A and B

Question 9

What is the major product of the following reaction?

A)
B)
C)
D)
E)

Question 10

SAM is a very good methylating agent in biological systems because the transferred methyl group
____________.

A) was attached to a large molecule
B) was attached to a water-soluble molecule
C) occurred in a polar protic solvent
D) was attached to a sulfonium ion
E) None of the above are true.