Organic Chemistry 8th Edition By L. G. Wade – Test Bank

Chapter 11 Reactions of Alcohols

1) Classify the reaction below as an oxidation, a reduction, or neither.

(CH3)2CHCH2OH → (CH3)2CHCHO
A) oxidation
B) reduction
C) neither
Answer: A
Diff: 1
Section: 11.1

2) Classify the reaction below as an oxidation, a reduction, or neither.

PhCO2H → PhCH2OH
A) oxidation
B) reduction
C) neither
Answer: B
Diff: 1
Section: 11.1

3) Classify the reaction below as an oxidation, a reduction, or neither.

cis-pent-2-ene → pentane
A) oxidation
B) reduction
C) neither
Answer: B
Diff: 1
Section: 11.1

4) Which of the following reagents is not typically viewed as an oxidizing agent?
A) Cl2
B) KMnO4
C) O2
D) KCl
E) H2O2
Answer: D
Diff: 2
Section: 11.1

5) Which of the following compounds has carbon in the highest oxidation state?
A) CO2
B) CH3C(O)CH3
C) CH3CH2OH
D) CH3C(OCH2CH3)3
Answer: A
Diff: 2
Section: 11.1

6) Circle all carbon centers that are at the same oxidation state as a carboxylic acid.

Answer:

Diff: 2
Section: 11.1

7) In the chromic acid oxidation of alcohols, the chromium is:
A) oxidized from Cr+3 to Cr+6.
B) reduced from Cr+6 to Cr+3.
C) oxidized from Cr+6 to Cr+3.
D) reduced from Cr+3 to Cr+6.
E) none of the above
Answer: B
Diff: 1
Section: 11.2

8) What series of synthetic steps could be used to carry out the transformation shown below?

Answer:
1. BH3
2. H2O2, -OH
3. PCC
Diff: 1
Section: 11.2

9) Which of the following alcohols will give a positive chromic acid test?
A) tert-butanol
B) cyclohexanol
C) pentan-3-ol
D) both A and B
E) both B and C
Answer: E
Diff: 2
Section: 11.2

10) Which of the following reagents is the best choice for oxidizing a primary alcohol to an aldehyde?
A) H2CrO4
B) pyridinium chlorochromate
C) Na2Cr2O7, H2SO4
D) KMnO4
E) LiAlH4
Answer: B
Diff: 2
Section: 11.2

11) Which alcohol reacts most rapidly with the Lucas reagent?
A) benzyl alcohol
B) methanol
C) 2-propanol
D) isobutanol
Answer: A
Diff: 2
Section: 11.2