Organic Chemistry with Biological Applications 3rd Edition by John E. McMurry – Test Bank

Organic Chemistry with Biological Applications 3rd Edition by John E. McMurry – Test Bank

Chapter 13

Instructions: Draw structures corresponding to each of the following IUPAC names.

1. Draw:

3-methylbut-2-en-1-ol
ANSWER:
POINTS: 1

2. Draw:

2-phenylpropan-2-ol
ANSWER:
POINTS: 1

3. Draw:

2, 4, 6-trinitrophenol
ANSWER:
POINTS: 1

Instructions: Refer to the data below to answer the following question(s).

pKas of Some Phenols Y pKa
−H 9.89
m-NO2 8.28
p-NO2 7.17
m-OCH3 9.65
p-OCH3 10.21

4. Refer to instructions.

a) The weakest acid in the table is _____.

b) Which of the acids in the table has the weakest conjugate base?
ANSWER: a) p-methoxyphenol

b) p-nitrophenol

POINTS: 1

5. Refer to instructions. Arrange the following in order of increasing acidity:

p-hydroxyphenol p-methylphenol p-fluorophenol
ANSWER: p-methylphenol < p-hydroxyphenol < p-fluorophenol
POINTS: 1

Instructions: To answer the following question(s), consider the reaction below.

6. Refer to instructions. The alcohol product is classified as a:
a. 1° alcohol
b. 2° alcohol
c. 3° alcohol
d. 4° alcohol
ANSWER: b
POINTS: 1

7. Refer to instructions. On the templates provided below, draw both conformations of the alcohol product. Circle the least stable conformation.

ANSWER:
POINTS: 1

8. Refer to instructions. Provide the IUPAC name for the product alcohol.
ANSWER: trans-2-methylcyclohexanol
POINTS: 1

Instructions: To answer the following question(s), consider the reaction below.

9. Refer to instructions. Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary, secondary, or tertiary.
ANSWER: (R)-heptan-2-ol, secondary
POINTS: 1