Fundamentals of Organic Chemistry 7th Edition Mcmurry Test Bank

Fundamentals of Organic Chemistry 7th
Edition McMurry Test Bank

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Chapter 8 - Alcohols, Phenols, Ethers, and Their Sulfur
Analogs
Student: ___________________________________________________________________________
1. Instructions: Draw structures corresponding to each of the following IUPAC names.
Draw:
3-methylbut-2-en-1-ol
Draw:
2-phenylpropan-2-ol
Draw:
2, 4, 6-trinitrophenol
4. 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
Refer to instructions.
a) The weakest acid in the table is _____.
b) Which of the acids in the table has the weakest conjugate base?
5. Instructions: To answer the following question(s), consider the reaction below.
Refer to instructions. The alcohol product is classified as a:

A. 1 alcohol
B. 2 alcohol
C. 3 alcohol
D. 4 alcohol
Refer to instructions. On the templates provided below, draw both conformations of the alcohol product. Circle
the least stable conformation.
Refer to instructions. Provide the IUPAC name for the product alcohol.
8. Instructions: Consider the Grignard reaction below to answer the following question(s).
Refer to instructions. The electrophile in this reaction is indicated by letter _____.

Refer to instructions. The nucleophile in this reaction is indicated by letter _____.
Refer to instructions. If a secondary alcohol were desired as a product of the reaction, B should be replaced
with
A. an ester
B. an aldehyde
C. formaldehyde (methanal)
D. a primary alcohol
11. A useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl
compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each
alcohol below. List all possibilities.
Draw:
3-methylbutane-1-thiol
Draw:
cyclopropyl ethyl sulfide

Draw:
Dicyclohexyl sulfide
15. Instructions: Provide correct IUPAC names for each of the structures below.
Name:
Name:
Name:
18. Instructions: Consider the reaction below to answer the following question.
Refer to instructions. Mechanistically, the Williamson ether synthesis outlined above is:
A. an E1 process
B. an SN1 process
C. an E2 process
D. an SN2 process
Refer to instructions. On the structures provided below draw arrows showing the mechanism of step two of
this reaction.
20. Which of the following would not react with either Na2Cr2O7 or periodinane?
1 2 3 4
A. only 1
B. only 3
C. only 2 and 4
D. 1, 2, 3 and 4
21. Answer the following questions.
a) Which of the following would

produce an aldehyde when reacted
with periodinane?
1 2 3
a. only 1
b. only 3
c. only 1 and 3
d. only 2 and 3
b) If CrO3 were used in place of

periodinane, how would the product
of the reaction differ?
a. a ketone would be produced
b. a carboxylic acid would be
produced.
c. a mixture of aldehyde and ketone
would be produced
d. the reaction product would be the
same in both cases
22. What is the IUPAC name of the following compound?
A. cyclohexen-3-ol
B. cyclohexen-2-ol
C. cyclohex-1-en-3-ol
D. cyclohex-2-en-1-ol
A. cis-4-methylcyclohexanol
B. trans-4-methylcyclohexanol
C. cis-4-hydroxy-1-methylcyclohexane
D. trans-4-hydroxy-1-methylcyclohexane
24. Which of the following are ethers?
1 2 3 4
A. only 1 and 2
B. only 1 and 4
C. only 1, 2 and 3
D. all of these are ethers
A. ethyl isopropyl thiol

B. 2-methylsulfanylpropane
C. ethyl isopropyl disulfide
D. ethyl isopropyl sulfide
26. What is the best way to make the following ether by a Williamson ether synthesis?
27. Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant
stereochemistry.
Write the product(s):

28. Instructions:
stereochemistry.
29. Instructions:
stereochemistry.

30. Instructions:
stereochemistry.
31. Instructions:
stereochemistry.

32. Instructions:
stereochemistry.
33. Instructions:
stereochemistry.

34. Instructions:
stereochemistry.
35. Instructions:
Choose the best reagent(s) for carrying out the following conversions from the list provided below. Place the
letter of the best choice in the blank. Reagents may be used more than once.
a. CrO3, H2SO4, H2O

b. 1. NaBH4, ethanol
2. H3O+
c. 1. LiAl4, ether
2. H3O+
d. periodinane
Refer to instructions: ______

36. Instructions:
a. CrO3, H2SO4, H2O

2. H3O+
c. 1. LiAl4, ether
2. H3O+
d. periodinane
Refer to instructions. _____
37. Instructions:
a. CrO3, H2SO4, H2O

2. H3O+
c. 1. LiAl4, ether
2. H3O+
d. periodinane
38. Choose the best reagent for carrying out the following reactions from the list below. Place the letter of the
reagent(s) in the box over the reaction arrow. Only one letter per box.
A. m-ClC6H4CO3H B. H2/Pd
C. warm H2SO4/H2O D. PCC, CH2Cl2
E. LiAlH4 in ether, then H3O+ F. NaOH, heat

Chapter 8 - Alcohols, Phenols, Ethers, and Their Sulfur Analogs
Key
Draw:
3-methylbut-2-en-1-ol
Draw:
2-phenylpropan-2-ol
Draw:
2, 4, 6-trinitrophenol
4. 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
Refer to instructions.
a) The weakest acid in the table is _____.
b) Which of the acids in the table has the weakest conjugate base?
a) p-methoxyphenol
b) p-nitrophenol
Refer to instructions. The alcohol product is classified as a:

A. 1 alcohol
B. 2 alcohol
C. 3 alcohol
D. 4 alcohol
Refer to instructions. On the templates provided below, draw both conformations of the alcohol product. Circle
the least stable conformation.
Refer to instructions. Provide the IUPAC name for the product alcohol.
trans-2-methylcyclohexanol
Refer to instructions. The electrophile in this reaction is indicated by letter _____.
Refer to instructions. The nucleophile in this reaction is indicated by letter _____.
Refer to instructions. If a secondary alcohol were desired as a product of the reaction, B should be replaced
with
A. an ester
B. an aldehyde
C. formaldehyde (methanal)
D. a primary alcohol
11. A useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl
compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare each
alcohol below. List all possibilities.
Draw:
3-methylbutane-1-thiol
Draw:
cyclopropyl ethyl sulfide

Draw:
Dicyclohexyl sulfide
Name:
1-ethoxy-2,2-dimethylpropane or ethyl 2,2-dimethylpropyl ether
Name:
(E)-2-ethyl-but-2-en-1-ol
Name:
trans-cycloheptane-1,3-diol
Refer to instructions. Mechanistically, the Williamson ether synthesis outlined above is:
A. an E1 process
B. an SN1 process
C. an E2 process
D. an SN2 process
Refer to instructions. On the structures provided below draw arrows showing the mechanism of step two of
this reaction.
20. Which of the following would not react with either Na2Cr2O7 or periodinane?
1 2 3 4
A. only 1
B. only 3
C. only 2 and 4
D. 1, 2, 3 and 4
21. Answer the following questions.
a) Which of the following would

produce an aldehyde when reacted
with periodinane?
1 2 3
a. only 1
b. only 3
c. only 1 and 3
d. only 2 and 3
b) If CrO3 were used in place of

periodinane, how would the product
of the reaction differ?
a. a ketone would be produced
b. a carboxylic acid would be
produced.
c. a mixture of aldehyde and ketone
would be produced
d. the reaction product would be the
same in both cases
a) a
b) b
A. cyclohexen-3-ol
B. cyclohexen-2-ol
C. cyclohex-1-en-3-ol
D. cyclohex-2-en-1-ol
A. cis-4-methylcyclohexanol
B. trans-4-methylcyclohexanol
C. cis-4-hydroxy-1-methylcyclohexane
D. trans-4-hydroxy-1-methylcyclohexane
24. Which of the following are ethers?
1 2 3 4
A. only 1 and 2
B. only 1 and 4
C. only 1, 2 and 3
D. all of these are ethers
A. ethyl isopropyl thiol

B. 2-methylsulfanylpropane
C. ethyl isopropyl disulfide
D. ethyl isopropyl sulfide
26. What is the best way to make the following ether by a Williamson ether synthesis?
27. Instructions:
stereochemistry.
28. Instructions:
stereochemistry.

29. Instructions:
stereochemistry.
30. Instructions:
stereochemistry.

31. Instructions:
stereochemistry.
32. Instructions:
stereochemistry.

33. Instructions:
stereochemistry.
34. Instructions:
stereochemistry.

35. Instructions:
a. CrO3, H2SO4, H2O

2. H3O+
c. 1. LiAl4, ether
2. H3O+
d. periodinane
Refer to instructions: ______
36. Instructions:
a. CrO3, H2SO4, H2O

2. H3O+
c. 1. LiAl4, ether
2. H3O+
d. periodinane
b
37. Instructions:
a. CrO3, H2SO4, H2O

2. H3O+
c. 1. LiAl4, ether
2. H3O+
d. periodinane
38. Choose the best reagent for carrying out the following reactions from the list below. Place the letter of the
reagent(s) in the box over the reaction arrow. Only one letter per box.
A. m-ClC6H4CO3H B. H2/Pd
C. warm H2SO4/H2O D. PCC, CH2Cl2
E. LiAlH4 in ether, then H3O+ F. NaOH, heat

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Fundamentals of Organic Chemistry 7th

Edition McMurry Test Bank

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

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

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

pKas of Some Phenols Y pKa

a) The weakest acid in the table is _____.

Refer to instructions. The alcohol product is classified as a:

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

Refer to instructions. The electrophile in this reaction is indicated by letter _____.

Refer to instructions. The nucleophile in this reaction is indicated by letter _____.

cyclopropyl ethyl sulfide

a) Which of the following would

b) If CrO3 were used in place of

22. What is the IUPAC name of the following compound?

24. Which of the following are ethers?

25. What is the IUPAC name of the following compound?

A. ethyl isopropyl thiol

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

a. CrO3, H2SO4, H2O

Refer to instructions: ______

a. CrO3, H2SO4, H2O

Refer to instructions. _____

a. CrO3, H2SO4, H2O

C. warm H2SO4/H2O D. PCC, CH2Cl2

E. LiAlH4 in ether, then H3O+ F. NaOH, heat

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

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

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

pKas of Some Phenols Y pKa

a) The weakest acid in the table is _____.

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

Refer to instructions. The alcohol product is classified as a:

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

Refer to instructions. The electrophile in this reaction is indicated by letter _____.

Refer to instructions. The nucleophile in this reaction is indicated by letter _____.

cyclopropyl ethyl sulfide

1-ethoxy-2,2-dimethylpropane or ethyl 2,2-dimethylpropyl ether

21. Answer the following questions.

a) Which of the following would

b) If CrO3 were used in place of

23. What is the IUPAC name of the following compound?

24. Which of the following are ethers?

25. What is the IUPAC name of the following compound?

A. ethyl isopropyl thiol

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

Write the product(s):

a. CrO3, H2SO4, H2O

Refer to instructions: ______

a. CrO3, H2SO4, H2O

Refer to instructions. _____