Deck 17: Alcohols and Phenols

Question 1

Draw: 2-phenyl-2-propanol

Answer 1

Question 2

Exhibit 17-2
Refer to the data below to answer the following question(s).
pK_as of Some Phenols Y
pK_a
−H
9.89
m-NO₂
8.28
p-NO₂
7.17
m-OCH₃
9.65
p-OCH₃
10.21
Refer to Exhibit 17-2.The weakest acid in the table is:

Answer 2

p-methoxyphenol

Question 3

Refer to Exhibit 17-3.On the templates provided below,draw both conformations of the alcohol product.Circle the least stable conformation.

Answer 3

Question 4

Exhibit 17-4
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-4.On the structures provided below,draw arrows which account for the complete stepwise mechanism for this reaction.

Question 5

Explain why nonafluoro-2-methyl-2-propoxide is a much weaker base than tert-butoxide.

Question 6

Refer to Exhibit 17-3.Provide the IUPAC name for the product alcohol.

Question 7

H₂O₂,−OH

Question 8

Exhibit 17-4
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-4.The dehydration of secondary and tertiary alcohols by reaction with POCl₃ in pyridine is an example of:

A)an E1 process
B)an S_N1 process
C)an E2 process
D)an S_N2 process

Question 9

Refer to Exhibit 17-3.The alcohol product is classified as a:

A)1° alcohol
B)2° alcohol
C)3° alcohol
D)4° alcohol

Question 10

Draw: cis-4-tert-butylcyclohexanol

Question 11

Name:
HOCH₂CH₂OH

Question 12

Draw: glycerol

Question 13

Name:

Question 14

Exhibit 17-2
Refer to the data below to answer the following question(s).
pK_as of Some Phenols Y
pK_a
−H
9.89
m-NO₂
8.28
p-NO₂
7.17
m-OCH₃
9.65
p-OCH₃
10.21
Refer to Exhibit 17-2.How do you account for the difference in acidity between meta and para-nitrophenol?

Question 15

Draw: 3-methyl-2-buten-1-ol

Question 16

Draw: 2,4,6-trinitrophenol

Question 17

Name:

Question 18

Name:

Question 19

Exhibit 17-4
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-4.Why is 3-methylcyclohexene the major product of this reaction instead of 1-methycyclohexene?

Question 20

Exhibit 17-2
Refer to the data below to answer the following question(s).
pK_as of Some Phenols Y
pK_a
−H
9.89
m-NO₂
8.28
p-NO₂
7.17
m-OCH₃
9.65
p-OCH₃
10.21
Refer to Exhibit 17-2.Which of the acids in the Table has the weakest conjugate base?

Question 21

Exhibit 17-5
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-5.Write the complete stepwise mechanism for the reaction.Show all intermediates and all electron flow with arrows.

Question 22

Outline the synthetic steps necessary to carry out the conversion below.You may use any organic or inorganic reagents you need.Show the structures of all intermediate compounds that would probably be isolated during the course of your synthesis,and show all necessary reagents.

Question 23

Synthesize the following alcohol starting with cyclohexene and bromocylopentane as the only organic starting materials.Show all reagents and all intermediates in your synthesis.
​

Question 24

What product is formed when the following substance is treated with CrO₃ under appropriate conditions?

A)
B)
C)
D)
E)No reaction occurs under these conditions.

Question 25

Which signal in the following proton NMR is due to an alcohol proton?

A)1
B)2
C)3
D)4
E)This cannot be determined from the data presented in the spectrum.

Question 26

Exhibit 17-6
Consider the Grignard reaction below to answer the following question(s).
Refer to Exhibit 17-6.The nucleophile in this reaction is:

Question 27

Exhibit 17-5
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-5.The starting material can be classified as a:

A)1° alcohol
B)2° alcohol
C)3° alcohol
D)4° alcohol

Question 28

Exhibit 17-5
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-5.Provide the complete IUPAC name for the starting material in this reaction.

Question 29

Give the IUPAC name for the following compound.

Question 30

In a proton NMR,the signal for the -OH proton

A)will generally be upfield from the corresponding alkyl signal.
B)is generally unsplit by adjacent protons.
C)is lost due to exchange with acidic impurities.
D)covers a broader chemical shift range than a phenol -OH.

Question 31

Exhibit 17-6
Consider the Grignard reaction below to answer the following question(s).
Refer to Exhibit 17-6.The alcohol product can be classified as a:

A)1° alcohol
B)2° alcohol
C)3° alcohol
D)4° alcohol

Question 32

2,4,6-trinitrophenol is a stronger acid than phosphoric acid.Another name for this compound is picric acid.Explain the acidity of picric acid.

Question 33

Classify the following alcohol.Atoms other than carbon and hydrogen are labeled.

A)primary
B)secondary
C)tertiary

Question 34

Which of the peak in the IR spectrum shown is due to the C-O stretch in an alcohol?

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

Question 35

Exhibit 17-6
Consider the Grignard reaction below to answer the following question(s).
Refer to Exhibit 17-6.The electrophile in this reaction is:

Question 36

Exhibit 17-5
To answer the following question(s),consider the reaction below:
Refer to Exhibit 17-5.The conversion of an alcohol into an alkyl chloride by reaction with SOC1₂ is an example of:

A)an E1 process
B)an S_N1 process
C)an E2 process
D)an S_N2 process

Question 37

Which of the following would have the highest boiling point?

A)butane
B)1- butanol
C)chloropropane
D)pentane

Question 38

Which of the following would be the most acidic?

A)p-nitrophenol
B)phenol
C)p-chlorophenol
D)p-methylphenol

Question 39

Propose a synthesis of Dimestrol starting from p-methoxypropiophenone as the only source of carbon.

Question 40

Acid-catalyzed dehydration of 2,2-dimethylcyclohexanol yields 1,2-dimethylcyclohexene as one of the major products.Write the complete stepwise mechanism for this reaction.Show all electron flow with arrows and show all intermediate structures.

Question 41

​Draw the resonance forms of 4-nitro-m-cresol.

Question 42

​Draw the mechanism for the acid-catalyzed dehydration of 2-methyl-2-pentanol to yield 2-methyl-1-butene.

Question 43

​Draw the mechanism of the E2 reaction involving the dehydration of 3-methyl-1-cyclohexanol,when reacting with POCl₃ in pyridine.

Question 44

The mass spectrum for the following compound would have a peak at which m/z ratio due to dehydration? Atoms other than carbon and hydrogen are labeled.

A)116
B)98
C)87
D)59