Deck 13: Alcohols, Phenols, and Thiols; Ethers and Sulfides

Question 1

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

Answer 1

2° alcohol

Question 2

Provide correct IUPAC names for each of the structures below.
Name:

Answer 2

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

Question 3

To answer the following question(s), consider the reaction below.
Refer to instructions. Provide the IUPAC name for the product alcohol.

Answer 3

trans-2-methylcyclohexanol

Question 4

To answer the following question(s), consider the reaction below.
Refer to instructions. Provide the complete IUPAC name for the starting material in this reaction and classify the alcohol as primary, secondary, or tertiary.

Question 5

Draw structures corresponding to each of the following IUPAC names.
Draw:
3-methylbut-2-en-1-ol

Question 6

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 S_N1 process
C) an E2 process
D) an S_N2 process

Question 7

Consider the Grignard reaction below to answer the following question(s).
Predict the product of the following reaction.

Question 8

Provide correct IUPAC names for each of the structures below.
Name:

Question 9

Draw structures corresponding to each of the following IUPAC names.
Draw:
allyl benzyl ether

Question 10

Consider the Grignard reaction below to answer the following question(s).
Refer to instructions. The nucleophile in this reaction is indicated by letter _____.

A)A
B)B
C)C

Question 11

To answer the following question(s), consider the reaction below.
Refer to instructions. The conversion of an alcohol into an alkyl chloride by reaction with SOCl₂ is an example of:

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

Question 12

Consider the Grignard reaction below to answer the following question(s).
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

Question 13

Draw structures corresponding to each of the following IUPAC names.
Draw:
2, 4, 6-trinitrophenol

Question 14

Draw structures corresponding to each of the following IUPAC names.
Draw:
3-methylbutane-1-thiol

Question 15

Draw structures corresponding to each of the following IUPAC names.
Draw:
2-phenylpropan-2-ol

Question 16

To answer the following question(s), consider the reaction below.
Refer to instructions. On the templates provided below, draw both conformations of the alcohol product. Circle the least stable conformation.

Question 17

Consider the Grignard reaction below to answer the following question(s).
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.

Question 18

Which of the following would not react with either Na₂Cr₂O₇ or pyridinium chlorochromate? A B C D ​

A) only A
B) only C
C) only B and D
D) A, B, C, and D

Question 19

Consider the Grignard reaction below to answer the following question(s).
Refer to instructions. The electrophile in this reaction is indicated by letter _____.

A)A
B)B
C)C

Question 20

Draw structures corresponding to each of the following IUPAC names.
Draw:
cyclopropyl ethyl sulfide

Question 21

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

Question 22

What is the IUPAC name of the following compound?

A) cis-4-methylcyclohexanol
B) trans-4-methylcyclohexanol
C) cis-4-hydroxy-1-methylcyclohexane
D) trans-4-hydroxy-1-methylcyclohexane

Question 23

Which of the following is probably the least useful in IR characterization of a compound?

A) phenol: 3500 cm−¹
B) alcohol: 3500 cm−¹
C) phenol: 1500−1600 cm−¹
D) ether: 1050−1150 cm−¹
E) all of these are about equally useful

Question 24

Which of the following ethers cannot be prepared by a Williamson ether synthesis?

A) tert-butyl phenyl ether
B) isopropyl methyl ether
C) anisole
D) tert-butyl methyl ether

Question 25

Predict the product of the following reaction.

Question 26

Predict the product in each step of the following reaction.

Question 27

What is the best choice of reagent to achieve the following transformation?

A) CrO₃, H₃O⁺, acetone
B) pyridium chlorochromate, CH₂Cl₂
C) SOCl₂, pyridine
D) NaBH₄, H₃O⁺
E) LiAlH₄, H₃O⁺

Question 28

What is the IUPAC name of the following compound?

A) ethyl isopropyl thiol
B) 2-methylsulfanylpropane
C) ethyl isopropyl disulfide
D) ethyl isopropyl sulfide

Question 29

Addition of chlorotrimethylsilane to an alcohol

A) results in an S_N1 reaction.
B) requires acidic reaction conditions.
C) is sterically hindered by the three methyl groups.
D) results in the formation of an ether.
E) produces a more reactive species.

Question 30

Which of the following are ethers? A B C D ​

A) only A and B
B) only A and D
C) only A, B, and C
D) all of these are ethers

Question 31

Identify the m/z peak for the alpha cleavage and the peak for the dehydration of the following alcohol.

Question 32

The following IR spectrum would most likely be associated with

A) phenol
B) aromatic alcohol
C) aliphatic alcohol
D) ether
E) cannot determine from the isolated spectrum

Question 33

What is the major organic product obtained from the following reaction?

A)

B)

C)

D)

Question 34

Predict the major products of the following by drawing the structures of A and B.

Question 35

Which of the following is not a property of a protecting group?

A) change the reactivity of a functional group
B) inert to reaction conditions
C) becomes a permanent part of the product
D) alters the mechanism of the desired reaction
E) all of these are properties of a protecting group

Question 36

How would you synthesize the following class of quinones (ubiquinones) from the corresponding hydroquinones?

Question 37

Answer the following questions.
a)Identify the peak for the carbon indicted by the arrow on the ¹³C NMR spectra.
b)What type of signal would be expected in the 1H NMR spectrum for the hydrogen atom indicated with the arrow?
a. singlet
b. triplet
c. quintet
d. sextet
e. quartet of triplets (eight peaks)

Question 38

What is the best way to make the following ether by a Williamson ether synthesis?