Deck 8: Alcohols, Phenols, Ethers, and Their Sulfur Analogs

Question 1

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

Answer 1

trans-2-methylcyclohexanol

Question 2

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

Answer 2

Question 3

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

Answer 3

Question 4

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

Question 5

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 6

Instructions: Consider the reaction below to answer the following question. Refer to instructions. On the structures provided below draw arrows showing the mechanism of step two of this reaction.

Question 7

Instructions: To answer the following question(s), consider the reaction below. Refer to instructions. The alcohol product is classified as a:

A) 1 $\degree$ alcohol
B) 2 $\degree$ alcohol
C) 3 $\degree$ alcohol
D) 4 $\degree$ alcohol

Question 8

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

Question 9

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

Question 10

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

Question 11

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

Question 12

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

Question 13

Instructions: 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 14

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

Question 15

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

Question 16

Which of the following would not react with either Na₂Cr₂O₇ or periodinane?

A) only 1
B) only 3
C) only 2 and 4
D) 1, 2, 3 and 4

Question 17

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

Question 18

Instructions: 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 19

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

Question 20

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

Question 21

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 22

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 23

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.
Refer to instructions: ______

Question 24

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 25

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 26

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 27

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 28

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 29

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 30

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

Question 31

Instructions:
Give the major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry.
Write the product(s):

Question 32

Which of the following are ethers?

A) only 1 and 2
B) only 1 and 4
C) only 1, 2 and 3
D) all of these are ethers

Question 33

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.
Refer to instructions. _____

Question 34

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 35

Answer the following questions.

Question 36

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.
Refer to instructions. _____

Question 37

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