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

Question 1

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

Answer 1

Question 2

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

Answer 2

(E)-2-ethyl-but-2-en-1-ol

Question 3

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

Answer 3

Question 4

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

Question 5

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 6

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 7

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 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 _____.

Question 9

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 10

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

Question 11

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

Refer to instructions.
a)The weakest acid in the table is _____.
b)Which of the acids in the table has the weakest conjugate base?

Question 12

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

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

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 15

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

Question 16

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

Question 17

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 18

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 19

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

Question 20

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

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

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. _____

A)CrO₃, H₂SO₄, H₂O
B)1. NaBH₄, ethanol
2. H₃O⁺
C)1. LiAl₄, ether
2. H₃O⁺
D)periodinane

Question 23

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

Question 24

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

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

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. _____

A)CrO₃, H₂SO₄, H₂O
B)1. NaBH₄, ethanol
2. H₃O⁺
C)1. LiAl₄, ether
2. H₃O⁺
D)periodinane

Question 28

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: ______

A)CrO₃, H₂SO₄, H₂O
B)1. NaBH₄, ethanol
2. H₃O⁺
C)1. LiAl₄, ether
2. H₃O⁺
D)periodinane

Question 29

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 30

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 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

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

Question 33

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

Question 34

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 35

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 36

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