Name: __________________________ Date: _____________

Practice Test - Alcohols, Phenols, Thiols, and Ethers

1.
Compound I is a(n) _____ and compound II is a(n) _____.
I.
II.
 
A.
alcohol; phenol
B.
ether; alcohol
C.
phenol; ether
D.
alcohol; ether


2.
What is true about theses structures?
A.
All three structures represent constitutional isomers.
B.
Structures II and III are the same compound.
C.
Structures II and III represent constitutional isomers of an alcohol.
D.
Structures I and III are the same compound.


3.
Which compounds are capable of hydrogen bonding with themselves?
A.
I and II only
B.
II and III only
C.
I and III only
D.
I, II, and III


4.
Which compounds are capable of hydrogen bonding to water?
 
I.
1-hexanol
II.
1,4-pentanediol
III.
octane
IV. isopropylmethyl ether
 
A.
I, II, III, and IV
B.
III only
C.
I, II and IV only
D.
I , II, and III only


5.
Which alcohols will undergo dehydration?
    I.     1-pentanol     II.     2-methyl-2-butanol     III.     t-butyl alcohol
A.
I and II only
B.
II and III only
C.
I and III only
D.
I, II, and III


6.
Which alcohols will undergo dehydration and form only one product?
    I.     1-pentanol     II.     3-methyl-2-butanol     III.     t-butyl alcohol
A.
I and II only
B.
II and III only
C.
I and III only
D.
I, II, and III


7.
Which alcohols undergo dehydration and produce two different products?
 
I.
1-pentanol
II.
2-methyl-2-pentanol
III.
s-butyl alcohol
 
A.
I and II only
B.
II and III only
C.
I and III only
D.
I, II, and III


8.
What is the major product of dehydration of 2-methyl-2-butanol?
A.
2-methyl-1-butene
B.
2-methyl-2-butene
C.
The reaction will produce equal amounts of 2-methyl-1-butene and 2-methyl-2-butene
D.
2-methyl-3-butene.


9.
Choose the correct set of answers for the oxidation of these compounds.
 
I.
1-pentanol
II.
2-methyl-2-pentanol
III.
isobutyl alcohol
 
A.
I and II only will produce a aldehydes under the proper conditions.
B.
I and III only will produce a aldehydes under the proper conditions.
C.
II and III only will produce a aldehydes under the proper conditions.
D.
I only will produce an aldehyde under the proper conditions.


10.
Upon oxidation, which of these compounds will produce a ketone?
 
I.
2-pentanol
II.
2-methyl-2-butanol
III.
t-butyl alcohol
 
A.
I only
B.
II only
C.
III only
D.
II and III only


11.
Which compound will oxidize to produce a carboxylic acid under the proper conditions?
A.
B.
CH3CH2CH2CH2OH
C.
CH3CH2CH2-O-CH3
D.
(CH3)3COH


12.
When purple potassium permanganate is added to an unknown solution, the purple color disappears. Which compound(s) decolorize potassium permanganate?
 
I.
1-pentanol
II.
2-pentanol
III.
2-pentene
 
A.
I only
B.
II only
C.
III only
D.
I, II, and III all decolorize potassium permanganate


13.
When orange potassium dichromate is added to an unknown solution, the orange color changes to green. Which compound(s) could cause this color change?
A.
I only
B.
II only
C.
III only
D.
I and II only


14.
What is the correct name of this compound?
A.
2-ethyl-3,4-dimethyl-2-pentanol
B.
4-ethyl-2,3-dimethyl-4-pentanol
C.
2-ethyl-2-hydroxy-3,4-dimethylhexane
D.
3,4,5-trimethyl-3-hexanol


15.
What is the correct name of this compound?
 
(CH3)2CH-O-C(CH3)3
 
A.
butyl propyl ether
B.
isopropyl t-butyl ether
C.
s-propyl t-butyl ether
D.
isobutyl isopropyl ether


16.
Which is the correct structure for 4-ethoxyphenol?
A.
B.
C.
D.


17.
What is the correct IUPAC name for this compound?
A.
1-hydroxy-3-methyl-6-isopropylbenzene
B.
5-methyl-2-t-butylphenol
C.
2-t-butyl-5-methylphenol
D.
3-hydroxy-4-t-butyl-1-methylbenzene


18.
The correct name for this compound is:
 
C6H5-CH2CH2-OH
 
A.
2-benzyl-2-ethanol
B.
2-benzyl-1-ethanol
C.
2-phenyl-2-ethanol
D.
2-phenyl-1-ethanol


19.
Which is(are) the product(s) of the reaction of ethanol with sulfuric acid at 180ºC?
A.
ethene + water
B.
diethyl ether + water
C.
a mixture of equal amounts of ethane + diethyl ether + water
D.
a carboxylic acid


20.
How many different functional types of groups are present in this compound?
A.
1
B.
2
C.
3
D.
4


21.
What functional groups are present in this structure?
A.
two alcohols and one ether
B.
one alcohol and two ethers
C.
one alcohol, one ether, and one phenol
D.
one phenol and one diol


22.
Which compounds can hydrogen bond with themselves?
 
I.
ethanol
II.
diethyl ether
III.
bromophenol
 
A.
I and II only
B.
II and III only
C.
I and III only
D.
I, II and III


23.
Which reagent, when added to 1-pentanol, produces an aldehyde under the correct conditions?
A.
H2SO4
B.
K2Cr2O7
C.
Na
D.
NaOH


24.
Which reagent, when added to 1-pentanol, produces a ketone?
A.
H2SO4
B.
NaOH
C.
KMnO4
D.
1-pentanol does not react to produce a ketone.


25.
The product of this reaction is:
A.
an aldehyde, depending on the conditions
B.
a carboxylic acid
C.
a ketone
D.
a mixture of equal amounts of aldehyde and carboxylic acid


26.
The major product of this reaction is:
A.
an ether
B.
a mixture of unequal amounts of two different alkenes
C.
a ketone
D.
a mixture of equal amounts of two different alkenes


27.
The major product of this reaction is:
A.
an ether
B.
a mixture of unequal amounts of two different alkenes
C.
a ketone
D.
a mixture of equal amounts of two different alkenes


28.
The addition of a few drops of potassium dichromate solution (orange) to _______ produces a green solution.
A.
t-butyl alcohol
B.
ethyl methyl ether
C.
pentane
D.
1-butanol


29.
An unknown compound may be:
 
I.
cyclohexanol
II.
toluene
III.
ethyl methyl ether
The compound is neutral to litmus paper; it does not turn blue litmus paper red or red litmus paper blue. Identify the compound.
A.
It could be I or II
B.
It could be II or III
C.
It could be I, II, or III
D.
It must be I


30.
Many apply 2-propanol (rubbing alcohol) to the skin to lower a fever. Alcohols such as 1-decanol or 2-decanol are not useful for this purpose. Why does 2-propanol cool skin but the other two alcohols do not?
A.
Only 2-propanol evaporates rapidly from the skin surface, removing heat and creating a cooling effect.
B.
1-Decanol and 2-decanol are much higher molecular weight compounds than 1-propanol and are, therefore, much more volatile, which results in less heat removed from the skin surface.
C.
2-Propanol is a lower-molecular-weight compound and is, therefore, less volatile. Consequently, it evaporates more rapidly from the skin surface, removing heat and creating a cooling effect.
D.
1-Decanol and 2-decanol are much lower molecular weight compounds than 2-propanol. Therefore, they are less volatile and will not remove as much heat from the skin.


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