Deck 10: Hydration, Dehydration, and Alcohols

Question 1

In the citric acid cycle that occurs in cells, the fumarate ion (shown below) is hydrated in the presence of an enzyme. For this reaction, only one product is possible.

Answer 1

True

Question 2

Which of the following structures represents 3,3-dimethyl-1-butanol?

A)
B)
C)
D)

Answer 2

Question 3

The following compound cannot be dehydrated to form an alkene.

Answer 3

True

Question 4

What is the major product produced upon hydration of the following alkene?

A)
B)
C)
D)

Question 5

The two molecules listed below have identical properties.

Question 6

The correct structure for 3-hexanol is shown below.

Question 7

Pentane would be more soluble in cyclohexane than 1-pentanol.

Question 8

The -OH group in an alcohol is basic.

Question 9

Which of the following alkenes will produce only one product on hydration?

A)1-pentene
B)2-hexene
C)3-heptene
D)4-octene

Question 10

Which of the following would be made from an alcohol by a dehydration reaction?

A)alkyne
B)alkene
C)alkane
D)alkyl halide

Question 11

What is the correct IUPAC name for the following compound?

A)3-methylpentanol
B)2-ethyl-1-butanol
C)2-ethylbutanol
D)1-ethyl-2-butanol

Question 12

Molecules that are nonsuperimposable mirror images are enantiomers.

Question 13

A baseball glove is a chiral object.

Question 14

Which of the following alcohols is least soluble in water?

A)2-butanol
B)2-heptanol
C)2-pentanol
D)2-hexanol

Question 15

2-Butanol contains a chiral carbon atom.

Question 16

How many products will from when the following substance undergoes dehydration?

A)1
B)2
C)3
D)4
E)This compound can not be dehydrated.

Question 17

Which alcohol is formed by the hydration of 2-methyl-2-pentene?

A)
B)
C)
D)

Question 18

The primary function of an enzyme is catalysis.

Question 19

Which of the following is not a characteristic of an enzyme?

A)can react with both reactant enantiomers
B)increase the speed of reactions
C)proteins involved in biological reactions
D)selectively produce one product
E)All are characteristic of an enzyme.

Question 20

1-Octanol has a larger hydrophobic portion than 1-butanol.

Question 21

When phenol dissolves in water, the solution is

A)basic.
B)acidic.
C)neutral

Question 22

Classify the type of compound shown below.

A)alkene
B)alcohol
C)phenol
D)both a and b

Question 23

Of 1-pentanol, 2-pentanol and 3-pentanol, which compound(s) can yield only a single alkene product when dehydrated?

A)only 1-pentanol
B)both 1-pentanol and 2-pentanol
C)both 1-pentanol and 3-pentanol
D)all of them

Question 24

Which of the following compounds would you expect to be foul smelling?

A)CH₃-CH₂-CH₂-OH
B)CH₃-CH₂-CH₂-SH
C)CH₃-CH₂-CH₂-CH₃
D)HO-CH₂-CH₂-CH₂-OH

Question 25

Which of the following solutions would be neutral?

A)0.10 M NaOH
B)0.10 M CH₃CH₂OH
C)0.10 M HCOOH
D)None of the solutions are neutral.

Question 26

If a carbon atom is chiral, which of the following statements must be true about that carbon?

A)It has four single bonds.
B)It has a double bond and two single bonds.
C)It has two double bonds.
D)Any of these bonding arrangements can be associated with a chiral carbon.

Question 27

Which of the following alcohols has the highest boiling point?

A)
B)
C)
D)

Question 28

How many chiral carbons are present in the following compound?

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

Question 29

Structurally thiols are most closely related to which of the following classes of compounds?

A)alcohols
B)alkenes
C)phenols
D)alkynes

Question 30

Which of the alcohols shown below will dehydrate to produce this alkene?

A)
B)
C)both a and b
D)neither a nor b

Question 31

Which of the following alcohols has the lowest boiling point?

A)1-pentanol
B)1-octanol
C)1-hexanol
D)1-propanol

Question 32

Which of the following best represents hydrogen bonding in methanol?

A)
B)
C)
D)

Question 33

Which of the following is an incorrect IUPAC name?

A)cyclopropanol
B)3-propanol
C)1-propanol
D)4-octanol
E)All of the names are correct as given.

Question 34

Which of the following might be the pH of a solution of phenol in water?

A)11
B)7
C)4
D)9

Question 35

Which of the carbon atoms in the following structure are chiral?

A)carbon atoms: 1 and 5
B)carbon atoms: 3 and 4
C)carbon atoms: 2, 3 and 4
D)carbon atoms: 1, 2, 3, 4, and 5

Question 36

Which of the following explains the fact that there is extensive hydrogen bonding in alcohols but little if any in thiols?

A)Thiols are less soluble in water than alcohols.
B)Sulfur is less electronegative than oxygen.
C)Thiols have lower boiling points than the corresponding alcohols.
D)All of the above explain the difference.

Question 37

In a phenol, which group is the substituent on the benzene ring?

A)-SH
B)-CH=CH₂
C)-CH₂-CH₂-OH
D)-OH

Question 38

Given the compounds 2,3-dimethylpentane and 2,4-dimethylpentane, which of the following is true?

A)only 2,3-dimethylpentane is chiral
B)only 2,4-dimethylpentane is chiral
C)both are chiral
D)neither is chiral

Question 39

Consider the reaction of the following substance with water. Which of the following correctly characterizes this reaction?

A)Two products will be produced with the addition of water.
B)One product will be produced with the addition of water and the appropriate enzyme.
C)One product will be produced with the addition of water.
D)Two products will be produced with the addition of water and the appropriate enzyme.

Question 40

Which of the structures given below represents the enantiomer of the following compound?

A) only
B) only
C)both a and b
D)neither a nor b

Question 41

Examine the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure ___________________ would be the most soluble in water.

Question 42

Consider the following molecules. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure_____________________ could be used to produce an alkene.

Question 43

Classify the substance shown below.

A)alcohol
B)thiol
C)phenol
D)alcohol and thiol
E)thiol and phenol

Question 44

Draw the structure(s) of the dehydration product(s) of the following substance.

Question 45

Draw the product(s) of the hydration of cyclohexene

Question 46

Consider the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure _____________________cannot be dehydrated.

Question 47

Name the following substance.

Question 48

Which of the following is a characteristic of a thiol?

A)contains an atom other than hydrogen, carbon, and oxygen
B)resembles an alcohol in chemical and physical properties
C)capable of hydrogen bonding
D)quite soluble in water
E)both a and b

Question 49

Examine the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure___________________would have the lowest boiling point.

Question 50

Consider the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure ______________________would produce a single product on dehydration.

Question 51

Examine the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure _________________could hydrogen bond to water to the greatest extent.

Question 52

Consider the structure shown below. Circle the chiral carbon atom(s).

Question 53

Examine the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure __________________ would dehydrate to produce and compound with two double bonds.

Question 54

Consider the following molecules. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure ____________________ would not hydrogen bond with water.

Question 55

Consider the following molecules. Fill in the blanks with the appropriate letter (A,B,C,D).
A 0.10 M solution of structure __________________ would be the most likely to have a pH less than 7.

Question 56

Consider the following molecules. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure ____________________ would be classified as a phenol.

Question 57

Consider the following compounds. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure ________________________ would produce a mixture of products on dehydration.

Question 58

Consider the following molecules. Fill in the blanks with the appropriate letter (A,B,C,D).
Structure ______________________ is a thiol.

Question 59

Draw the condensed structural formula and the line bond formula for 1-hexanol and explain how this structure differs from that of 3-hexanol.