Deck 9: Organic Reactions 2-Alcohols, Ethers, Aldehydes, and Ketones

Question 1

The IUPAC name for the organic compound below is

A) 3-Butanol
B) 2-Butanol
C) Ethyl methyl ether
D) 3-butanethiol

Answer 1

Ethyl methyl ether

Question 2

The common name for CH₃-O-CH₃ is ___.

A) methanal
B) dimethanol
C) ethyl ether
D) dimethyl ether

Answer 2

dimethyl ether

Question 3

The short thiols tend to have a disagreeable odor. Which is a thiol?

A)
B)
C)
D) None of these choices.

Answer 3

Question 4

The compound that is expected to have the highest boiling point is ___.

A) the alcohol produced from methane.
B) the thiol produced from methane.
C) methane.
D) They all boil at the same temperature since methane is the basis for the compounds.

Question 5

Each of these is based on the propane molecule. Which is NOT capable of forming hydrogen bonds to another molecule of the same type?

A) 1-propanol
B) 1-propanethiol
C) 2-propanol
D) propanoic acid

Question 6

Which statement concerning thiols is correct?

A) Thiols are more soluble in water than are alcohols of similar size.
B) The thiols are of lower polarity than disulfides of similar size.
C) A thiol is much less polar than is the parent hydrocarbon.
D) The larger the thiol, the lower the solubility in water.

Question 7

Which of the following molecules can form hydrogen bonds with other molecules of the same type?

A)
B)
C)
D)

Question 8

Which of the following molecules has the highest boiling point?

A)
B)
C)
D)

Question 9

Which of these compounds is a properly named 2° alcohol?

A) 1,3-Propandiol
B) 2-Methyl-3-methyl-3-pentanol
C) 1-Propanol
D) 3-Hexanol

Question 10

The molecule below is ___.

A) butyl methyl ether
B) butyl ether
C) cyclopropyl methyl ether
D) a hemiacetal

Question 11

Which nucleophile, when reacted with 1-bromopropane (CH₃CH₂CH₂Br), would produce an ether?

A) OH^-
B) SH^-
C) I^-
D) ^-OCH₃

Question 12

Which nucleophile, when reacted with 1-bromopropane (CH₃CH₂CH₂Br), would produce an alcohol?

A) OH^-
B) SH^-
C) I^-
D) ^-OCH₃

Question 13

Which nucleophile, when reacted with 1-bromopropane (CH₃CH₂CH₂Br), would produce a thiol?

A) OH^-
B) SH^-
C) I^-
D) ^-OCH₃

Question 14

The product of the nucleophile substitution reaction below is:

A)
B)
C)
D)

Question 15

What is the product of the nucleophilic substitution reaction below?

A)
B)
C)
D)

Question 16

Which compound type is most susceptible to a nucleophillic substitution reaction?

A) hydrocarbon
B) alcohol
C) alkyl halide
D) acid

Question 17

Suppose we were assigned to produce the compound below in the laboratory:
Which of the following would be a good precursor (reactant) for a one-step process?

A)
B)
C)
D)

Question 18

Identify the nucleophile in this reaction.

A) K⁺
B) CH₃CH₂Br
C) CH₃CH₂OH
D) OH^-

Question 19

The product of the nucleophilic substitution reaction below is

A)
B)
C)
D)

Question 20

Provide the product of the following reaction.

A)
B)
C)
D)

Question 21

An important reaction in chemistry is oxidation. Which is an oxidation reaction?

A) An alcohol is converted into a ketone.
B) An oxygen is removed from an alcohol.
C) A double bond between an oxygen and a carbon is broken.
D) A carbonyl group is modified to produce an alcohol.

Question 22

What would be the product if we attempt to oxidize a 3º alcohol?

A) There would be no product, 3º alcohols cannot be oxidized.
B) The product is a ketone.
C) The product is a carboxylic acid.
D) The product is a thiol.

Question 23

The oxidation of methanethiol by I₂ produces what product?

A)
B)
C)
D)

Question 24

Disulfide bonds in a protein have some responsibility for holding the protein molecule in its three-dimensional shape. Which statement is correct when considering disulfide bonds?

A) The disulfide bond is established by an oxidation reaction.
B) The disulfide bond can be broken by a reduction process.
C) Two thiol molecules combine to form a disulfide when treated with the oxidizing agent I₂.
D) All three statements are correct.

Question 25

Which family of compounds is most likely to be relatively unreactive?

A) alcohols
B) ethers
C) sulfides
D) carboxylic acids.

Question 26

Which of the following is the product expected from the reaction below?

A)
B)
C)
D)

Question 27

The organic product expected from the following reaction is:

A)
B)
C)
D)

Question 28

The organic product expected from the following reaction is:

A)
B)
C)
D)

Question 29

The organic product expected from the following reaction is:

A)
B)
C)
D)

Question 30

The organic product expected from the following reaction is:

A)
B)
C)
D)

Question 31

What is the product of the reaction below?

A)
B)
C)
D)

Question 32

What is the major organic product of the following reaction?

A) CH₃CH=CH₂
B) CH₃CH₂CH₂Cr
C) CH₃CH₂CH₃
D) CH₃CH₂CO₂H

Question 33

Aldehydes and ketones both contain a carbonyl carbon atom. They differ in that ___.

A) the carbonyl carbon atom in ketones is attached to two other carbons and in aldehydes, the carbonyl carbon atom is also attached to at least one hydrogen atom.
B) the carbonyl carbon atom in ketones is primary and in aldehydes, the carbonyl is secondary.
C) the carbonyl carbon atom in ketones has a hydrogen attached to it.
D) the carbonyl carbon atom in aldehydes has two carbon atoms attached to it

Question 34

The name for: is ___.

A) ethanol
B) dimethyl ketone
C) dimethyl aldehyde
D) ethanal

Question 35

Which of the following statements is true about aldehydes?

A) Aldehydes have much lower boiling points than alcohols with a similar molecular weight.
B) Aldehydes interact with like molecules through hydrogen bonding.
C) The carbonyl carbon atom in an aldehyde can never be in position number 1.
D) The parent chain of an aldehyde is named by dropping the final "e" from a corresponding alkane and adding "one."

Question 36

To which family of organic compounds does this compound belong?

A) ketone
B) aldehyde
C) acid
D) ether

Question 37

Which compounds contain a C=O?

A) aldehydes and ketones
B) acetals
C) ketals
D) alcohols

Question 38

Shown here is the structure of acetone, a common laboratory solvent:
Another name for acetone is ___.

A) dimethyl aldehyde
B) propanone
C) methyl ethyl aldehyde
D) propanal

Question 39

MEK is the abbreviation for methyl ethyl ketone. It is the common name for a solvent that is sold at hardware and automotive parts stores. Its structure is: What is the IUPAC name for MEK?

A) butanal
B) butanone
C) 2-butanol
D) methyl propanal

Question 40

) Rank the following compounds in order of increasing boiling point (lowest to highest).

A) 2-methyl propane < acetone < 2-propanol
B) 2-methyl propane < 2-propanol < acetone
C) 2-propanol < acetone < 2-methyl propane
D) acetone < 2-methyl propane < 2-propanol

Question 41

What is the IUPAC name of this compound?

A) 4-methy-4-propylbutylaldehyde
B) 4-methylhexanal
C) 4-ethylpentanal
D) 4-ethylpentylaldehyde

Question 42

A reducing agent found in some biological systems is ___.

A) H₂O₂
B) acetaldehyde
C) Pt
D) NADH

Question 43

Which of the following oxidizing agents is necessary to complete the biochemical reaction below?

A) K₂Cr₂O₇
B) NAD⁺
C) Cu²⁺
D) NADH

Question 44

Benedict's solution is added to a test tube containing ethanal. Which of the following statements is correct?

A) ethanal is oxidized to ethanol
B) ethanal is reduced to ethanol
C) ethanal is oxidized to ethanoate ion
D) ethanal is oxidized to propanone

Question 45

If the compound below is oxidized, the resulting product is ___.

A) methane and propane
B) butanal
C) butanoic acid
D) butane

Question 46

Which of the following will be oxidized by Benedict's reagent?

A) ethanol
B) ethanal
C) acetic acid
D) ethane

Question 47

What is the major organic product of the following reaction?

A) CH₃CH=CH₂
B) CH₃CH₂CH₂OH
C) CH₃CH₂CH₃
D) CH₃CH₂COOH

Question 48

What is the expected product when acetaldehyde and hydrogen react in the presence of platinum?

A) ethanol
B) ethanal
C) ethanoic acid
D) propane

Question 49

Which of the following reactant is missing in the reaction below?

A)
B)
C)
D)

Question 50

Which compound is a hemiacetal?

A)
B)
C)
D)

Question 51

If formaldehyde reacts with methanol in an acid solution, the product formed is ___.

A) a new aldehyde
B) an alcohol that is very polar
C) a hemiacetal
D) an acid

Question 52

The structural similarity of acetals and ethers is the presence of ___.

A) C-O-C
B) a carboxylic carbon
C) C-O-H
D) CHO

Question 53

Which of the following is formed when an aldehyde or a ketone undergoes an addition reaction with an alcohol molecule in the presence of an acid catalyst?

A) ester
B) ether
C) hemiacetal
D) alkene

Question 54

This compound, glucose, is important in the chemistry of living things. To which class of compounds does glucose belong?

A) thiol
B) carboxylic acid
C) sulfide
D) hemiacetal

Question 55

Which of the following is the missing reactant in the reaction below?

A)
B)
C)
D)

Question 56

Ethanol is miscible in water, while 1-pentanol has a solubility of just 2.2g/100 mL because solubility in water decreases with increasing alcohol size.

Question 57

Thiols, sulfides and disulfides have high solubility in water.

Question 58

Tertiary alcohols have three carbon atoms attached to carbon that has the OH directly attached.

Question 59

The reaction in which a primary alcohol becomes an aldehyde is an oxidation reaction.

Question 60

When alcohols are dehydrated in the presence of H⁺ and heat, the major product is that formed by removal of -OH from one carbon atom and removal of -H from the neighboring C atom that carries more H atoms.

Question 61

Benedict's solution turns a blue color in the presence of glucose.

Question 62

The reduction of a ketone produces a 2° alcohol.

Question 63

Alcohols and thiols are similar in structure with the thiol possessing a(an) ___ atom in place of the oxygen atom found in alcohols.

Question 64

Dehydration of an alcohol results in the formation of a(n) ___.

Question 65

Ketones and aldehydes contain a ___ carbon.

Question 66

Comparing polar compounds and non-polar compounds, the ___ compounds in this chapter have higher boiling points .

Question 67

Benedict's reagent oxidizes ___ into carboxylic acids.

Question 68

The reduction of a carbon-carbon double bond can be performed by reacting it with ___ while using platinum as a catalyst.

Question 69

The reaction of an aldehyde or ketone with an alcohol results in the formation of a(n) ___.

Question 70

A hemiacetal has a carbon atom attached to a(an) ___ group and an -OC group.

Question 71

The reaction of two alcohol molecules with an aldehyde or ketone in the presence of H⁺ results in the formation of a(an) ___.

Question 72

Sketch and name a thiol with 3-carbon atoms.

Question 73

Sketch and name an ether with 3-carbon atoms.

Question 74

Sketch and name a primary alcohol with 4-carbon atoms.

Question 75

Sketch and name a tertiary alcohol with 4-carbon atoms.

Question 76

Sketch the major organic product of the following:

Question 77

Sketch the major organic product of the following:

Question 78

When oxidized, which thiol produces the disulfide shown below?
CH₃CH₂SSCH₂CH₃?

Question 79

Sketch and name the product formed as a result of oxidation of 2-Propanol.

Question 80

Sketch and name an aldehyde with 4-carbon atoms.