Question 1

What is the approximate H-S-C bond angle in methanethiol?

Accepted Answer

A)  90° 
B)  124.6° 
C)  100.3° 
D)  180° 
A)  90° 
B)  124.6° 
C)  100.3° 
D)  180°

Question 2

In which class of compounds is the carbon at the functional group most highly oxidized?

Accepted Answer

A)  alcohols 
B)  aldehydes 
C)  carboxylic acids 
D)  ketones 
A)  alcohols 
B)  aldehydes 
C)  carboxylic acids 
D)  ketones

Question 3

What is the common name of the smallest cyclic ether?

Accepted Answer

A)  ethylene oxide 
B)  methylene oxide 
C)  tetrahydrofuran 
D)  methoxycyclopentane 
A)  ethylene oxide 
B)  methylene oxide 
C)  tetrahydrofuran 
D)  methoxycyclopentane

Question 4

What is the common name of the following compound?

Accepted Answer

A)  isobutyl mercaptan 
B)  sec-butyl mercaptan 
C)  2-methyl-1-propanethiol 
D)  propyl mercaptan 
A)  isobutyl mercaptan 
B)  sec-butyl mercaptan 
C)  2-methyl-1-propanethiol 
D)  propyl mercaptan

Question 5

What is the IUPAC name of the following compound?

Accepted Answer

A)  cyclohexyl ethyl ether 
B)  ethyl cyclohexyl ether 
C)  ethoxycyclohexane 
D)  cyclohexoxyethane 
A)  cyclohexyl ethyl ether 
B)  ethyl cyclohexyl ether 
C)  ethoxycyclohexane 
D)  cyclohexoxyethane

Question 6

What is the approximate C-O-C bond angle in the cyclic ether ethylene oxide, C2H4O?

Accepted Answer

A)  60° 
B)  90° 
C)  109° 
D)  120° 
A)  60° 
B)  90° 
C)  109° 
D)  120°

Question 7

Which of the following alcohols has the lowest boiling point?

Accepted Answer

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

Question 8

What are the positions of the ethyl and hydroxyl groups in cis-3-ethylcyclohexanol?

Accepted Answer

A)  hydroxyl group: position 3 and ethyl group: position 1 
B)  hydroxyl group: position 1 and ethyl group: position 1. 
C)  hydroxyl group: position 3 and ethyl group: position 2 
D)  hydroxyl group: position 1 and ethyl group: position 1 
A)  hydroxyl group: position 3 and ethyl group: position 1 
B)  hydroxyl group: position 1 and ethyl group: position 1. 
C)  hydroxyl group: position 3 and ethyl group: position 2 
D)  hydroxyl group: position 1 and ethyl group: position 1

Question 9

Which of the following structures represents 4-methylcyclohexanol?

Accepted Answer

A)    
B)    
C)    
D)    
A)    
B)    
C)    
D)

Question 10

Which of the following alcohols is used as an oxygenate additive in gasoline for conventional road vehicles?

Accepted Answer

A)  ethanol 
B)  isopropanol 
C)  methanol 
D)  phenol 
A)  ethanol 
B)  isopropanol 
C)  methanol 
D)  phenol

Question 11

Which of the following is the IUPAC name for the ether commonly called ethyl methyl ether?

Accepted Answer

A)  ethoxymethane 
B)  ethoxyethane 
C)  methoxymethane 
D)  methoxyethane 
A)  ethoxymethane 
B)  ethoxyethane 
C)  methoxymethane 
D)  methoxyethane

Question 12

Which of the given products can be obtained from the reaction of the following alcohol with sodium dichromate in aqueous sulfuric acid?

Accepted Answer

A)    
B)    
C)    
D)    
A)    
B)    
C)    
D)

Question 13

Which of the following alcohols can be oxidized to aldehydes in carefully controlled experimental conditions?

Accepted Answer

A)  1° alcohols 
B)  2° alcohols 
C)  both 1° and 2° alcohols 
D)  both 2° and 3° alcohols 
A)  1° alcohols 
B)  2° alcohols 
C)  both 1° and 2° alcohols 
D)  both 2° and 3° alcohols

Question 14

Which of the following is true of the hydration-dehydration equilibrium that exists between alcohols and alkenes under aqueous acidic conditions?

Accepted Answer

A)  It lies so far in one direction that it can only be used for the preparation of alcohols. 
B)  It lies so far in one direction that it can only be used for the preparation of alkenes. 
C)  Reaction conditions can be adjusted so that the equilibrium can be used to prepare either alcohols or alkenes in high yields. 
D)  It is not useful for the preparation of either alcohols or alkenes. 
A)  It lies so far in one direction that it can only be used for the preparation of alcohols. 
B)  It lies so far in one direction that it can only be used for the preparation of alkenes. 
C)  Reaction conditions can be adjusted so that the equilibrium can be used to prepare either alcohols or alkenes in high yields. 
D)  It is not useful for the preparation of either alcohols or alkenes.

Question 15

Which of the following statements is true of the hydroxyl functional groups in 1,3-butanediol?

Accepted Answer

A)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon. 
B)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon. 
C)  Both the hydroxyl groups are bonded to a 1° carbon each. 
D)  Neither of the hydroxyl groups is bonded to a 1° carbon. 
A)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 2° carbon. 
B)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon. 
C)  Both the hydroxyl groups are bonded to a 1° carbon each. 
D)  Neither of the hydroxyl groups is bonded to a 1° carbon.

Question 16

Which of the following statements is true of the hydroxyl functional groups in 2,3-butanediol?

Accepted Answer

A)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon. 
B)  Both the hydroxyl groups are bonded to a 2° carbon each. 
C)  Both the hydroxyl groups are bonded to a 3° carbon each. 
D)  None of these is true. 
A)  One hydroxyl group is bonded to a 1° carbon, and the other hydroxyl group is bonded to a 3° carbon. 
B)  Both the hydroxyl groups are bonded to a 2° carbon each. 
C)  Both the hydroxyl groups are bonded to a 3° carbon each. 
D)  None of these is true.

Question 17

Which of the following statements is true of the products formed by the dehydration of trans-4-methylcyclohexanol?

Accepted Answer

A)  The only product formed is 4-methylcyclohexene. 
B)  The only product formed is 5-methylcyclohexene. 
C)  The major product is 4-methylcyclohexene, and the minor product is 5-methylcyclohexene. 
D)  The major product is 5-methylcyclohexene, and the minor product is 4-methylcyclohexene. 
A)  The only product formed is 4-methylcyclohexene. 
B)  The only product formed is 5-methylcyclohexene. 
C)  The major product is 4-methylcyclohexene, and the minor product is 5-methylcyclohexene. 
D)  The major product is 5-methylcyclohexene, and the minor product is 4-methylcyclohexene.

Question 18

Suppose you carried out two reactions in sequence. In the first reaction, you hydrated 1-hexene; in the second reaction, you dehydrated the product(s) of the first reaction. Which of the following would be the major final product?

Accepted Answer

A)  1-hexene 
B)  2-hexene 
C)  3-hexene 
D)  2-methyl-3-pentene 
A)  1-hexene 
B)  2-hexene 
C)  3-hexene 
D)  2-methyl-3-pentene

Exam 13: Alcohols, Ethers, and Thiols

What is the approximate H-S-C bond angle in methanethiol?

In which class of compounds is the carbon at the functional group most highly oxidized?

What is the common name of the smallest cyclic ether?

What is the common name of the following compound?

What is the IUPAC name of the following compound?

What is the approximate C-O-C bond angle in the cyclic ether ethylene oxide, C2H4O?

Which of the following alcohols has the lowest boiling point?

What are the positions of the ethyl and hydroxyl groups in cis-3-ethylcyclohexanol?

Which of the following structures represents 4-methylcyclohexanol?

Which of the following alcohols is used as an oxygenate additive in gasoline for conventional road vehicles?

Which of the following is the IUPAC name for the ether commonly called ethyl methyl ether?

Which of the given products can be obtained from the reaction of the following alcohol with sodium dichromate in aqueous sulfuric acid?

Which of the following alcohols can be oxidized to aldehydes in carefully controlled experimental conditions?

Which of the following is true of the hydration-dehydration equilibrium that exists between alcohols and alkenes under aqueous acidic conditions?

Which of the following statements is true of the hydroxyl functional groups in 1,3-butanediol?

Which of the following statements is true of the hydroxyl functional groups in 2,3-butanediol?

Which of the following statements is true of the products formed by the dehydration of trans-4-methylcyclohexanol?

Suppose you carried out two reactions in sequence. In the first reaction, you hydrated 1-hexene; in the second reaction, you dehydrated the product(s) of the first reaction. Which of the following would be the major final product?

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What is the approximate C-O-C bond angle in the cyclic ether ethylene oxide, C₂H₄O?