Chem 219 Module 5 Problem Set
Questions and Answers/ Portage Chem
219 Module 5 Review/ Principles of
Organic Chemistry with Lab
SECTION 1: ALCOHOL NOMENCLATURE AND
CLASSIFICATION
Question 1
Name each of the following alcohols using IUPAC systematic nomenclature:
A. Structure with OH on carbon 1 of a 3-carbon chain with a methyl on carbon 2
B. Cyclic 5-carbon ring with OH attached
C. 4-carbon chain with double bond between carbons 2-3 and OH on carbon 1
D. Benzene ring with OH and two nitro groups at positions 3 and 5
Answers:
A. 2-methyl-1-propanol (or 2-methylpropan-1-ol)
B. Cyclopentanol
C. 2-buten-1-ol (or E-2-buten-1-ol)
D. 3,5-dinitrophenol
Rationale: For alcohol nomenclature, identify the parent chain containing the -OH
group, number to give the -OH the lowest possible number, and use the "-ol" suffix. For
phenols, the -OH is assumed at position 1 on the benzene ring.
Question 2
,Classify each of the following alcohols as primary, secondary, or tertiary:
A. CH₃CH₂CH₂OH
B. (CH₃)₂CHCH₂OH
C. CH₃CH(OH)CH₃
D. (CH₃)₃COH
Answers:
A. Primary
B. Primary
C. Secondary
D. Tertiary
Rationale: A primary alcohol has the -OH attached to a carbon bonded to only one
other carbon. Secondary has the -OH carbon bonded to two carbons. Tertiary has the -
OH carbon bonded to three carbons.
Question 3
What is the functional group in an alcohol?
A. -COOH
B. -OH
C. -NH₂
D. -CHO
Correct Answer: B. -OH
Rationale: Alcohols contain a hydroxyl (-OH) group bonded to a saturated carbon
atom.
Question 4
Which of the following is a primary alcohol?
,A. CH₃CH₂OH
B. (CH₃)₂CHOH
C. CH₃CH₂CH₂OH
D. Both A and C
Correct Answer: D. Both A and C
Rationale: Both ethanol (CH₃CH₂OH) and 1-propanol (CH₃CH₂CH₂OH) have the -OH
group attached to a carbon bonded to only one other carbon, making them primary
alcohols.
Question 5
Alcohols can act as weak acids or weak bases depending on their environment. This
property is called:
A. Isomerism
B. Amphoteric
C. Catenation
D. Hybridization
Correct Answer: B. Amphoteric
Rationale: Alcohols are amphoteric substances because they can act as weak acids
(donating the O-H proton as H⁺) or as weak bases (accepting H⁺ using a lone pair on the
oxygen atom).
Question 6
The product formed when a primary alcohol is oxidized is initially a(n):
A. Ketone
B. Aldehyde
C. Carboxylic acid
D. Alkene
, Correct Answer: B. Aldehyde
Rationale: Primary alcohols oxidize first to aldehydes, then can further oxidize to
carboxylic acids.
SECTION 2: ETHER NOMENCLATURE AND PROPERTIES
Question 7
Name each of the following ethers using IUPAC systematic nomenclature:
A. (CH₃)₂CHOCH₃
B. CH₃CH₂CH₂OCH₂CH₃
C. Three-membered cyclic ether (C₂H₄O)
D. C₆H₅OCH₃
Answers:
A. Isopropyl methyl ether (2-methoxypropane)
B. 3-methoxypentane
C. Oxacyclobutane (or epoxide/oxirane for three-membered ring)
D. Anisole (methoxybenzene or methyl phenyl ether)
Rationale: Ethers can be named using common names (list alkyl groups alphabetically +
"ether") or IUPAC system (smaller group as alkoxy substituent).
Question 8
Name the crown ether shown below.
Answer: [15]crown-5
Rationale: Crown ether nomenclature follows the pattern "[x]crown-y", where "x" is the
total number of atoms in the ring, and "y" represents the number of oxygen atoms.
Questions and Answers/ Portage Chem
219 Module 5 Review/ Principles of
Organic Chemistry with Lab
SECTION 1: ALCOHOL NOMENCLATURE AND
CLASSIFICATION
Question 1
Name each of the following alcohols using IUPAC systematic nomenclature:
A. Structure with OH on carbon 1 of a 3-carbon chain with a methyl on carbon 2
B. Cyclic 5-carbon ring with OH attached
C. 4-carbon chain with double bond between carbons 2-3 and OH on carbon 1
D. Benzene ring with OH and two nitro groups at positions 3 and 5
Answers:
A. 2-methyl-1-propanol (or 2-methylpropan-1-ol)
B. Cyclopentanol
C. 2-buten-1-ol (or E-2-buten-1-ol)
D. 3,5-dinitrophenol
Rationale: For alcohol nomenclature, identify the parent chain containing the -OH
group, number to give the -OH the lowest possible number, and use the "-ol" suffix. For
phenols, the -OH is assumed at position 1 on the benzene ring.
Question 2
,Classify each of the following alcohols as primary, secondary, or tertiary:
A. CH₃CH₂CH₂OH
B. (CH₃)₂CHCH₂OH
C. CH₃CH(OH)CH₃
D. (CH₃)₃COH
Answers:
A. Primary
B. Primary
C. Secondary
D. Tertiary
Rationale: A primary alcohol has the -OH attached to a carbon bonded to only one
other carbon. Secondary has the -OH carbon bonded to two carbons. Tertiary has the -
OH carbon bonded to three carbons.
Question 3
What is the functional group in an alcohol?
A. -COOH
B. -OH
C. -NH₂
D. -CHO
Correct Answer: B. -OH
Rationale: Alcohols contain a hydroxyl (-OH) group bonded to a saturated carbon
atom.
Question 4
Which of the following is a primary alcohol?
,A. CH₃CH₂OH
B. (CH₃)₂CHOH
C. CH₃CH₂CH₂OH
D. Both A and C
Correct Answer: D. Both A and C
Rationale: Both ethanol (CH₃CH₂OH) and 1-propanol (CH₃CH₂CH₂OH) have the -OH
group attached to a carbon bonded to only one other carbon, making them primary
alcohols.
Question 5
Alcohols can act as weak acids or weak bases depending on their environment. This
property is called:
A. Isomerism
B. Amphoteric
C. Catenation
D. Hybridization
Correct Answer: B. Amphoteric
Rationale: Alcohols are amphoteric substances because they can act as weak acids
(donating the O-H proton as H⁺) or as weak bases (accepting H⁺ using a lone pair on the
oxygen atom).
Question 6
The product formed when a primary alcohol is oxidized is initially a(n):
A. Ketone
B. Aldehyde
C. Carboxylic acid
D. Alkene
, Correct Answer: B. Aldehyde
Rationale: Primary alcohols oxidize first to aldehydes, then can further oxidize to
carboxylic acids.
SECTION 2: ETHER NOMENCLATURE AND PROPERTIES
Question 7
Name each of the following ethers using IUPAC systematic nomenclature:
A. (CH₃)₂CHOCH₃
B. CH₃CH₂CH₂OCH₂CH₃
C. Three-membered cyclic ether (C₂H₄O)
D. C₆H₅OCH₃
Answers:
A. Isopropyl methyl ether (2-methoxypropane)
B. 3-methoxypentane
C. Oxacyclobutane (or epoxide/oxirane for three-membered ring)
D. Anisole (methoxybenzene or methyl phenyl ether)
Rationale: Ethers can be named using common names (list alkyl groups alphabetically +
"ether") or IUPAC system (smaller group as alkoxy substituent).
Question 8
Name the crown ether shown below.
Answer: [15]crown-5
Rationale: Crown ether nomenclature follows the pattern "[x]crown-y", where "x" is the
total number of atoms in the ring, and "y" represents the number of oxygen atoms.
