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 the following alcohol using IUPAC systematic nomenclature:
OH
CH₃-CH-CH₂-CH₃
|
CH₃
Correct Answer: 3-methylpentan-2-ol
Rationale: The parent chain must be the longest continuous chain containing the -OH
group (5 carbons = pentane). Numbering gives the -OH the lowest possible number, so
numbering starts from the right. The hydroxyl group is on carbon 2, with a methyl
substituent on carbon 3.
Question 2
Name the following alcohol using IUPAC systematic nomenclature:
OH (attached to a cyclobutane ring)
Correct Answer: Cyclobutanol
Rationale: For cyclic alcohols, the parent chain is the ring (cyclobutane), and the suffix -
ol is added. The -OH carbon is always carbon 1 by definition, so no number is needed .
, Question 3
Name the following alcohol using IUPAC systematic nomenclature:
OH
CH₂=CH-CH₂-CH₂OH
Correct Answer: 3-buten-1-ol
Rationale: The parent chain must include both the -OH group and the double bond.
The chain is 4 carbons long (butene) and numbering gives the -OH the lowest possible
number (carbon 1), so the double bond falls at carbon 3 .
Question 4
Name the following alcohol using IUPAC systematic nomenclature:
OH (benzene ring with OH at C1, methyl at C3, nitro at C5)
Correct Answer: 3-methyl-5-nitrophenol
Rationale: For substituted phenols, the -OH is at carbon 1 by definition. Numbering
proceeds around the ring to give substituents the lowest possible numbers. Methyl at
C3 and nitro at C5.
Question 5
Classify each of the following alcohols as primary (1°), secondary (2°), or tertiary (3°):
a. 2-methyl-1-propanol
b. Cyclopentanol
c. 2-butene-1-ol
d. 3,5-dinitrophenol
Correct Answer:
a. Primary
Questions and Answers/ Portage Chem
219 Module 5 Review/ Principles of
Organic Chemistry with Lab
Section 1: Alcohol Nomenclature and Classification
Question 1
Name the following alcohol using IUPAC systematic nomenclature:
OH
CH₃-CH-CH₂-CH₃
|
CH₃
Correct Answer: 3-methylpentan-2-ol
Rationale: The parent chain must be the longest continuous chain containing the -OH
group (5 carbons = pentane). Numbering gives the -OH the lowest possible number, so
numbering starts from the right. The hydroxyl group is on carbon 2, with a methyl
substituent on carbon 3.
Question 2
Name the following alcohol using IUPAC systematic nomenclature:
OH (attached to a cyclobutane ring)
Correct Answer: Cyclobutanol
Rationale: For cyclic alcohols, the parent chain is the ring (cyclobutane), and the suffix -
ol is added. The -OH carbon is always carbon 1 by definition, so no number is needed .
, Question 3
Name the following alcohol using IUPAC systematic nomenclature:
OH
CH₂=CH-CH₂-CH₂OH
Correct Answer: 3-buten-1-ol
Rationale: The parent chain must include both the -OH group and the double bond.
The chain is 4 carbons long (butene) and numbering gives the -OH the lowest possible
number (carbon 1), so the double bond falls at carbon 3 .
Question 4
Name the following alcohol using IUPAC systematic nomenclature:
OH (benzene ring with OH at C1, methyl at C3, nitro at C5)
Correct Answer: 3-methyl-5-nitrophenol
Rationale: For substituted phenols, the -OH is at carbon 1 by definition. Numbering
proceeds around the ring to give substituents the lowest possible numbers. Methyl at
C3 and nitro at C5.
Question 5
Classify each of the following alcohols as primary (1°), secondary (2°), or tertiary (3°):
a. 2-methyl-1-propanol
b. Cyclopentanol
c. 2-butene-1-ol
d. 3,5-dinitrophenol
Correct Answer:
a. Primary
