IUPAC Naming of Organic Compounds
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IUPAC Naming of Organic Compounds — Free MYP5 Chemistry Practice Questions

1QuestionMultiple substituents (di, tri, tetra…)Concept Practice
2 marks~3 minCriterion A
The structural formula below shows a straight-chain alkane with four carbon atoms. A methyl group (CH3\text{CH}_3) is attached to carbon-2 and another methyl group is attached to carbon-3. Each carbon satisfies tetravalency.

(a) Deduce the IUPAC name of this compound. [2]
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Solutions

2QuestionNaming cyclic compounds (basic)Assessment Practice
5 marks~8 minCriterion D
Three isomers of C8H16\text{C}_8\text{H}_{16} have the following experimentally measured boiling points:

1,1-dimethylcyclohexane: 119.7 °C
1,2-cis-dimethylcyclohexane: 129.7 °C
1,3-trans-dimethylcyclohexane: 124.5 °C
a
Draw the structural formula of each isomer using wedge-dash notation to show the position and stereochemistry of the methyl groups. [2]
b
Explain how the position of the methyl groups affects the symmetry and polarity of each isomer. [1]
c
Evaluate which isomer's structure best accounts for the observed order of boiling points, justifying your answer in terms of intermolecular forces. [2]
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Solutions

3QuestionNaming cyclic compounds (basic)Assessment Practice
5 marks~8 minCriterion B
The standard enthalpy of combustion per CH2\text{CH}_2 group for four cycloalkanes is given below.

Cycloalkanecyclopropanecyclobutanecyclopentanecyclohexane
Enthalpy per CH2\text{CH}_2 / kJ mol−1^{-1}−697-697−683-683−664-664−659-659
a
Identify the trend in combustion enthalpy per CH2\text{CH}_2 as ring size increases from cyclopropane to cyclohexane. [1]
b
Deduce the combustion enthalpy per CH2\text{CH}_2 for cycloheptane (C7H14\text{C}_7\text{H}_{14}), showing your reasoning from the data. [2]
c
Justify the trend identified in (a) using Baeyer strain theory, and explain why the values approach a limiting enthalpy as ring size increases. [2]
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4QuestionNaming compounds with functional groups like Alcohols (-ol) and Carboxylic acids (-oic acid)Assessment Practice
5 marks~8 minCriterion C
An unknown organic compound has the molecular formula C3H6O2\text{C}_3\text{H}_6\text{O}_2. Its infrared (IR) spectrum shows a strong, broad absorption at approximately 3300 cm−13300 \ \text{cm}^{-1} and a strong, sharp absorption at approximately 1710 cm−11710 \ \text{cm}^{-1}.

Two students propose different identities for the compound:

Student 1: "The compound is propan-1-ol."
Student 2: "The compound is propanoic acid."
a
Identify the functional groups responsible for each IR absorption band. [2]
b
State the IUPAC name and structural formula of the correct compound. [1]
c
Evaluate both students' claims, explaining why one is supported by the spectral data and the other is not. [2]
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Solutions

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