NESA Chemistry Nomenclature

15 sample questions with marking guides and sample answers · Avg. score: 54.7%

Q17
2025
SCSA
1 mark
Q17
1 mark

Which of the following is the IUPAC name for an isomer of propyl butanoate?

A

methyl pentanoate

B

heptanoic acid

C

6-methylpentanoic acid

D

3-propylbutanoic acid

Reveal Answer
A

methyl pentanoate

Methyl pentanoate contains 6 carbons (11 from methyl + 55 from pentanoate), whereas propyl butanoate contains 7 carbons (33 from propyl + 44 from butanoate). Isomers must have the same molecular formula.

B

heptanoic acid

Correct Answer

Propyl butanoate is an ester with the formula C7H14O2C_7H_{14}O_2 (3+4=73+4=7 carbons). Heptanoic acid is a carboxylic acid with the same formula C7H14O2C_7H_{14}O_2. Esters and carboxylic acids with the same number of carbon atoms are functional isomers.

C

6-methylpentanoic acid

This name is invalid because a pentanoic acid chain only has 5 carbons, so a substituent cannot be at position 6. Furthermore, a methyl pentanoic acid derivative would only have 6 carbons total, not the required 7.

D

3-propylbutanoic acid

Although a structure constructed from this name would have 7 carbons, '3-propylbutanoic acid' is not a valid IUPAC name. The propyl group would extend the longest carbon chain, making the correct parent name hexanoic acid (specifically 3-methylhexanoic acid).

Q8
2023
NESA
1 mark
Q8
1 mark

How many structural isomers have the molecular formula C3H6F2\text{C}_3\text{H}_6\text{F}_2?

A

2

B

3

C

4

D

5

Reveal Answer
A

2

Incorrect. There are more than 2 structural isomers; this answer likely only accounts for the geminal isomers (both fluorines on the same carbon).

B

3

Incorrect. There are more than 3 structural isomers; this answer likely misses one of the possible arrangements, such as 1,3-difluoropropane.

C

4

Correct Answer

Correct. There are exactly 4 structural isomers for C3H6F2\text{C}_3\text{H}_6\text{F}_2: 1,1-difluoropropane, 2,2-difluoropropane, 1,2-difluoropropane, and 1,3-difluoropropane.

D

5

Incorrect. There are only 4 unique structural isomers; any fifth arrangement would just be a duplicate of one of the four due to the symmetry of the propane chain.

Q16
2024
SCSA
1 mark
Q16
1 mark

How many straight-chain structural isomers have the formula C4H9BrC_4H_9Br?

A

one

B

two

C

three

D

four

Reveal Answer
A

one

Incorrect. There is more than one unique position on a straight four-carbon chain where the bromine atom can be attached.

B

two

Correct Answer

Correct. There are exactly two straight-chain isomers: 1-bromobutane (bromine on an end carbon) and 2-bromobutane (bromine on an inner carbon).

C

three

Incorrect. Attaching the bromine to the third carbon simply creates 2-bromobutane again, just numbered from the opposite end of the chain.

D

four

Incorrect. While there are four total structural isomers for C4H9BrC_4H_9Br, two of them have branched carbon chains (1-bromo-2-methylpropane and 2-bromo-2-methylpropane), leaving only two straight-chain isomers.

Q4
2020
SCSA
1 mark
Q4
1 mark

The number of possible isomers of C2H2F2\text{C}_2\text{H}_2\text{F}_2 is

A

1

B

2

C

3

D

4

Reveal Answer
A

1

Incorrect. This underestimates the number of isomers. The fluorine atoms can be arranged on the same carbon or different carbons, creating multiple isomers.

B

2

Incorrect. This only accounts for the two structural isomers (1,1-difluoroethene and 1,2-difluoroethene) but misses the geometric (cis-trans) isomers of 1,2-difluoroethene.

C

3

Correct Answer

Correct. There are three isomers in total: 1,1-difluoroethene, cis-1,2-difluoroethene, and trans-1,2-difluoroethene.

D

4

Incorrect. This overestimates the number of isomers. Only three distinct structural and geometric arrangements are possible for C2H2F2\text{C}_2\text{H}_2\text{F}_2.

Q20
2024
VCAA
1 mark
Q20
1 mark

Consider the structural isomers of C5H10O\text{C}_5\text{H}_{10}\text{O} that are aldehydes.

Which one of the following statements is correct?

A

There are three isomers.

B

There is one isomer with an ethyl side branch.

C

There are two isomers that have one methyl side branch.

D

Each isomer has a functional group on the second carbon atom.

Reveal Answer
A

There are three isomers.

There are actually four structural isomers of C5H10O\text{C}_5\text{H}_{10}\text{O} that are aldehydes: pentanal, 2-methylbutanal, 3-methylbutanal, and 2,2-dimethylpropanal.

B

There is one isomer with an ethyl side branch.

There are no isomers with an ethyl side branch. If you try to place an ethyl group on a 3-carbon aldehyde chain, the longest chain containing the aldehyde group becomes 4 carbons long, making it a methyl branch instead (e.g., 2-methylbutanal).

C

There are two isomers that have one methyl side branch.

Correct Answer

This is correct because there are exactly two isomers with a single methyl branch: 2-methylbutanal and 3-methylbutanal.

D

Each isomer has a functional group on the second carbon atom.

By definition, the aldehyde functional group (-CHO) is always located at the end of the carbon chain, which is designated as the first carbon atom (C1), not the second.

Q7
2020
VCAA
1 mark
Q7
1 mark

How many structural isomers have the molecular formula C3H6BrCl\text{C}_3\text{H}_6\text{BrCl}?

A

4

B

5

C

6

D

7

Reveal Answer
A

4

This is incorrect because there are more than 4 structural isomers. This answer likely misses one of the positional combinations of the halogens on the propane chain.

B

5

Correct Answer

This is correct. The five structural isomers are 1-bromo-1-chloropropane, 1-bromo-2-chloropropane, 1-bromo-3-chloropropane, 2-bromo-1-chloropropane, and 2-bromo-2-chloropropane.

C

6

This is incorrect because it overcounts the number of structural isomers. There are exactly 5 unique positional combinations for one bromine and one chlorine atom on a propane chain.

D

7

This is incorrect because it overcounts the number of structural isomers. Stereoisomers (enantiomers) are not counted when specifically asking for structural isomers.

Q14
2023
SCSA
1 mark
Q14
1 mark

Identify the type of structure from the following description:

An organic molecule containing a carboxylic acid group, a side chain and an amine group bound to the same carbon atom.

A

polyester

B

soap

C

α\alpha-amino acid

D

biodiesel

Reveal Answer
A

polyester

Polyesters are polymers made of repeating ester linkages, not individual molecules containing both amine and carboxylic acid groups on the same carbon.

B

soap

Soaps are typically sodium or potassium salts of long-chain fatty acids and do not contain an amine group.

C

α\alpha-amino acid

Correct Answer

This perfectly describes an α\alpha-amino acid, which consists of a central α\alpha-carbon bonded to an amino group (NH2-NH_2), a carboxyl group (COOH-COOH), and a variable side chain.

D

biodiesel

Biodiesel consists of mono-alkyl esters of long-chain fatty acids, which lack the amine group mentioned in the description.

Q13
2023
VCAA
1 mark
Q13
1 mark

Which molecule can exist as both a cis and a trans isomer?

A

CH2CBrCl\text{CH}_2\text{CBrCl}

B

CH3CHBrCl\text{CH}_3\text{CHBrCl}

C

CH3CHCHCl\text{CH}_3\text{CHCHCl}

D

(CH3)2CCCl2(\text{CH}_3)_2\text{CCCl}_2

Reveal Answer
A

CH2CBrCl\text{CH}_2\text{CBrCl}

The molecule CH2=CBrCl\text{CH}_2=\text{CBrCl} has two identical hydrogen atoms on one of the double-bonded carbons, which prevents cis-trans isomerism.

B

CH3CHBrCl\text{CH}_3\text{CHBrCl}

The molecule CH3CHBrCl\text{CH}_3\text{CHBrCl} is an alkane with only single bonds, so it cannot exhibit cis-trans isomerism (though it does have enantiomers).

C

CH3CHCHCl\text{CH}_3\text{CHCHCl}

Correct Answer

The molecule CH3CH=CHCl\text{CH}_3\text{CH}=\text{CHCl} has a carbon-carbon double bond where each carbon is attached to two different groups, satisfying the requirements for cis and trans isomers.

D

(CH3)2CCCl2(\text{CH}_3)_2\text{CCCl}_2

The molecule (CH3)2C=CCl2(\text{CH}_3)_2\text{C}=\text{CCl}_2 has identical groups on both carbons of the double bond (two methyls on one, two chlorines on the other), making cis-trans isomerism impossible.

Q21
2022
QCAA
Paper 1
4 marks
Q21a
2 marks

Identify whether 2-bromopropane is a saturated or unsaturated compound. Explain your reasoning.

Reveal Answer

2-bromopropane is saturated because it contains only single bonds.

Marking Criteria
DescriptorMarks

Identifies 2-bromopropane is saturated

1

Indicates 2-bromopropane contains only single bonds

1
Q21b
2 marks

Determine whether 2-bromopropane is a primary, secondary or tertiary halogenoalkane. Explain your reasoning.

Reveal Answer

2-bromopropane is a secondary halogenoalkane, because the carbon that the bromine is attached to two carbon atoms.

Marking Criteria
DescriptorMarks

Determines 2-bromopropane is a secondary halogenoalkane

1

Explains that the bromine (halogen) is bonded to a carbon that is attached to two other carbon atoms

1
Q16
2021
SCSA
1 mark
Q16
1 mark

Two isomeric forms of a saturated hydrocarbon

A

contain different types of atoms.

B

have the same structural formula.

C

have the same molecular formula.

D

react vigorously with one another.

Reveal Answer
A

contain different types of atoms.

Isomers have the same molecular formula, meaning they contain the exact same types and numbers of atoms.

B

have the same structural formula.

Isomers are defined by having different structural formulas (arrangements of atoms) despite having the same molecular formula.

C

have the same molecular formula.

Correct Answer

By definition, isomers are compounds that share the same molecular formula but have different structural arrangements.

D

react vigorously with one another.

Saturated hydrocarbons (alkanes) are generally stable and unreactive, so they do not react vigorously with one another.

Q7
2021
QCAA
Paper 1
1 mark
Q7
1 mark

Identify which molecule is an amide.

A

CH3_3CH2_2CN

B

CH3_3CH2_2NH2_2

C

NH4_4CH3_3COO

D

CH3_3CONHCH3_3

Reveal Answer
A

CH3_3CH2_2CN

This molecule contains a cyano group (CN-CN), making it a nitrile (specifically propanenitrile), not an amide.

B

CH3_3CH2_2NH2_2

This molecule contains an amino group (NH2-NH_2) attached to an alkyl chain, identifying it as an amine (ethylamine). An amide requires a carbonyl group adjacent to the nitrogen.

C

NH4_4CH3_3COO

This is an ammonium salt (ammonium acetate), composed of acetate ions and ammonium ions held together by ionic bonds, rather than the covalent carbonyl-nitrogen bond found in amides.

D

CH3_3CONHCH3_3

Correct Answer

This molecule is an amide (N-methylacetamide) because it contains a carbonyl group (C=OC=O) directly bonded to a nitrogen atom.

Q2
2022
QCAA
Paper 1
1 mark
Q2
1 mark

Structural isomers are compounds with the same molecular formula but a different

A

molar mass.

B

molecular mass.

C

empirical formula.

D

arrangement of atoms.

Reveal Answer
A

molar mass.

Since structural isomers share the same molecular formula, they contain the exact same number of atoms of each element and therefore have identical molar masses.

B

molecular mass.

Molecular mass is determined by the sum of the atomic masses in the molecular formula; since isomers have the same formula, their molecular masses are the same.

C

empirical formula.

The empirical formula represents the simplest ratio of elements; because the molecular formula is identical for isomers, their empirical formulas are also identical.

D

arrangement of atoms.

Correct Answer

Structural isomers are defined as compounds that have the same molecular formula but differ in the connectivity or bonding arrangement of their atoms.

Q23
2023
VCAA
1 mark
Q23
1 mark

Which one of the following is the semi-structural formula of 2-methylpent-1-ene?

A

(CH3)2CCHCH2CH3(\text{CH}_3)_2\text{CCHCH}_2\text{CH}_3

B

(CH3)2CHCH2CHCH2(\text{CH}_3)_2\text{CHCH}_2\text{CHCH}_2

C

CH2C(CH3)CH2CH2CH3\text{CH}_2\text{C(CH}_3\text{)CH}_2\text{CH}_2\text{CH}_3

D

CH2CHCH(CH3)CH2CH3\text{CH}_2\text{CHCH(CH}_3\text{)CH}_2\text{CH}_3

Reveal Answer
A

(CH3)2CCHCH2CH3(\text{CH}_3)_2\text{CCHCH}_2\text{CH}_3

Incorrect. This structure represents 2-methylpent-2-ene, where the double bond is located between the second and third carbon atoms.

B

(CH3)2CHCH2CHCH2(\text{CH}_3)_2\text{CHCH}_2\text{CHCH}_2

Incorrect. This structure represents 4-methylpent-1-ene, where the methyl group is attached to the fourth carbon atom instead of the second.

C

CH2C(CH3)CH2CH2CH3\text{CH}_2\text{C(CH}_3\text{)CH}_2\text{CH}_2\text{CH}_3

Correct Answer

Correct. The formula CH2C(CH3)CH2CH2CH3\text{CH}_2\text{C(CH}_3\text{)CH}_2\text{CH}_2\text{CH}_3 correctly places the double bond at the first carbon and the methyl branch at the second carbon, matching 2-methylpent-1-ene.

D

CH2CHCH(CH3)CH2CH3\text{CH}_2\text{CHCH(CH}_3\text{)CH}_2\text{CH}_3

Incorrect. This structure represents 3-methylpent-1-ene, where the methyl group is attached to the third carbon atom.

Q19
2024
VCAA
1 mark
Q19
1 mark

Which one of the following statements about cyclohexane and benzene is correct?

A

Both have structural isomers that are not cyclic.

B

Both have the same average bond strength between their carbon atoms.

C

Both are members of the same homologous series.

D

Each carbon in cyclohexane has one more valence electron than each carbon in benzene.

Reveal Answer
A

Both have structural isomers that are not cyclic.

Correct Answer

Both molecules have acyclic structural isomers. For example, cyclohexane (C6H12C_6H_{12}) is isomeric with hex-1-ene, and benzene (C6H6C_6H_6) is isomeric with 1,5-hexadiyne.

B

Both have the same average bond strength between their carbon atoms.

Cyclohexane contains only C-C single bonds, whereas benzene has delocalized pi electrons resulting in a carbon-carbon bond order of 1.5, meaning their average bond strengths differ.

C

Both are members of the same homologous series.

Cyclohexane is a cycloalkane (general formula CnH2nC_nH_{2n}) while benzene is an aromatic hydrocarbon (general formula CnH2n6C_nH_{2n-6}), so they belong to different homologous series.

D

Each carbon in cyclohexane has one more valence electron than each carbon in benzene.

Carbon is a Group 14 element and always has exactly four valence electrons, regardless of the molecule it is part of.

Q21
2025
NESA
2 marks
Q21
2 marks

Consider the following organic reaction.

CH3CH2CH2CH3+Br2Reaction condition XCH3CH2CHBrCH3+HBr\text{CH}_3\text{CH}_2\text{CH}_2\text{CH}_3 + \text{Br}_2 \xrightarrow{\text{Reaction condition X}} \text{CH}_3\text{CH}_2\text{CHBrCH}_3 + \text{HBr}

In the space provided, identify reaction condition X and name the organic product.

Reaction condition XIUPAC name of organic product
  
Reveal Answer

Reaction condition XIUPAC name of organic product
UV light2-bromobutane
Marking Criteria
DescriptorMarks

Correctly identifies both the reaction condition AND product

2

Correctly identifies either the reaction condition OR product

1

None of the above

0

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