NESA Chemistry Nomenclature
15 sample questions with marking guides and sample answers · Avg. score: 54.7%
Which of the following is the IUPAC name for an isomer of propyl butanoate?
methyl pentanoate
heptanoic acid
6-methylpentanoic acid
3-propylbutanoic acid
Reveal Answer
methyl pentanoate
Methyl pentanoate contains 6 carbons ( from methyl + from pentanoate), whereas propyl butanoate contains 7 carbons ( from propyl + from butanoate). Isomers must have the same molecular formula.
heptanoic acid
Propyl butanoate is an ester with the formula ( carbons). Heptanoic acid is a carboxylic acid with the same formula . Esters and carboxylic acids with the same number of carbon atoms are functional isomers.
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.
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).
How many structural isomers have the molecular formula ?
2
3
4
5
Reveal Answer
2
Incorrect. There are more than 2 structural isomers; this answer likely only accounts for the geminal isomers (both fluorines on the same carbon).
3
Incorrect. There are more than 3 structural isomers; this answer likely misses one of the possible arrangements, such as 1,3-difluoropropane.
4
Correct. There are exactly 4 structural isomers for : 1,1-difluoropropane, 2,2-difluoropropane, 1,2-difluoropropane, and 1,3-difluoropropane.
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.
How many straight-chain structural isomers have the formula ?
one
two
three
four
Reveal Answer
one
Incorrect. There is more than one unique position on a straight four-carbon chain where the bromine atom can be attached.
two
Correct. There are exactly two straight-chain isomers: 1-bromobutane (bromine on an end carbon) and 2-bromobutane (bromine on an inner carbon).
three
Incorrect. Attaching the bromine to the third carbon simply creates 2-bromobutane again, just numbered from the opposite end of the chain.
four
Incorrect. While there are four total structural isomers for , two of them have branched carbon chains (1-bromo-2-methylpropane and 2-bromo-2-methylpropane), leaving only two straight-chain isomers.
The number of possible isomers of is
1
2
3
4
Reveal Answer
1
Incorrect. This underestimates the number of isomers. The fluorine atoms can be arranged on the same carbon or different carbons, creating multiple isomers.
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.
3
Correct. There are three isomers in total: 1,1-difluoroethene, cis-1,2-difluoroethene, and trans-1,2-difluoroethene.
4
Incorrect. This overestimates the number of isomers. Only three distinct structural and geometric arrangements are possible for .
Consider the structural isomers of that are aldehydes.
Which one of the following statements is correct?
There are three isomers.
There is one isomer with an ethyl side branch.
There are two isomers that have one methyl side branch.
Each isomer has a functional group on the second carbon atom.
Reveal Answer
There are three isomers.
There are actually four structural isomers of that are aldehydes: pentanal, 2-methylbutanal, 3-methylbutanal, and 2,2-dimethylpropanal.
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).
There are two isomers that have one methyl side branch.
This is correct because there are exactly two isomers with a single methyl branch: 2-methylbutanal and 3-methylbutanal.
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.
How many structural isomers have the molecular formula ?
4
5
6
7
Reveal Answer
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.
5
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.
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.
7
This is incorrect because it overcounts the number of structural isomers. Stereoisomers (enantiomers) are not counted when specifically asking for structural isomers.
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.
polyester
soap
-amino acid
biodiesel
Reveal Answer
polyester
Polyesters are polymers made of repeating ester linkages, not individual molecules containing both amine and carboxylic acid groups on the same carbon.
soap
Soaps are typically sodium or potassium salts of long-chain fatty acids and do not contain an amine group.
-amino acid
This perfectly describes an -amino acid, which consists of a central -carbon bonded to an amino group (), a carboxyl group (), and a variable side chain.
biodiesel
Biodiesel consists of mono-alkyl esters of long-chain fatty acids, which lack the amine group mentioned in the description.
Which molecule can exist as both a cis and a trans isomer?
Reveal Answer
The molecule has two identical hydrogen atoms on one of the double-bonded carbons, which prevents cis-trans isomerism.
The molecule is an alkane with only single bonds, so it cannot exhibit cis-trans isomerism (though it does have enantiomers).
The molecule has a carbon-carbon double bond where each carbon is attached to two different groups, satisfying the requirements for cis and trans isomers.
The molecule has identical groups on both carbons of the double bond (two methyls on one, two chlorines on the other), making cis-trans isomerism impossible.
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.
| Descriptor | Marks |
|---|---|
Identifies 2-bromopropane is saturated | 1 |
Indicates 2-bromopropane contains only single bonds | 1 |
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.
| Descriptor | Marks |
|---|---|
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 |
Two isomeric forms of a saturated hydrocarbon
contain different types of atoms.
have the same structural formula.
have the same molecular formula.
react vigorously with one another.
Reveal Answer
contain different types of atoms.
Isomers have the same molecular formula, meaning they contain the exact same types and numbers of atoms.
have the same structural formula.
Isomers are defined by having different structural formulas (arrangements of atoms) despite having the same molecular formula.
have the same molecular formula.
By definition, isomers are compounds that share the same molecular formula but have different structural arrangements.
react vigorously with one another.
Saturated hydrocarbons (alkanes) are generally stable and unreactive, so they do not react vigorously with one another.
Identify which molecule is an amide.
CHCHCN
CHCHNH
NHCHCOO
CHCONHCH
Reveal Answer
CHCHCN
This molecule contains a cyano group (), making it a nitrile (specifically propanenitrile), not an amide.
CHCHNH
This molecule contains an amino group () attached to an alkyl chain, identifying it as an amine (ethylamine). An amide requires a carbonyl group adjacent to the nitrogen.
NHCHCOO
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.
CHCONHCH
This molecule is an amide (N-methylacetamide) because it contains a carbonyl group () directly bonded to a nitrogen atom.
Structural isomers are compounds with the same molecular formula but a different
molar mass.
molecular mass.
empirical formula.
arrangement of atoms.
Reveal Answer
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.
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.
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.
arrangement of atoms.
Structural isomers are defined as compounds that have the same molecular formula but differ in the connectivity or bonding arrangement of their atoms.
Which one of the following is the semi-structural formula of 2-methylpent-1-ene?
Reveal Answer
Incorrect. This structure represents 2-methylpent-2-ene, where the double bond is located between the second and third carbon atoms.
Incorrect. This structure represents 4-methylpent-1-ene, where the methyl group is attached to the fourth carbon atom instead of the second.
Correct. The formula correctly places the double bond at the first carbon and the methyl branch at the second carbon, matching 2-methylpent-1-ene.
Incorrect. This structure represents 3-methylpent-1-ene, where the methyl group is attached to the third carbon atom.
Which one of the following statements about cyclohexane and benzene is correct?
Both have structural isomers that are not cyclic.
Both have the same average bond strength between their carbon atoms.
Both are members of the same homologous series.
Each carbon in cyclohexane has one more valence electron than each carbon in benzene.
Reveal Answer
Both have structural isomers that are not cyclic.
Both molecules have acyclic structural isomers. For example, cyclohexane () is isomeric with hex-1-ene, and benzene () is isomeric with 1,5-hexadiyne.
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.
Both are members of the same homologous series.
Cyclohexane is a cycloalkane (general formula ) while benzene is an aromatic hydrocarbon (general formula ), so they belong to different homologous series.
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.
Consider the following organic reaction.
In the space provided, identify reaction condition X and name the organic product.
| Reaction condition X | IUPAC name of organic product |
|---|---|
Reveal Answer
| Reaction condition X | IUPAC name of organic product |
|---|---|
| UV light | 2-bromobutane |
| Descriptor | Marks |
|---|---|
Correctly identifies both the reaction condition AND product | 2 |
Correctly identifies either the reaction condition OR product | 1 |
None of the above | 0 |