NESA Chemistry Reactions of Organic Acids and Bases

15 sample questions with marking guides and sample answers · Avg. score: 54%

Q25
2024
SCSA
1 mark
Q25
1 mark

Which of the following can be used to distinguish between butan-2-one and butanal?

A

bromine water

B

acidified potassium permanganate solution

C

hydrochloric acid solution

D

acetic acid solution, with a sulfuric acid catalyst

Reveal Answer
A

bromine water

Bromine water is used to test for unsaturation (carbon-carbon double or triple bonds). Since neither butan-2-one nor butanal contains these bonds, neither will react to decolorize the solution.

B

acidified potassium permanganate solution

Correct Answer

Acidified potassium permanganate is a strong oxidizing agent. It will oxidize butanal (an aldehyde) to butanoic acid, causing the purple solution to turn colorless, but it will not react with butan-2-one (a ketone).

C

hydrochloric acid solution

Hydrochloric acid does not react with either aldehydes or ketones to produce a visible change, making it useless for distinguishing between the two.

D

acetic acid solution, with a sulfuric acid catalyst

Acetic acid with a sulfuric acid catalyst is used for esterification reactions with alcohols. It will not react with either butan-2-one or butanal.

Q18
2024
VCAA
1 mark
Q18
1 mark

Each of the following compounds has a molar mass of 88 g mol188 \text{ g mol}^{-1}.

Which one has the highest boiling point?

A

CH3CH2OCOCH3\text{CH}_3\text{CH}_2\text{OCOCH}_3

B

CH3(CH2)2COOH\text{CH}_3(\text{CH}_2)_2\text{COOH}

C

CH3(CH2)3CH2OH\text{CH}_3(\text{CH}_2)_3\text{CH}_2\text{OH}

D

CH3NH(CH2)2NHCH3\text{CH}_3\text{NH}(\text{CH}_2)_2\text{NHCH}_3

Reveal Answer
A

CH3CH2OCOCH3\text{CH}_3\text{CH}_2\text{OCOCH}_3

Esters cannot form intermolecular hydrogen bonds, resulting in weaker dipole-dipole interactions and a lower boiling point compared to alcohols and carboxylic acids.

B

CH3(CH2)2COOH\text{CH}_3(\text{CH}_2)_2\text{COOH}

Correct Answer

Carboxylic acids can form strong intermolecular hydrogen bonds, often forming stable dimers. This significantly increases their intermolecular forces and gives them the highest boiling point among compounds of similar molar mass.

C

CH3(CH2)3CH2OH\text{CH}_3(\text{CH}_2)_3\text{CH}_2\text{OH}

While alcohols can form hydrogen bonds, they do not form stable dimers like carboxylic acids do, resulting in slightly weaker overall intermolecular forces and a lower boiling point than option B.

D

CH3NH(CH2)2NHCH3\text{CH}_3\text{NH}(\text{CH}_2)_2\text{NHCH}_3

Amines can form hydrogen bonds, but because nitrogen is less electronegative than oxygen, the N-H bond is less polar than the O-H bond. This makes their hydrogen bonds weaker than those in alcohols and carboxylic acids.

Q19
2024
QCAA
Paper 1
1 mark
Q19
1 mark

Esters undergo hydrolysis to form a carboxylic acid and

A

water.

B

an amine.

C

an alcohol.

D

an aldehyde.

Reveal Answer
A

water.

Water is a reactant required to break the ester bond during hydrolysis, not a product of the reaction.

B

an amine.

Amines are produced during the hydrolysis of amides, not esters.

C

an alcohol.

Correct Answer

Ester hydrolysis cleaves the ester bond, converting the carbonyl group into a carboxylic acid and the alkoxy group into an alcohol.

D

an aldehyde.

Aldehydes are not formed during standard ester hydrolysis; the reaction yields a carboxylic acid and an alcohol.

Q4
2021
QCAA
Paper 1
1 mark
Q4
1 mark

The cleaning action of soap is impaired in hard water because the

A

hydrophilic end reacts with calcium ions to form insoluble salts.

B

hydrophobic end reacts with calcium ions to form insoluble salts.

C

hydrophilic end reacts with calcium ions to form insoluble fatty acids.

D

hydrophobic end reacts with calcium ions to form insoluble fatty acids.

Reveal Answer
A

hydrophilic end reacts with calcium ions to form insoluble salts.

Correct Answer

Hard water contains calcium ions (Ca2+Ca^{2+}) which react with the charged hydrophilic carboxylate group (COO-COO^-) of the soap to form insoluble calcium salts, commonly known as scum.

B

hydrophobic end reacts with calcium ions to form insoluble salts.

The hydrophobic end is the non-polar hydrocarbon chain that interacts with grease and oil; it does not react with the metal ions in the water.

C

hydrophilic end reacts with calcium ions to form insoluble fatty acids.

While the reaction occurs at the hydrophilic end, the product is an insoluble salt (calcium carboxylate), not a free fatty acid. Fatty acids are typically formed when soap reacts with an acid.

D

hydrophobic end reacts with calcium ions to form insoluble fatty acids.

The reaction occurs at the charged hydrophilic head, not the hydrophobic tail, and it results in the formation of insoluble salts rather than fatty acids.

Q14
2024
QCAA
Paper 1
1 mark
Q14
1 mark

The question refers to the reactions below.

Reaction 1: CH3CH2OHH+/Cr2O72(heat/reflux)compound X\text{CH}_3\text{CH}_2\text{OH} \xrightarrow{\text{H}^+/\text{Cr}_2\text{O}_7^{2-} (\text{heat/reflux})} \text{compound X}

Reaction 2: compound X+CH3NH2TiCl4(heat>100C)compound Y\text{compound X} + \text{CH}_3\text{NH}_2 \xrightarrow{\text{TiCl}_4 (\text{heat} > 100^\circ\text{C})} \text{compound Y}

Identify compound Y.

A

CH3_3CH2_2CN

B

CH3_3CONHCH3_3

C

CH3_3CH2_2CH2_2NH2_2

D

H2_2NCH(CH3_3)COOH

Reveal Answer
A

CH3_3CH2_2CN

This is a nitrile (propanenitrile). Nitriles are typically synthesized by reacting haloalkanes with cyanide ions, not by reacting oxidation products of alcohols with amines.

B

CH3_3CONHCH3_3

Correct Answer

Reaction 1 oxidizes ethanol to ethanoic acid (CH3extCOOH\text{CH}_3 ext{COOH}) under reflux. Reaction 2 is a condensation reaction where the carboxylic acid reacts with methylamine (CH3extNH2\text{CH}_3 ext{NH}_2) under heat to form an amide, N-methylethanamide.

C

CH3_3CH2_2CH2_2NH2_2

This is a primary amine with three carbons. The reaction sequence does not add carbon atoms to the chain, nor does it reduce a functional group to a primary amine.

D

H2_2NCH(CH3_3)COOH

This is an amino acid (alanine). The reaction produces a simple amide from a carboxylic acid and an amine, not a molecule with both amine and carboxylic acid functional groups on the same carbon.

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.

Q19
2020
QCAA
Paper 1
1 mark
Q19
1 mark

Dispersion forces, hydrogen bonding, disulfide bridges and ionic bonding all contribute to the

A

primary structure of proteins.

B

secondary structure of proteins.

C

tertiary structure of proteins.

D

quaternary structure of proteins.

Reveal Answer
A

primary structure of proteins.

Primary structure refers to the linear sequence of amino acids held together specifically by covalent peptide bonds, not by the various side-chain interactions listed.

B

secondary structure of proteins.

Secondary structure, such as α\alpha-helices and β\beta-sheets, is primarily stabilized by hydrogen bonds between the backbone amide and carbonyl groups, rather than interactions between side chains.

C

tertiary structure of proteins.

Correct Answer

Tertiary structure is the overall three-dimensional shape of a polypeptide, stabilized by interactions between R groups (side chains) including dispersion forces, hydrogen bonds, ionic bonds (salt bridges), and covalent disulfide bridges.

D

quaternary structure of proteins.

Quaternary structure refers specifically to the arrangement of multiple polypeptide subunits; while these forces hold subunits together, the question describes the forces defining the 3D fold of a single chain (tertiary structure).

Q22
2025
VCAA
1 mark
Q22
1 mark

The major organic product formed when propan-1-ol, CH3CH2CH2OHCH_3CH_2CH_2OH, reacts with butanoic acid, CH3CH2CH2COOHCH_3CH_2CH_2COOH, in the presence of sulfuric acid, H2SO4H_2SO_4, is

A

CH3CH2COOCH2CH2CH2CH3CH_3CH_2COOCH_2CH_2CH_2CH_3

B

CH3CH2CH2CH2OCOCH2CH3CH_3CH_2CH_2CH_2OCOCH_2CH_3

C

CH3CH2OCOCH2CH2CH2CH3CH_3CH_2OCOCH_2CH_2CH_2CH_3

D

CH3CH2CH2COOCH2CH2CH3CH_3CH_2CH_2COOCH_2CH_2CH_3

Reveal Answer
A

CH3CH2COOCH2CH2CH2CH3CH_3CH_2COOCH_2CH_2CH_2CH_3

This structure represents butyl propanoate, which would be formed from the reaction of propanoic acid and butan-1-ol, not butanoic acid and propan-1-ol.

B

CH3CH2CH2CH2OCOCH2CH3CH_3CH_2CH_2CH_2OCOCH_2CH_3

This structure is butyl propanoate written in reverse, which is the product of propanoic acid and butan-1-ol.

C

CH3CH2OCOCH2CH2CH2CH3CH_3CH_2OCOCH_2CH_2CH_2CH_3

This structure represents ethyl pentanoate, which would be formed from the esterification of pentanoic acid and ethanol.

D

CH3CH2CH2COOCH2CH2CH3CH_3CH_2CH_2COOCH_2CH_2CH_3

Correct Answer

This is a Fischer esterification reaction. Butanoic acid (4 carbons) reacts with propan-1-ol (3 carbons) to form the ester propyl butanoate, CH3CH2CH2COOCH2CH2CH3CH_3CH_2CH_2COOCH_2CH_2CH_3.

Q13
2023
QCAA
Paper 1
1 mark
Q13
1 mark

Identify the reaction used to produce methanol and triglycerides.

A

oxidation

B

substitution

C

saponification

D

transesterification

Reveal Answer
A

oxidation

Oxidation involves the loss of electrons or the addition of oxygen to a molecule. It is not the reaction mechanism used for exchanging ester groups between triglycerides and alcohols.

B

substitution

While the underlying mechanism is a nucleophilic acyl substitution, this is a broad category. The specific term for the reaction between an ester and an alcohol is transesterification.

C

saponification

Saponification is the base-catalyzed hydrolysis of triglycerides to produce glycerol and fatty acid salts (soap), rather than the reaction involving methanol to exchange ester groups.

D

transesterification

Correct Answer

Transesterification is the reaction where the organic group of an ester is exchanged with the organic group of an alcohol. It is the specific process governing the interconversion between triglycerides plus methanol and methyl esters plus glycerol.

Q13
2024
QCAA
Paper 1
1 mark
Q13
1 mark

The question refers to the reactions below.

Reaction 1: CH3CH2OHH+/Cr2O72(heat/reflux)compound X\text{CH}_3\text{CH}_2\text{OH} \xrightarrow{\text{H}^+/\text{Cr}_2\text{O}_7^{2-} (\text{heat/reflux})} \text{compound X}

Reaction 2: compound X+CH3NH2TiCl4(heat>100C)compound Y\text{compound X} + \text{CH}_3\text{NH}_2 \xrightarrow{\text{TiCl}_4 (\text{heat} > 100^\circ\text{C})} \text{compound Y}

Determine the type of reaction that produced compound X.

A

addition

B

oxidation

C

substitution

D

esterification

Reveal Answer
A

addition

Addition reactions typically involve breaking a π\pi bond in an unsaturated compound (like an alkene) to add atoms. Ethanol is a saturated molecule, so it does not undergo addition.

B

oxidation

Correct Answer

Reaction 1 uses acidified dichromate (Cr2O72\text{Cr}_2\text{O}_7^{2-}), a strong oxidizing agent, to convert a primary alcohol into a carboxylic acid (or aldehyde). This process involves the loss of hydrogen and gain of oxygen, which defines oxidation.

C

substitution

Substitution involves replacing one functional group with another (e.g., replacing OH-\text{OH} with Cl-\text{Cl}). While the group changes, the primary characteristic of this reaction is the increase in the carbon's oxidation state.

D

esterification

Esterification is the reaction between an alcohol and a carboxylic acid to form an ester. Reaction 1 produces the carboxylic acid itself from an alcohol, rather than reacting two molecules to form an ester.

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
2021
QCAA
Paper 1
1 mark
Q2
1 mark

Intra-chain hydrogen bonding between peptide groups occurs in

A

primary protein structures.

B

secondary protein structures.

C

tertiary protein structures.

D

quaternary protein structures.

Reveal Answer
A

primary protein structures.

Primary structure refers to the linear sequence of amino acids connected by covalent peptide bonds, not hydrogen bonds.

B

secondary protein structures.

Correct Answer

Secondary structures, such as the α\alpha-helix, are stabilized by intra-chain hydrogen bonds formed between the carbonyl (C=OC=O) and amide (NHN-H) groups of the peptide backbone.

C

tertiary protein structures.

Tertiary structure is the overall 3D shape determined primarily by interactions between amino acid side chains (R-groups), such as disulfide bridges, hydrophobic interactions, and ionic bonds.

D

quaternary protein structures.

Quaternary structure involves the arrangement of multiple polypeptide subunits held together by inter-chain interactions, rather than intra-chain bonding within a single backbone.

Q10
2022
VCAA
1 mark
Q10
1 mark

The molar mass of glycerol, C3H8O3\text{C}_3\text{H}_8\text{O}_3, is 92.0 g mol192.0 \text{ g mol}^{-1}.

The production of 65.0 g65.0 \text{ g} of C3H8O3\text{C}_3\text{H}_8\text{O}_3 from tripalmitin, C51H98O6\text{C}_{51}\text{H}_{98}\text{O}_6, which is a triglyceride

A

requires 12.7 g12.7 \text{ g} of water.

B

requires 38.2 g38.2 \text{ g} of water.

C

produces 12.7 g12.7 \text{ g} of water.

D

produces 38.2 g38.2 \text{ g} of water.

Reveal Answer
A

requires 12.7 g12.7 \text{ g} of water.

This incorrectly assumes a 1:1 molar ratio of water to glycerol. The hydrolysis of a triglyceride actually requires 3 moles of water per mole of glycerol produced.

B

requires 38.2 g38.2 \text{ g} of water.

Correct Answer

The hydrolysis of a triglyceride requires 3 moles of water to produce 1 mole of glycerol. Producing 0.7065 mol0.7065 \text{ mol} of glycerol (65.0 g/92.0 g mol165.0 \text{ g} / 92.0 \text{ g mol}^{-1}) requires 3×0.7065=2.12 mol3 \times 0.7065 = 2.12 \text{ mol} of water, which has a mass of 38.2 g38.2 \text{ g}.

C

produces 12.7 g12.7 \text{ g} of water.

This option is incorrect because the reaction is a hydrolysis, which consumes water rather than producing it. Additionally, the mass calculated assumes an incorrect 1:1 molar ratio.

D

produces 38.2 g38.2 \text{ g} of water.

While the mass of water is calculated correctly, the hydrolysis of a triglyceride consumes water as a reactant; it does not produce it.

Q25
2023
SCSA
1 mark
Q25
1 mark

Which of the following statements best differentiates the cleaning action of soaps and detergents?

A

Soaps contain a long, non-polar hydrocarbon tail, whereas detergents contain a carboxylate head that dissolves in grease.

B

Detergents form micelles on agitation, whereas the anionic head of soap dissolves in grease.

C

Detergents do not form precipitates with divalent ions found in water, whereas soaps will precipitate out in similar conditions.

D

Soaps contain a sulfonate group that dissolves in water, whereas detergents contain a carboxylate group that dissolves in water.

Reveal Answer
A

Soaps contain a long, non-polar hydrocarbon tail, whereas detergents contain a carboxylate head that dissolves in grease.

Both soaps and detergents have non-polar hydrocarbon tails that dissolve in grease, and polar heads that dissolve in water, not grease.

B

Detergents form micelles on agitation, whereas the anionic head of soap dissolves in grease.

Both soaps and detergents form micelles upon agitation, and their anionic heads are hydrophilic, meaning they dissolve in water rather than grease.

C

Detergents do not form precipitates with divalent ions found in water, whereas soaps will precipitate out in similar conditions.

Correct Answer

The key functional difference is that soaps form insoluble precipitates (scum) with calcium and magnesium ions in hard water, whereas detergents remain soluble and effective.

D

Soaps contain a sulfonate group that dissolves in water, whereas detergents contain a carboxylate group that dissolves in water.

This statement reverses the functional groups; soaps contain carboxylate groups, while synthetic detergents typically contain sulfonate groups.

Q2
2023
SCSA
1 mark
Q2
1 mark

Which of the following formulae represents an amide?

A

CH3CH(NH2)CH3\text{CH}_3\text{CH(NH}_2\text{)CH}_3

B

CH3COOCH3\text{CH}_3\text{COOCH}_3

C

CH3CONHCH3\text{CH}_3\text{CONHCH}_3

D

CH3COCH2NH2\text{CH}_3\text{COCH}_2\text{NH}_2

Reveal Answer
A

CH3CH(NH2)CH3\text{CH}_3\text{CH(NH}_2\text{)CH}_3

This formula represents an amine, as it contains an amino group (-NH2\text{-NH}_2) attached to an alkyl chain rather than a carbonyl group.

B

CH3COOCH3\text{CH}_3\text{COOCH}_3

This formula represents an ester, which is characterized by the -COO-\text{-COO-} functional group linking two alkyl groups.

C

CH3CONHCH3\text{CH}_3\text{CONHCH}_3

Correct Answer

This formula represents an amide, which is characterized by a carbonyl group (-C=O\text{-C=O}) directly bonded to a nitrogen atom (-NH-\text{-NH-}).

D

CH3COCH2NH2\text{CH}_3\text{COCH}_2\text{NH}_2

This formula represents a compound with both a ketone (-CO-\text{-CO-}) and an amine (-NH2\text{-NH}_2) group, but they are separated by a carbon atom and not directly bonded to form an amide.

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