NESA Chemistry Alcohols
15 sample questions with marking guides and sample answers · Avg. score: 65.5%
Each of the following compounds has a molar mass of .
Which one has the highest boiling point?
Reveal Answer
Esters cannot form intermolecular hydrogen bonds, resulting in weaker dipole-dipole interactions and a lower boiling point compared to alcohols and carboxylic acids.
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.
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.
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.
An experiment was carried out to determine the enthalpy of combustion of propan-1-ol. Combustion of 557 mg of propan-1-ol increased the temperature of 150 g of water from to .
The enthalpy of combustion is closest to
Reveal Answer
This answer is incorrect and likely results from a calculation error, such as miscalculating the moles of propan-1-ol or the heat absorbed by the water.
This answer is incorrect and may result from using an incorrect molar mass for propan-1-ol (, ) or a rounding error early in the calculation.
First, calculate the heat absorbed by water: . Then, divide by the moles of propan-1-ol () to get , which is closest to .
This answer is incorrect and likely stems from an error in calculating the temperature change () or the heat energy transferred.
Methane, , and methanol, , can both be used to power fuel cells.
Methane and methanol fuel cells produce
the same amount of greenhouse gases and the same number of electrons per mol of fuel reacted.
the same amount of greenhouse gases and a different number of electrons per mol of fuel reacted.
a different amount of greenhouse gases and the same number of electrons per mol of fuel reacted.
a different amount of greenhouse gases and a different number of electrons per mol of fuel reacted.
Reveal Answer
the same amount of greenhouse gases and the same number of electrons per mol of fuel reacted.
While both fuels produce the same amount of greenhouse gases (1 mole of per mole of fuel), they produce a different number of electrons during oxidation.
the same amount of greenhouse gases and a different number of electrons per mol of fuel reacted.
Both fuels contain one carbon atom per molecule, producing 1 mole of per mole of fuel. However, the oxidation state of carbon changes by 8 in methane and 6 in methanol, producing a different number of electrons.
a different amount of greenhouse gases and the same number of electrons per mol of fuel reacted.
This is incorrect because they produce the same amount of greenhouse gases (1 mole of per mole of fuel) and a different number of electrons.
a different amount of greenhouse gases and a different number of electrons per mol of fuel reacted.
This is incorrect because they produce the same amount of greenhouse gases, as both fuels contain exactly one carbon atom per molecule and thus yield the same amount of .
Bioethanol is a renewable energy source made from biomasses such as starch and cellulosic materials. The two-step process for the conversion of starch and cellulose to bioethanol is shown.
| Process | Step 1 | Step 2 | Conversion to glucose | Production process |
|---|---|---|---|---|
| Starch | Enzymatic hydrolysis (-amylase) of starch biomass to form glucose | Fermentation of glucose to form bioethanol (yeast) | Easier | Faster |
| Cellulose | Acid hydrolysis ( at 320 C and 25 MPa) of cellulose biomass to form glucose | Fermentation of glucose to form bioethanol (yeast) | Harder | Slower |
Identify why it is important to control the temperature during the fermentation process to produce bioethanol.
Reveal Answer
The fermentation process requires yeast as a catalyst.
Yeast is temperature sensitive.
| Descriptor | Marks |
|---|---|
Identifies fermentation requires yeast as a catalyst | 1 |
Identifies that yeast is temperature-sensitive | 1 |
Explain why cellulose is harder to convert to glucose than starch.
Reveal Answer
Cellulose is a linear polymer. The -glucose monomers in cellulose can pack closely together. This increases hydrogen bonding between adjacent chains, which reduces interactions with water (solvents) and makes hydrolysis of cellulose more difficult than starch.
| Descriptor | Marks |
|---|---|
Identifies cellulose is a linear polymer | 1 |
Identifies monomers can pack closely together | 1 |
Explains increased H-bonding between adjacent chains makes hydrolysis of cellulose more difficult | 1 |
After 48 hours of fermentation, a 15% w/v glucose solution produces of ethanol. Calculate the percentage yield of ethanol. Show your working. (to one decimal place)
Reveal Answer
Moles
Moles
Mass g
Ethanol yield =
| Descriptor | Marks |
|---|---|
Determines 150 g glucose can produce 1.67 M of ethanol | 1 |
Calculates theoretical mass of ethanol as 76.72 g | 1 |
Calculates % yield of ethanol is 48.9% | 1 |
Which of the following is not a product of the oxidation of pentan-1-ol?
Reveal Answer
Pentanal () is a valid product formed by the partial oxidation of pentan-1-ol, which is a primary alcohol.
Carbon dioxide () is a valid product of the complete oxidation (combustion) of pentan-1-ol.
Pentan-2-one () is a ketone, which is produced by the oxidation of a secondary alcohol (like pentan-2-ol), not a primary alcohol like pentan-1-ol.
Pentanoic acid () is a valid product formed by the full oxidation of pentan-1-ol using a strong oxidizing agent.
Biodiesel and petrodiesel
have different viscosities.
have the same environmental impact.
contain molecules with no polar groups.
will flow easily through fuel lines in very cold climate conditions.
Reveal Answer
have different viscosities.
This is correct because biodiesel contains polar ester groups that create stronger intermolecular forces, resulting in a higher viscosity compared to non-polar petrodiesel.
have the same environmental impact.
This is incorrect because biodiesel is derived from renewable biomass and generally produces fewer net carbon emissions and particulates compared to fossil-fuel-derived petrodiesel.
contain molecules with no polar groups.
This is incorrect because while petrodiesel consists of non-polar hydrocarbons, biodiesel consists of fatty acid methyl esters which contain polar ester groups.
will flow easily through fuel lines in very cold climate conditions.
This is incorrect because biodiesel has a higher cloud point than petrodiesel, meaning it is more prone to gelling and restricting flow in very cold climates.
Use the following information to answer the question.
A chemist runs a mixture of hexane, hexan-1-ol and hexan-2-one through a high-performance liquid chromatography (HPLC) column using a polar mobile phase and a non-polar stationary phase.
Which of the following shows the chemicals in order of their retention times, from lowest to highest?
hexane, hexan-2-one, hexan-1-ol
hexane, hexan-1-ol, hexan-2-one
hexan-2-one, hexan-1-ol, hexane
hexan-1-ol, hexan-2-one, hexane
Reveal Answer
hexane, hexan-2-one, hexan-1-ol
This order represents the highest to lowest retention time, which would be the correct order if the stationary phase were polar (normal-phase HPLC).
hexane, hexan-1-ol, hexan-2-one
Hexane is the most non-polar compound, meaning it will interact most strongly with the non-polar stationary phase and have the highest, not lowest, retention time.
hexan-2-one, hexan-1-ol, hexane
While hexane correctly has the highest retention time, hexan-1-ol is more polar than hexan-2-one due to its ability to form hydrogen bonds, so hexan-1-ol will elute before hexan-2-one.
hexan-1-ol, hexan-2-one, hexane
In reverse-phase HPLC (non-polar stationary phase, polar mobile phase), the most polar compound has the lowest retention time. Hexan-1-ol (most polar) elutes first, followed by hexan-2-one, and the non-polar hexane elutes last.
The correct equation for the incomplete combustion of ethanol is
Reveal Answer
This equation is incorrect because combustion reactions of hydrocarbons and alcohols produce water (), not hydrogen gas ().
This equation is incorrect because it produces carbon dioxide (), which is a product of complete combustion, and hydrogen gas () instead of water.
This is correct because the incomplete combustion of ethanol produces carbon monoxide () and water (), and this chemical equation is properly balanced.
This equation represents the complete combustion of ethanol, which produces carbon dioxide () rather than the carbon monoxide () produced during incomplete combustion.
During fermentation, yeast will produce other volatile polar compounds that have similar boiling points to ethanol, .
Which one of the following methods would be most suitable to separate these compounds from ?
solvent extraction
simple distillation
fractional distillation
solvent extraction and distillation
Reveal Answer
solvent extraction
Solvent extraction relies on differences in solubility, which would likely be ineffective here since both ethanol and the other compounds are polar and may dissolve in similar solvents.
simple distillation
Simple distillation is only effective for separating liquids with significantly different boiling points (typically a difference of at least 25°C).
fractional distillation
Fractional distillation is specifically designed to separate miscible volatile liquids that have very similar boiling points.
solvent extraction and distillation
Adding solvent extraction is unnecessary and less efficient, as fractional distillation alone is the standard and most effective method for separating liquids with similar boiling points.
The question refers to the reactions below.
Reaction 1:
Reaction 2:
Identify compound Y.
CHCHCN
CHCONHCH
CHCHCHNH
HNCH(CH)COOH
Reveal Answer
CHCHCN
This is a nitrile (propanenitrile). Nitriles are typically synthesized by reacting haloalkanes with cyanide ions, not by reacting oxidation products of alcohols with amines.
CHCONHCH
Reaction 1 oxidizes ethanol to ethanoic acid () under reflux. Reaction 2 is a condensation reaction where the carboxylic acid reacts with methylamine () under heat to form an amide, N-methylethanamide.
CHCHCHNH
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.
HNCH(CH)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.
Use the following information to answer the question.
A triglyceride is reacted with methanol, , in the presence of concentrated . The products of this reaction are glycerol and Compound J.
The molecular formula of Compound J is .
What is the molecular formula of the triglyceride?
Reveal Answer
This formula is incorrect because a triglyceride must contain 6 oxygen atoms, not 3, and the carbon and hydrogen counts do not balance the transesterification reaction.
This formula is incorrect because it fails to account for the 3 carbon atoms from the glycerol backbone, resulting in 54 carbons instead of 57.
This formula is incorrect because a triglyceride contains 3 ester groups, meaning it must have 6 oxygen atoms, not 3.
This is correct. In the transesterification reaction, 1 Triglyceride + 3 Methanol () 1 Glycerol () + 3 Compound J (). Balancing the atoms yields .
Ethanol () dissolves readily in water, while decan-1-ol () has very limited solubility. Explain, with the aid of labelled diagrams, why ethanol is able to dissolve in water and decan-1-ol is not.
Reveal Answer
In order for a solute to dissolve in a solvent the energy released in the formation of the intermolecular forces between the solute and solvent are sufficient to overcome the existing intermolecular forces between the solute molecules and the solvent molecules.
Both alcohols form dispersion forces and hydrogen bonds with water.
Ethanol and water both have hydrogen bonding as their predominant type of intermolecular force.
The energy required to disrupt the hydrogen bonds in the ethanol and water are comparable to the energy released during the formation of the hydrogen bonds between the ethanol and water molecules and so dissolution occurs.
The predominant type of intermolecular force in decan-1-ol is dispersion forces.
The energy released during the formation of dispersion forces with water and decan-1-ol is not sufficient to disrupt the dispersion forces between the decan-1-ol molecules and so dissolving does not occur.
Diagrams can include:
- Diagram showing the hydrogen bonding between the ethanol and water molecules.
- Diagram showing the dispersion forces between decan-1-ol.
Response
| Descriptor | Marks |
|---|---|
A detailed, coherent response consisting of the majority of the points below (up to 6 marks): | 6 |
Diagrams
| Descriptor | Marks |
|---|---|
1 mark for each appropriate labelled diagram showing interactions between solute and solvent (up to 2 marks), for example:
| 2 |
How many moles of oxygen will be consumed in the complete combustion of 1 mole of ethanol? The unbalanced equation for this reaction is shown below.
1 mol
2 mol
3 mol
4 mol
Reveal Answer
1 mol
This is incorrect. Using 1 mole of would only provide 3 oxygen atoms on the reactant side, which is not enough to balance the carbon and hydrogen atoms in the products.
2 mol
This is incorrect. Using 2 moles of provides 5 oxygen atoms on the reactant side, which is insufficient to form the required and molecules.
3 mol
This is correct. The balanced equation is , which shows that exactly 3 moles of oxygen gas are required to completely combust 1 mole of ethanol.
4 mol
This is incorrect. Using 4 moles of would result in 9 oxygen atoms on the reactant side, which is more than the 7 oxygen atoms needed for the products.
To form ethanol biofuel in the fermentation of glucose, a catalyst is used because
less energy is required and the rate of reaction is increased.
less energy is required and the rate of reaction is decreased.
more energy is required and the rate of reaction is increased.
more energy is required and the rate of reaction is decreased.
Reveal Answer
less energy is required and the rate of reaction is increased.
Catalysts (such as the enzymes in yeast) provide an alternative reaction pathway with a lower activation energy, which allows the reaction to proceed faster.
less energy is required and the rate of reaction is decreased.
While catalysts do lower the activation energy required, they function to speed up the reaction, not slow it down.
more energy is required and the rate of reaction is increased.
Catalysts lower the activation energy required for the reaction to occur, rather than requiring more energy.
more energy is required and the rate of reaction is decreased.
This is incorrect because catalysts lower the activation energy and increase the rate of reaction.
Which would be the best reagent to use to determine whether an unknown substance was 2-methylpropan-1-ol or 2-methylpropan-2-ol?
Bromine water
Potassium nitrate solution
Sodium carbonate solution
Acidified potassium permanganate solution
Reveal Answer
Bromine water
Bromine water is used to test for the presence of carbon-carbon double bonds (unsaturation). It would not react with either of these saturated alcohols.
Potassium nitrate solution
Potassium nitrate is generally unreactive with alcohols and would not produce a visible change to help distinguish between the two substances.
Sodium carbonate solution
Sodium carbonate is typically used to test for acidic substances like carboxylic acids by observing effervescence (carbon dioxide gas), but it does not react with alcohols.
Acidified potassium permanganate solution
Acidified potassium permanganate is a strong oxidizing agent. It will oxidize the primary alcohol (2-methylpropan-1-ol), changing color from purple to colorless, but will not react with the tertiary alcohol (2-methylpropan-2-ol).