Syllabus Edition
First teaching 2014
Last exams 2024
Define the term hydrocarbon.
State the general formula for the following hydrocarbon families.
Alkanes …………………………
Alkenes …………………………
State the IUPAC name of the following hydrocarbon.
A student stated that as the number of carbon atoms increases in an alkane, the boiling point increases. State if the student is correct and justify your answer.
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Propanal and propanone have the same molecular formula, C3H6O, but have different structures. Draw the displayed structures of propanal and propanone.
State the type of isomerism that is exhibited by propanal and propanone.
Butanone can be reduced to a secondary alcohol by LiAlH4. State the name of this alcohol.
State the general formula of an alcohol.
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Name the three possible isomers of C5H12.
Using IUPAC rules state the name of the molecule shown in the image below.
Draw the sterochemical drawing of methane.
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State whether the following amines can be classed either primary, secondary or tertiary.
Ethylamine ………………………….
2-aminopropane ………………………….
2-chloro-2-methylbutane is classed as a tertiary halogenoalkane.
The formulae of four organic compounds are given below. State the IUPAC names of the compounds.
State the two compounds from part (c) that will react to form an ester in the presence of concentrated sulfuric acid.
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State the formula for benzene and draw the displayed structure.
State the bond angle in the planar regular hexagon structure of benzene.
Cyclohexene is an unsaturated hydrocarbon and can undergo hydrogenation as shown below.
When benzene undergoes the same reaction with three hydrogen molecules the expected enthalpy change of the reaction is lower than expected.
State the expected value of the hydrogenation of benzene.
Explain why the enthalpy value for the hydrogenation of benzene is lower than expected.
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State the general formula for carboxylic acids.
State the IUPAC name of the following compound.
Explain why the solubility of carboxylic acids decreases as chain length increases.
Propan-2-ol will form an ester when reacted with ethanoic acid in the presence of concentrated sulfuric acid.
Draw the displayed formula for the ester formed.
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State the IUPAC names for the isomers of C5H12O that are primary alcohols.
State the IUPAC name for the following primary alcohols.
Draw the displayed formula for a straight chain isomer of CH2(Br)CH(CH3)CH2OH.
The empirical formula of the compound in part b) i).
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Draw a diagram to show the resonance structure in a molecule of benzene.
3 marksThe energy change for hydrogenation of cyclohexene is -120 kJ mol-1. However, when benzene undergoes hydrogenation, the energy change is 152 kJ mol-1 less than expected.
Use this data to explain the relative stabilities of benzene and the theoretical cyclohexa-1,3,5-triene molecule.
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Phenacetin is a pain killer though the use of this was banned as it was found to cause harm to kidney function.
Deduce the molecular formula of phenacetin.
Identify the names of the three functional groups present in phenacetin.
Aspirin is a common pain killer and has the following structure.
State the empirical formula of aspirin.
Aspirin is formed from ethanoic anhydride and compound A. State the IUPAC name of compound A.
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State the IUPAC names of two branched isomers of C5H10 that contain a π bond.
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Organic compounds are classified into families called a homologous series.
State three features of members belonging to the same homologous series.
Table 1 shows the boiling points of the first five members of the alkane family.
Table 1
|
Alkane |
Boiling point/ oC |
|
methane |
-162 |
|
ethane |
-89 |
|
propane |
-42 |
|
butane |
-1 |
|
pentane |
36 |
On the axes below in Figure 1, draw a graph of boiling point against the number of carbon atoms in the alkanes. Estimate the boiling point of the next member of the homologous series, hexane, C6H14, and show on your graph how you arrived at your estimated boiling point.
Figure 1
Estimated boiling point of hexane : ________ oC
State the general formula for an alkyne and give the molecular formula and name of the fifth member of the alkyne family.
The boiling point of ethyne, C2H2, is -84 oC.
State with, with a reason, whether the boiling point of ethyne would be expected to be higher or lower than the boiling point of ethane, C2H6.
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Geraniol is a colourless component of rose oil whose structure is shown in Figure 1.
Figure 1
Butan-2-ol is an organic compound used industrially to make butanone.
Draw and name all the branched-chain isomers of butan-2-ol.
State, with a reason, the class of alcohols which butan-2-ol belongs to.
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The formulae of four organic compounds are given in Table 1. Write the names of the compounds in the second column.
Table 1
|
compound |
name |
|
CH3CH2CH2CH(OH)CH3 |
|
|
CH3CH2COCH3 |
|
|
CH3CH2CH2OH |
|
|
CH3CH2CH2CHO |
|
Which of the compounds in part (a) are structural isomers of each other and what type of isomerism do they show?
Propofol is a drug used to reduce consciousness during medical procedures. The skeletal structure of propofol is given in Figure 1.
Figure 1
Valeric acid, C5H10O2, is a straight chain carboxylic acid found in the plant Valeriana officinalis.
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Draw and name all the possible isomers of C6H14.
Figure 1 below shows a three-dimensional structure of a molecule.
Figure 1
Explain the difference between a tertiary haloalkane and a tertiary amine, using suitable diagrams to illustrate your answer.
Three important nitrogen containing functional groups used in chemical synthesis are carboxamides, nitriles and amines.
Draw the Lewis structure of each of these functional groups.
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Benzene is an aromatic hydrocarbon which is often drawn as Figure 1.
Discuss the physical evidence that justifies this structure for benzene.
Figure 1
Benzene and cyclohexene are both unsaturated molecules, but cyclohexene reacts with bromine water and benzene does not.
State the meaning of the terms saturated and unsaturated as applied to organic molecules.
Table 1 below shows the enthalpy changes for the hydrogenation of cyclohexene, benzene, and the theoretical molecule 1,3,5-cyclohexatriene.
Table 1
|
Compound |
Enthalpy of hydrogenation |
|
Cyclohexene, C6H10 |
-120 |
|
Benzene, C6H6 |
-208 |
|
1,3,5-cyclohexatriene, C6H6 |
? |
The equations for the hydrogenation reactions are:
Cyclohexene C6H10 + H2 ⭢ C6H12
Benzene C6H6 + 3H2 ⭢ C6H12
An unknown aromatic compound has the molecular formula C8H8O2.
Deduce the structural formula of two isomers of this compound which contain an ester group.
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