The structural formulae of four different organic compounds are shown in Table 1.1.
Table 1.1
| Structural formula | IUPAC name |
| C6H5CH3 | |
| CH3CH2CH2CH2CHO | |
| CH3NHCH3 | |
| CH3CH(NH2)CO2H |
Complete Table 1.1 by writing the systematic name for each compound.
Draw the fully displayed formula for butanoyl chloride.
butanoyl chloride |
Butanoyl chloride can react with water to form butanoic acid. State the type of mechanism that this reaction involves.
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This question is about benzene.
Draw the displayed formula for benzene.
State the bond angle in the planar regular hexagon structure of benzene.
State the type of hybridisation of the carbon atoms in benzene.
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This question is about isomerism in different acids.
Hydroxypropanoic acid has two position isomers.
There are 20 amino acids used, by the cells in the human body, for protein synthesis. There is only one amino acid that is not optically active.
Three amino acids are shown in Fig. 3.1.
Fig. 3.1
Identify the amino acid that does not have any effect on plane polarised light.
Serine, shown in Fig. 3.2, exhibits optical activity.
Fig. 3.2
Draw three-dimensional representations of the two isomers to show the relationship between them.
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Benzene can react with aluminium bromide, AlBr3, and bromoethane, CH3CH2Br, to form ethylbenzene.
Write the equation for the formation of the CH3CH2+ species.
Name the mechanism for the formation of ethylbenzene from benzene and aluminium bromide.
Using the CH3CH2+ electrophile, draw the mechanism for the conversion of benzene into ethylbenzene. Include all necessary curly arrows and charges.
State the type of reaction that occurs in part (c).
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Compounds K, L and M are organic compounds with different properties.
| K | L | M |
 |
 |
 |
Give the systematic name of compounds K, L and M.
compound K ................................................................................
compound L ................................................................................
compound M ................................................................................
Complete Table 5.1 to identify if compounds K, L and M from part (a) are aliphatic or aromatic.
Table 5.1
| Aliphatic | Aromatic | |
| compound K | ||
| compound L | ||
| compound M |
Draw three-dimensional diagrams to show the stereoisomers of compound M.
|
isomer 1
|
isomer 2
|
 |
 |
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Organic compounds can be represented using skeletal formula.
Give the IUPAC names of the compounds A, B and C.
Compound A can undergo hydrolysis to form a carboxylic acid.
Explain why this is an example of an addition-elimination reaction.
When heated, compound A will also react with phenol in the presence of a base to produce phenyl butanoate.
Draw the displayed formula of phenyl butanoate.
State whether any of the compounds, A, B or C, can form optical isomers.
Explain your answer.
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Benzene can exist as C6H6 or be substituted in a number of different ways to form aromatic compounds.
State the IUPAC name for compounds W, X and Y.
State the IUPAC name for compound Z.
State the bond angle that is present in the benzene molecule.
In benzene, each of the carbon atoms is sp2 hybridised.
[1]
[1]
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This question is about benzene.
[2]
[1]
Benzene can be nitrated by warming it with a mixture of concentrated sulfuric acid and concentrated nitric acid.
The mechanism for the reaction is shown in Fig. 3.1.
Name the type of mechanism of this nitration reaction. Explain your answer.
Benzene can be used to synthesise (4-aminophenyl)ethanoic acid which is a drug that can be used to treat chronic inflammation of the intestines.
[1]
Fig. 3.2
[1]
Noradrenaline, shown in Fig. 3.3, is a hormone and neurotransmitter which contains a benzene ring. It is released during stress to stimulate the heart and increase blood pressure.
Fig. 3.3
Other than the arene functional group, state the name of three functional groups in the noradrenaline molecule.
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Leucine is an optically active amino acid with the molecular formula (CH3)2CHCH2CH(NH2)COOH.
Draw the displayed formula of leucine.
Leucine exists as stereoisomers.
Explain the meaning of the term stereoisomers.
[2]
The two optical isomers of leucine taste different. One isomer has a bitter taste, the other is sweet.
Draw the three-dimensional arrangement of the two optical isomers.
Give the IUPAC name of leucine.
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Propranolol is an optically active drug that is used to treat hypertension. Its structure is shown in Fig. 5.1.
Fig. 5.1
[1]
[1]
Explain why a racemic mixture of propranolol has no effect on plane polarised light.
Explain why it is important to separate a racemic mixture of propranolol into pure single enantiomers.
Chiral catalysts are often used in the manufacturing process of drugs.
[1]
[2]
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This question is about aldehydes.
Draw the displayed formula and 3D representations of the smallest aldehyde that can form optical isomers.
| displayed formula |
|
|
| optical isomer 1 | optical isomer 2 |
Name the organic compound formed by the reaction of the oxidation product in part (b) and the reduction product in part (c).
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This question is about the chemistry of limonene.
Limonene is commonly found in the rinds of citrus fruits such as grapefruit, lemon, lime and oranges. It is a naturally occurring hydrocarbon with the molecular formula C10H16.
Limonene exists as a pair of enantiomers:
Draw 3D representations of the two enantiomers of limonene.
| optical isomer 1 | optical isomer 2 |
Suggest why receptors in the human nose can distinguish between the orange and lemon enantiomers of limonene.
4 marksLimonene can undergo full hydrogenation to form menthane as shown.
For the complete hydrogenation of an impure sample of 3.00 g of limonene at room temperature and pressure, 870 cm3 of hydrogen was required.
Calculate the percentage purity of limonene.
(1 mol of hydrogen occupies 24.0 dm3 at room temperature and pressure)
percentage purity = ........................ %
The final step of the multi-step synthetic conversion of limonene to menthol is shown.
State the reagent for this reaction and the type of reaction.
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Aldehydes and ketones always react with HCN to form optical isomers.
Discuss this statement, using the general formulae RCHO and R’COR’’. Your answer should include equations where appropriate.
Acidified K2CrO7 (aq) was heated under reflux with the following β-hydroxyaldehyde shown in Fig. 3.1.
Explain the change in chirality, if any, between the β-hydroxyaldehyde and its organic product.
Other isomers of pent-1-en-3-ol, C5H10O, exist.
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