Exam code: 9701
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 can react with water to form butanoic acid. State the type of mechanism that this reaction involves.
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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 2.1 to identify if compounds K, L and M from part (a) are aliphatic or aromatic.
Table 2.1
| Aliphatic | Aromatic |
compound K |
|
|
compound L |
|
|
compound M |
|
|
i) State what is meant by structural isomerism and give three specific types of structural isomerism.
[2]
ii) State what is meant by stereoisomerism and give two specific types of structural isomerism.
[2]
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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The reaction pathway for the formation of an N-substituted amide is shown in a three step synthesis in Fig. 2.1. In step 1, the major product of the reaction is formed.
Fig. 2.1
State the IUPAC names of compounds W and X.
W ...............................................
X ...............................................
Suggest suitable reagents for steps 2 and 3 given in Fig. 2.1 in part (a).
step 2 ...........................................
step 3 ...........................................
5.0 g of compound W was used to produce compound X. The percentage yield was 64%.
i) Calculate the mass, in grams, of compound X in grams and give your answer to 1 decimal place.
mass = .................... g
[3]
ii) State two reasons why the percentage yield of the reaction is not 100%.
reason 1 ....................................................................................................................................
reason 2 ....................................................................................................................................
[2]
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Table 3.1 shows the formula for different compounds.
Table 3.1
formula | name |
(CH3)2C(OH)CH(CH3)2 |
|
CH3COCl |
|
CH3CONHCH3 |
|
CH3CN |
|
Complete Table 3.1
(CH3)2C(OH)CH(CH3)2 undergoes elimination to form (CH3)2CC(CH3)2
i) Name and draw the isomer of 2,3-dimethylbut-2-ene which is also formed in the reaction.
Name ................................................................
Structure
[2]
ii) Explain why two products are obtained
[1]
When CH3COCl is heated in water, it is hydrolysed to a carboxylic acid.
i) Write the equation for the reaction that occurs
[1]
ii) Write an equation for the reaction for the formation of CH3CONHCH3 from CH3COCl
[1]
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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 |
|
i) Draw the fully displayed formula of the oxidation product of the aldehyde identified in part (a).
[1]
ii) State a suitable reagent, including observations, for the oxidation of the aldehyde identified in part (a).
[1]
i) Write a balanced symbol equation, using structural formulae, to show the reduction of the aldehyde identified in part (a). You should use [H] to show the reducing agent.
[1]
ii) State a suitable reducing agent.
[1]
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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The functionality of organic compounds, such as carbonyls, changes during a chemical reaction. These changes will depend on the reagents and conditions required for the reactions.
i) Name and draw the structure of the product of the reaction between CH3CH2CH2CHO and HCN.
name ..................................................
structure
[2]
ii) Explain the changes in shape and chirality that occur during the formation of the organic product.
[4]
In a second reaction, CH3OH reacts with CH3CH2CH2COCl.
i) Name the mechanism involved in this reaction. Describe the steps in the mechanism to support your answer.
[5]
ii) Give the systematic name of the organic product of this reaction.
[1]
An equation for the formation of phenylbutanone via the reaction of benzene with CH3CH2CH2COCl is shown in Fig. 4.1. In this reaction, a reactive intermediate is formed from CH3CH2CH2COCl which reacts with benzene.
Fig. 4.1
i) Give the formula of the reactive intermediate.
[1]
ii) Draw the three structural isomers of phenylbutanone and explain which, if any, form optical isomers.
isomer 1
| isomer 2
| isomer 3
|
[4]
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