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Polystyrene can be made from benzene in the series of steps shown.
1.
(a) State the type of reaction in step 1.
Identify the reagent(s) and conditions needed for step 1.
Type of reaction _____________________________________________________
Reagent(s) _________________________________________________________
Conditions _________________________________________________________
(3)
(b) State the name of the mechanism for the reaction in step 2.
Identify the inorganic reagent needed for step 2.
Name the organic product of step 2.
Name of mechanism _________________________________________________
Inorganic reagent ____________________________________________________
Name of organic product ______________________________________________
(3)
(c) The organic product of step 2 is reacted with concentrated sulfuric acid in step 3.
Outline the mechanism for step 3.
(3)
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(d) Draw the repeating unit of polystyrene.
(1)
(Total 10 marks)
Paracetamol is a medicine commonly used to relieve mild pain.
2.
Traditionally, paracetamol has been made industrially in a three-step synthesis from phenol.
(a) Name the mechanism of the reaction in Step 1.
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(1)
(b) Complete the equation for the reaction in Step 2.
(1)
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(c) In theory, either ethanoyl chloride or ethanoic anhydride could be used in Step 3.
Complete the mechanism for the reaction of 4-aminophenol with ethanoyl chloride.
RNH2 is used to represent 4-aminophenol in this mechanism.
(2)
(d) In practice, ethanoic anhydride is used in the industrial synthesis rather than ethanoyl
chloride.
Give one reason why ethanoyl chloride is not used in the industrial synthesis.
___________________________________________________________________
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(1)
(e) In Step 3 other aromatic products are formed as well as paracetamol.
Draw the structure of one of these other aromatic products.
(1)
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(f) Chemists have recently developed a two-step process to produce paracetamol from
phenol.
In the first step, phenol is oxidised to hydroquinone.
In the second step, hydroquinone reacts with ammonium ethanoate to form paracetamol.
Complete the equation for this second step.
(1)
(g) Calculate the mass, in kg, of hydroquinone (Mr = 110.0) needed to produce 250 kg of
paracetamol.
Mass _________________________ kg
(3)
(Total 10 marks)
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When methylbenzene reacts with ethanoyl chloride in the presence of aluminium chloride, the
3. product, H, is formed.
(a) Deduce the molecular formula of H.
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(1)
(b) Two other isomers are also produced in the reaction.
Draw the structure of one of the other isomers.
Name the type of structural isomerism shown by these three products.
Structure
Type of isomerism __________________________________________________
(2)
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(c) Name and outline the mechanism for the reaction of ethanoyl chloride with methylbenzene
to produce H.
Include an equation for the formation of the reactive intermediate that is involved in the
reaction.
Name _____________________________________________________________
Equation ___________________________________________________________
Mechanism
(5)
(Total 8 marks)
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Compound X (ClCH2COCl) is used as a reagent in organic synthesis.
4.
(a) One important reaction of X is in the preparation of compound P as shown.
(i) Draw the structure of the electrophile formed by the reaction of X with AlCl3.
(1)
(ii) Outline the mechanism for the reaction of the electrophile from part (a)(i) with
benzene in the preparation of P.
(3)
(b) Compound Q is an alternative product that could be formed when X reacts with benzene.
Describe how you could distinguish between P and Q by a test-tube reaction.
Give the reagent used and the observation with each compound.
Reagent _________________________________________________________
Observation with P _________________________________________________
Observation with Q _________________________________________________
(3)
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(c) X is also used to make the compound HOCH2COOH. This compound is polymerised to
form the polymer known as PGA. PGA is used in surgical sutures (stitches).
(i) Draw the repeating unit of PGA.
(1)
(ii) Production of PGA occurs via a cyclic compound. Two HOCH2COOH molecules react
together to form the cyclic compound and two molecules of water.
Draw the structure of this cyclic compound.
(1)
(d) Poly(propene) is also used in surgical sutures.
(i) Draw the repeating unit of poly(propene).
(1)
(ii) Suggest an advantage of surgical sutures made from PGA rather than from
poly(propene).
Explain your answer.
______________________________________________________________
______________________________________________________________
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(2)
(Total 12 marks)
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Consider the following reaction sequence starting from methylbenzene.
5.
(a) Name the type of mechanism for reaction 1.
___________________________________________________________________
(1)
(b) Compound J is formed by reduction in reaction 2.
(i) Give a reducing agent for this reaction.
______________________________________________________________
(1)
(ii) Write an equation for this reaction. Use [H] to represent the reducing agent.
______________________________________________________________
(1)
(iii) Give a use for J.
______________________________________________________________
(1)
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(c) Outline a mechanism for the reaction of bromomethane with an excess of compound J.
You should represent J as RNH2 in the mechanism.
(4)
(d) Compound K (C6H5CH2NH2) is a structural isomer of J.
Explain why J is a weaker base than K.
___________________________________________________________________
___________________________________________________________________
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___________________________________________________________________
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(3)
(Total 11 marks)
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The following reaction scheme shows the formation of two amines, K and L, from
6. methylbenzene.
(a) (i) Give the reagents needed to carry out Step 1. Write an equation for the formation
from these reagents of the inorganic species which reacts with methylbenzene.
Reagents ______________________________________________________
Equation ______________________________________________________
(ii) Name and outline a mechanism for the reaction between this inorganic species
and methylbenzene.
Name of mechanism _____________________________________________
Mechanism
(7)
(b) Give a suitable reagent or combination of reagents for Step 2.
___________________________________________________________________
(1)
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(c) (i) Give the reagent for Step 4 and state a condition to ensure that the primary amine is
the major product.
Reagent _______________________________________________________
Condition ______________________________________________________
(ii) Name and outline a mechanism for Step 4.
Name of mechanism _____________________________________________
Mechanism
(7)
(Total 15 marks)
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