Aromatic chemistry practice questions

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Aromatic Chemistry
1. (a) Silk contains the amino acid, serine.
(i) Draw the structure of the species present in solid serine which causes it to be a
solid at room temperature.
(1)
(ii) Explain why this structure causes serine to have a high melting temperature.
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(2)
(b) Draw the structural formula of the organic product formed when serine reacts with:
(i) hydrogen ions
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Terylene, a polyester, can be made from the dicarboxylic acid, HOOC­C6H4­COOH,
and ethane1,2diol.
(i) Draw the structural formula of ethane1,2diol.
(1)
(ii) Draw the repeat unit of the polyester formed from these monomers, showing all the
bonds in the ester link.…read more

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Methanol is produced when the ester, methyl ethanoate, reacts with sodium hydroxide
solution.
CH3COOCH3 + NaOH CH3COONa + CH3OH
It is also produced when methyl ethanoate reacts with an acid such as hydrochloric acid.
(i) Classify the type of reaction taking place between methyl ethanoate and sodium
hydroxide solution.
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(1)
(ii) Explain why it is better to make methanol by reacting methyl ethanoate with sodium
hydroxide solution, rather than with hydrochloric acid.
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Give the structural formula of the organic product when phenol is reacted with:
(i) sodium hydroxide solution
(1)
(ii) aqueous bromine
(1)
(iii) ethanoyl chloride.
(1)
(b) An azo dye can be made from benzenediazonium chloride.
(i) State the reagents and conditions needed to make benzenediazonium chloride from
phenylamine.
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Write an equation, using structural formulae, to show the reaction between
benzenediazonium ions and phenol to give the azo dye.
(2)
(iii) What condition is required for the reaction in (ii) above?
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(1)
(Total 9 marks)
3. (a) Benzene reacts with 2bromopropane in a FriedelCrafts reaction to give
2phenylpropane, C6H5CH(CH3)2, usually known as cumene.
Cumene is used to manufacture phenol and propanone.
(i) Identify a suitable catalyst for the reaction between benzene and 2bromopropane.
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Give the mechanism for the reaction, including the formation of the electrophile.
(4)
(b) If benzene and 1bromopropane, CH3CH2CH2Br, are reacted under similar conditions to
those in part (a), the product is still cumene although 1phenylpropane C6H5CH2CH2CH3
might have been the expected product.…read more

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Draw the structure of the carbocation which would initially be formed.
(1)
(ii) Suggest, in terms of relative stabilities of carbocations, what happens to the
carbocation in (i) which results in cumene as the product of the reaction rather than
1phenylpropane.
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(2)
(c) Phenol reacts with the benzenediazonium cation, C6H5N2+, in alkaline conditions to give
an azo dye.
(i) State the reagents needed to convert phenylamine into a solution containing
C6H5N2+ ions.
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Give the structural formula of the product from the reaction between
benzenediazonium chloride and phenol.
(2)
(d) (i) How would you show that propanone is a carbonyl compound and is a ketone,
not an aldehyde?
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(3)
(ii) A characteristic reaction of the carbonyl group, C O, is nucleophilic addition.
The C C double bond reacts by electrophilic addition.
Suggest the reason for the difference.
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