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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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(1)





(ii) hydroxide ions




(1)

(iii) ethanoyl chloride.




(1)



(c) 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…

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(2)





(d) 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…

Page 4

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2. (a) 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…

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(3)

(ii) 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…

Page 6

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(ii) 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.




Barnet Advisory Service 6

Page 7

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(i) 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)




Barnet Advisory Service 8

Page 9

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(iii) 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)…

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(2)




Barnet Advisory Service 10

Comments

Jack Popper

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Do you have any answers?

rgalbraith19

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Please can you upload or send me the answers?

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