A-LevelChemistryIntroduction to organic chemistry9701/43 · May/June 2018 · Q95 Marks

Noradrenaline is a hormone found in humans. [Figure showing structure of noradrenaline]

(a)Give the molecular formula of noradrenaline.[1]
(b)State whether or not noradrenaline shows stereoisomerism. Explain your answer.[1]
(c)(i)Suggest why the diazonium ion produced with phenylamine is stable.[1]
(c)(ii)When one noradrenaline molecule reacts with one HNO2 molecule, the products are one water molecule, one molecule of an unreactive gas, and one molecule of an organic compound made up of carbon, hydrogen and oxygen only. Complete the chemical equation for this reaction. [Figure showing noradrenaline + HNO2 → products][2]

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Mark scheme

Marking points from the official mark scheme (May/June 2018). The mark or mark type is shown in brackets.

[1] C8H11O3N
[1] yes, as it has a chiral C atom
[1] (phenyldiazonium ion is stabilised because) positive charge is delocalised by ring / positive charge is spread over ring
[1] (structure for the organic product - with -NH2 replaced by -OH)
[1] N2

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