Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Noradrenaline is a hormone and a neurotransmitter; it is released under stress to speed up the heart and raise blood pressure.
(a)[3]

State the names of three functional groups present in the noradrenaline molecule.

(b(i))[2]

A two-stage synthesis of noradrenaline begins with dihydroxybenzaldehyde. In the box, draw the structure of the intermediate $Z$.

(b(ii))[2]

Suggest reagents for steps 1 and 2.

(c(i))[4]

Draw the structures of the products formed when noradrenaline is reacted with dilute $\text{NaOH(aq)}$.

(c(ii))

Draw the structures of the products formed when noradrenaline is reacted with dilute $\text{HCl(aq)}$.

(c(iii))

Draw the structures of the products formed when noradrenaline is reacted with an excess of ethanoyl chloride, $\text{CH}_3\text{COCl}$.

(d)[2]

Name the functional groups newly formed in the reaction in (c)(iii).

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Any three from phenol, (secondary) alcohol, (primary) amine or arene

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