Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Compound F has been discovered in small amounts in certain cereals and dried fruits.
(a(i))[2]

State the names of the functional groups marked A and B.

(a(ii))[1]

State how many chiral carbon atoms are present in one molecule of F.

(b)[3]

F may be hydrolysed by heating it with an excess of dilute hydrochloric acid, as shown. Three products are produced: G and two others. Draw the structures of the other products from the reaction in the boxes provided.

(c(i))[1]

Compound H is produced in one step in a different synthesis, as shown. State the role of $\text{FeCl}_3$ in this step.

(c(ii))[2]

Use the Data Booklet to suggest two reasons why the chlorine atom in compound H enters the ring at the position shown, rather than at the other positions in the ring. 1 .................................................. 2 ..................................................

(d(i))[2]

Compound J, $\text{C}_x\text{H}_y\text{O}_z$, is also found in some cereals. A section of the mass spectrum of J is shown. The M and M+1 peaks are labelled, together with their relative intensities. Calculate the number of carbon atoms, $x$, present in J.

(d(ii))[1]

There is a peak at $m/e = 205$ in the mass spectrum. Suggest the identity of the fragment that is lost from J to form this peak.

Worked solution & mark scheme

This 12-mark question has a full step-by-step worked solution and mark scheme. One marking point: A is an ester, whereas B is a secondary amide

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