Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Six compounds, P-U, are shown by their structural formulae.
(a(i))[1]

What is the empirical formula for compound T?

(a(ii))[1]

Draw the skeletal formula for compound S.

(b(i))[1]

Compounds S and U are isomers. Which type of isomerism do they exhibit?

(b(ii))[3]

Two of the six formulae P-U can each be drawn in two forms called stereoisomers. Which two compounds have formulae that can be drawn in two forms? State the type of stereoisomerism shown by each one, and identify each compound by its letter.

(c(i))[1]

Compound S can be converted into compound R. What kind of reaction is this?

(c(ii))[1]

Which reagent would you use for this reaction?

(c(iii))[1]

Write the structural formula for the compound formed when T undergoes the same reaction using an excess of the reagent you used in (c)(ii).

(d(i))[2]

Compound P may be changed into compound Q in a two-step sequence. $\text{CH}_3\text{CH}=\text{CHCH}_2\text{CH}_3 \xrightarrow{\text{step 1}} \text{intermediate} \xrightarrow{\text{step 2}} \text{CH}_3\text{CH}_2\text{COCH}_2\text{CH}_3$. What structural formula does the intermediate compound have in this sequence?

(d(ii))[1]

Outline how step 1 may be done to produce this intermediate compound.

(d(iii))[1]

What reagent would be used in step 2?

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Correct molecular formula: $\text{C}_2\text{H}_5\text{O}$

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