Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

The diagram sets out a reaction pathway that begins with ethanal.
(a(i))[1]

Draw the displayed formula for P.

(a(ii))[1]

State the type of chemical reaction taking place in reaction 3.

(a(iii))[1]

Write an equation for reaction 4. Use [O] to stand for the oxidising agent.

(a(iv))[1]

State the reagents and conditions needed for reaction 4.

(b(i))[1]

Explain the meaning of the term optical isomers.

(b(ii))[2]

Draw the two optical isomers of $\text{Q}$, showing their three-dimensional structures clearly.

(c)[3]

$\text{R}$ can be used in a two-step route to make polymer $\text{W}$. Draw one repeat unit of $\text{W}$.

(d(i))[2]

In the first stage, $\text{Z}$ reacts with HBr to give two products. Which product forms depends on whether intermediate I or intermediate II is made. Explain why intermediate I is more likely to form than intermediate II.

(d(ii))[3]

When intermediate I is formed, the first-step product is $\text{T}$. Complete the diagram to show the mechanism for converting $\text{Z}$ into $\text{T}$. Include all relevant charges, partial charges, curly arrows and lone pairs.

(d(iii))[1]

$\text{T}$ can then be turned into 2-aminopropane. Name the mechanism for this change.

(e(i))[2]

Compound $\text{S}$, $\text{CH}_3\text{COCO}_2\text{H}$, may be reduced by LiAlH$_4$. Complete the equation using structural formulae for this reaction. Use $[\text{H}]$ to represent the reducing agent.

(e(ii))[1]

Give the electronic configuration of the $\text{Na}^+$ cation.

(e(iii))[1]

Suggest why ionic radius increases down Group 1.

Worked solution & mark scheme

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