CAIE A-Level Chemistry AS Reference Structural Displayed and Skeletal Formula Conventions Questions

Practise representing organic compounds with structural, displayed and skeletal formulae, including clear partial structures and the preferred aromatic ring convention.

Exam points

draw unambiguous structural and displayed formulae for named organic compounds
convert between structural and skeletal representations, including partial-skeletal forms
use the preferred aromatic ring convention when drawing organic structures

[Maximum number: 2]

C, D and E are isomers of each other.
They are made by passing an alcohol vapour over an aluminium oxide catalyst.

F is an organic molecule which has the molecular formula $\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}_{2}$ . When F is heated with NaOH(aq) followed by $\mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})$ the products G and H are made.

\underset{\mathrm{C}_{3} \mathrm{H}_{6} \mathrm{O}_{2}}{\mathbf{F}} \xrightarrow[\text { by } \mathrm{H}_{2} \mathrm{SO}_{4}(\mathrm{aq})]{\mathrm{NaOH}(\mathrm{aq}) \text { followed }}+\mathbf{G}^{\mathbf{F}}+\mathbf{H}_{\mathbf{S}}^{\mathbf{F}}

Separate samples of G and H are added to
- $\mathrm{Na}_{2} \mathrm{CO}_{3}(\mathrm{aq})$
- sodium metal
- alkaline aqueous iodine.

The observations are described in the table.

Table for Question CAIE A-Level Chemistry AS Reference Structural Displayed and Skeletal Formula Conventions Questions question 1 — CAIE A-Level Chemistry AS

Draw the structures of G and H.

Figure for Question CAIE A-Level Chemistry AS Reference Structural Displayed and Skeletal Formula Conventions Questions question 1 — CAIE A-Level Chemistry AS

Correct structures:
$\mathbf{M1}\quad G = \mathrm{HCOOH} / \mathrm{HCO}_2\mathrm{H}$ $\mathbf{M2}\quad H = \mathrm{C}_2\mathrm{H}_5\mathrm{OH}$

G = \mathrm{HCOOH};\quad H = \mathrm{C}_2\mathrm{H}_5\mathrm{OH}

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CAIE A-Level Chemistry AS Reference Structural Displayed and Skeletal Formula Conventions Questions question 1