State the IUPAC names of each of the compounds, D, E, F and G.

D:

E:

F:

G:

State the reagents and reaction conditions used to convert D to E and D to F directly.

Discuss the volatility of E compared to F.

D: 4-methylpentan-1-ol;

Allow 4-methyl-1-pentanol.

E: 4-methylpentanal;

F: 4-methylpentanoic acid;

G: 4-methylpentyl ethanoate;

Allow 4-methylpentyl acetate.

Award [2] for all four correct, [1 max] for two or three correct.

Award [1 max] if all suffices correct but prefix (4-methyl or pent) not correct.

For both reactions reagents:

named suitable acidified oxidizing agent;

Suitable oxidizing agents are potassium dichromate(VI)/K₂Cr₂O₇ / sodium dichromate(VI)/Na₂Cr₂O₇ / dichromate/Cr₂O₇^2– / potassium manganate(VII)/potassium permanganate/KMnO₄ / permanganate/manganate(VII)/MnO₄^–.

Accept H⁺/H₂SO₄ instead of sulfuric acid and acidified.

Allow potassium dichromate or sodium dichromate (i.e. without (VI)) or potassium manganate (i.e. without (VII).

Conditions:

distillation for D to E and reflux for D to F;

Award [1 max] if correct reagents and conditions identified for one process only.

Volatility:

E more volatile than F;

hydrogen bonding in carboxylic acid/F;

Accept converse argument.

Many candidates only scored one mark.

Distillation often was not mentioned.

(iv) was very well answered.