Deduce the type of chemical reaction and the reagents used to distinguish between these compounds.

State the observation expected for each reaction giving your reasons.

Deduce the number of signals and the ratio of areas under the signals in the ¹H NMR spectra of the two compounds.

Explain, with the help of equations, the mechanism of the free-radical substitution reaction of ethane with bromine in presence of sunlight.

oxidation/redox AND acidified «potassium» dichromate(VI)

OR

oxidation/redox AND «acidified potassium» manganate(VII)

Accept “acidified «potassium» dichromate” OR “«acidified potassium» permanganate”.

Accept name or formula of the reagent(s).

ALTERNATIVE 1 using K₂Cr₂O₇:

Compound A: orange to green AND secondary hydroxyl

OR

Compound A: orange to green AND hydroxyl oxidized «by chromium(VI) ions»

Compound B: no change AND tertiary hydroxyl «not oxidized by chromium(VI) ions»

Award [1] for “A: orange to green AND B: no change”.

Award [1] for “A: secondary hydroxyl AND B: tertiary hydroxyl”.

ALTERNATIVE 2 using KMnO₄:

Compound A: purple to colourless AND secondary hydroxyl

OR

Compound A: purple to colourless AND hydroxyl oxidized «by manganese(VII) ions»

Compound B: no change AND tertiary hydroxyl «not oxidized by manganese(VII) ions»

Accept “alcohol” for “hydroxyl”.

Award [1] for “A: purple to colourless AND B: no change”

Award [1] for “A: secondary hydroxyl AND B: tertiary hydroxyl”.

Accept “purple to brown” for A.

Accept ratio of areas in any order.

Do not apply ECF for ratios.

Initiation:
Br₂ 2Br•

Propagation:
Br• + C₂H₆ → C₂H₅• + HBr

C₂H₅• + Br₂ → C₂H₅Br + Br•

Termination:
Br• + Br• → Br₂

OR

C₂H₅• + Br• → C₂H₅Br

OR

C₂H₅• + C₂H₅• → C₄H₁₀

Reference to UV/hν/heat not required.

Accept representation of radical without • (eg, Br, C₂H₅) if consistent throughout mechanism.

Accept further bromination.

Award [3 max] if initiation, propagation and termination are not stated or are incorrectly labelled for equations.

Award [3 max] if methane is used instead of ethane, and/or chlorine is used instead of bromine.