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Date May 2013 Marks available 1 Reference code 13M.2.sl.TZ1.5
Level SL Paper 2 Time zone TZ1
Command term Apply Question number 5 Adapted from N/A

Question

The following diagram shows the three-dimensional structure of a molecule.

M13/4/CHEMI/SP2/ENG/TZ1/05

Apply IUPAC rules to state the name of this molecule.

[1]
a.

Deduce the structural formula of two isomers of the molecule above with the same functional group.

[2]
b.

Describe, using an equation, the oxidation by acidified potassium dichromate(VI) of the substance shown in the diagram. Use the symbol [O] to represent the oxidizing agent.

[1]
c.

Markscheme

butan-2-ol/2-butanol;

a.

CH3CH2CH2CH2OH;

(CH3)2CHCH2OH;

(CH3)3COH;

Accept condensed or full structural formulas.

Penalise missing H atoms or incorrect bonds (such as C–HO, C–H2C) only once in the whole paper.

b.

C2H5CHOHCH3+[O]C2H5COCH3+H2O;

Accept condensed or full structural formulas.

Accept [O] on top of the arrow.

Do not accept equation without H2O.

Do not accept equation with H+/Cr2O72–.

c.

Examiners report

Most candidates gave the correct name, though often but-2-anol was given.

a.

The question was fairly well answered, though a common error was drawing butan-2-ol in different layouts.

b.

Almost universally unsuccessful. Most students did not follow the instructions and did not use [O] for the oxidizing agent, and the few who did, did not give water as the other product.

c.

Syllabus sections

Core » Topic 10: Organic chemistry » 10.1 Fundamentals of organic chemistry
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