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Chemistry HL Paper 2 (May 2024, TZ2)

  1. An organic compound, A, has the following composition by mass when its only combustion products, carbon dioxide and water, are analysed.
C / %H / %
71.9312.10

(a) Outline why this compound is not a hydrocarbon. [1]

(b) Determine the empirical formula of A. [2]

(c) A sample of the vapour of A at 200.0°C, and 1.00 × 10⁵ Pa, has a density of 2.544 × 10³ g m⁻³.
Determine the molar mass and the molecular formula of A. [2]

(d) The infrared (IR) spectrum of A is shown below.

Figure region page 5
Figure region from page 5

Identify the bond responsible for the absorption labelled B in the IR spectrum. Use section 26 of the data booklet. [1]

(e) A can be converted to compound E, which has a higher molecular mass, by heating it under reflux with acidified potassium dichromate(VI), K₂Cr₂O₇.
Identify one functional group present in E based on this information only. [1]

(f) Deduce a possible structural formula for A consistent with the evidence presented. [1]