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Carbonyl compounds

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Question 2

This question is about carbonyl compounds.

a.

Describe a chemical test to confirm the presence of a carbonyl group. How could the product of this test be used to identify the specific carbonyl compound? Your answer should not include spectroscopy.

[3]
b.

Describe a chemical test that would identify whether a carbonyl compound is an aldehyde. Your answer should include the reagent and observations.

[2]
c.

A student is provided with two unknown carbonyl compounds, F and G.

The compounds are analysed and found to have identical percentage compositions by mass: C:66.67%\text{C}: 66.67\%C:66.67%; H:11.11%\text{H}: 11.11\%H:11.11%; O:22.22%\text{O}: 22.22\%O:22.22%

The mass spectra of the two compounds show the following key features:

  • Compound F has a molecular ion peak at m/z=72m/z = 72m/z=72 and a significant fragment peak at m/z=29m/z = 29m/z=29.
  • Compound G has a molecular ion peak at m/z=72m/z = 72m/z=72 and a significant fragment peak at m/z=43m/z = 43m/z=43.

Use this information to identify the structures of the two compounds. Include relevant fragment ions present in the mass spectrum of each compound and draw their structures.

[6]
d.

The organic compound H contains carbon, hydrogen, and oxygen only and has an MrM_rMr​ of 114.0114.0114.0. Compound H has two carbonyl groups and no other functional groups.

The 1H^1\text{H}1H NMR spectrum of organic compound H shows:

  • A multiplet (quartet) centred at δ=3.8 ppm\delta = 3.8\text{ ppm}δ=3.8 ppm (relative peak area = 1)
  • A singlet at δ=2.1 ppm\delta = 2.1\text{ ppm}δ=2.1 ppm (relative peak area = 6)
  • A doublet at δ=1.4 ppm\delta = 1.4\text{ ppm}δ=1.4 ppm (relative peak area = 3)

Analyse the spectrum to suggest a possible structure for compound H. Show all your reasoning.

[5]

Carbonyl compounds Questions

  1. A Level
  2. /Chemistry
  3. /Carbonyl compounds