This question is about two organic compounds, X and Y. Both are liquids which contain carbon, hydrogen and oxygen only.
The mass of hydrogen and of carbon present in 1.33 g of X were determined by passing its combustion products through the apparatus shown.
(2)
(2)
The experiment showed that 1.33 g of X contains 0.14 g of hydrogen and 0.63 g of carbon.
Calculate the empirical formula of X, using these data.
You must show your working.
(3)
When phosphorus(V) chloride is added to X, steamy white fumes are seen.
State what can be deduced about compound X from this observation only.
Compound X is converted into compound Y when refluxed with excess sodium dichromate(VI) in sulfuric acid.
Compound Y is a liquid that is soluble in the reaction mixture.
Draw a labelled diagram of the apparatus that could be used to separate Y from the reaction mixture.
The infrared spectrum of Y is shown.
The table shows some infrared absorption data.
Bond | Wavenumber range / cm–1 |
C—H (alkane) | 2962–2853 |
O—H (alcohols and phenols) | 3750–3200 |
O—H (carboxylic acids) | 3300–2500 |
CC (alkene) | 1669–1645 |
C O (aldehydes, ketones, carboxylic acids) | 1740–1680 |
Explain how this spectrum shows that Y contains a carboxylic acid functional group, quoting data from the table.
The mass spectrum of Y is shown.
(1)
Suggest the structure of the ion causing the peak at m / z = 43 in the mass spectrum of Y.
(1)
Compound X contains one type of functional group.
Compound Y contains two different functional groups.
Use the information in the question to deduce the structures of X and Y.
Compound X
Compound Y
Did this page help you?