An alcohol can be prepared by hydrolysing the halogenoalkane C2H5CHBClCH3with aqueous sodium hydroxide. The infrared spectrum for C2H5CHClCH3 is shown below with the C–Cl bond absorption labelled.
Using section 26 of the data booklet deduce how IR spectroscopy will change as a result of the above reaction.
Alcohol X has the following percentage composition by mass. Carbon = 68.2%, hydrogen = 13.6%, oxygen = 18.2%. The molecular ion peak in the mass spectrum for alcohol X occurs at m/z = 88.
i)
Use this information and section 6 of the data booklet to show that the molecular formula for alcohol X is C5H12O. Include your working.
[2]
ii)
When alcohol X is oxidised, a carboxylic acid can be formed. State what information this gives about alcohol X.
Two students, P and Q, were provided with the mass spectrum of an alkane, shown in below. Student P analysed peaks a and b and concluded that the alkane was one of two structures. Student Q analysed peaks a, b and c and was able to identify one possible alkane structure.
i)
Deduce which fragments of the alkane correspond to peaks a, b and c.
[3]
ii)
Suggest why the two students obtained different conclusions.
