(a) From the elemental analysis the empirical formula of
Compound Q is C
5H
12O.
(b) The M
+ peak at
m/
z = 88 is evidence that the molar mass is 88 g mol
-1 and hence the molecular formula of
Compound Q is the same as its empirical formula, C
5H
12O. The fragment at
m/
z = 73 is due to loss of an methyl group, –CH
3 leaving C
4H
9O
+. The fragment at
m/
z = 45 is due loss of –C
3H
7 leaving C
2H
5O
+ with the peak at
m/
z = 43 due to C
3H
7+.
(c) From its molecular formula
Compound Q could either be an alcohol or an ether. The broad absorption at about 3300 cm
-1 is indicative of the presence of an –OH bond and hence
Compound Q is an alcohol. The peaks at approximately 3000 cm
-1 are due to C–H absorptions. The absorption at 1050 cm
-1 is likely to be due to the presence of a C−O single bond.
(d) The
1H NMR spectrum shows that the twelve hydrogen atoms are in five different chemical environments in the ratio 6:3:1:1:1. The doublet at 0.9 ppm suggests two methyl groups attached to a carbon atom containing one H atom. Similarly the doublet at 1.1 ppm suggests one methyl group attached to a carbon atom containing one H atom. The two protons with complex splitting patterns with integration traces of one indicate two separate C−H entities bonded to adjacent carbon atoms that contain more than three protons. The one at 3.6 ppm is due to the C−H proton adjacent to the carbon atom containing the −OH group. The remaining singlet at 1.8 ppm is due to the hydrogen atom of the –OH group as this will not be split.
All this information taken together confirms that
Compound Q is
3-methylbutan-2-ol, CH3CH(OH)CH(CH3)2.