(a) From the elemental analysis the empirical formula of
Compound R is C
2H
4Cl.
(b) The M
+ peak at
m/
z = 126 is evidence that the molar mass is 126 g mol
-1 and hence the molecular formula of
Compound R is twice its empirical formula, i.e. C
4H
8Cl
2. 126 g mol
-1 is the molar mass when the isotopes of the two chlorine atoms are both
35Cl. The peak at
m/
z = 128, the (M+2)
+ peak, is when one of the Cl atoms is
35Cl and the other
37Cl. The peak at
m/
z = 140, the (M+4)
+ peak, is when both of the chlorine atoms are
37Cl. The fragment at
m/
z = 63 is due to the molecule being split in half to give C
2H
435Cl
+. The smaller peak at at
m/
z = 65 is due to C
2H
437Cl
+. The fragment at
m/
z = 62 is due to loss of a further proton to give C
2H
335Cl
+ with a smaller peak for the analogous fragment containing the other isotope of chlorine, C
2H
337Cl
+ at
m/
z = 64. From its molecular formula
and its fragmentation pattern
Compound R looks to be a symmetrical dichloroalkane.
(c) The absorptions at approximately 3000 cm
-1 are due to C–H and the absorption at 650 cm
-1 is likely to be due to the presence of a C−Cl single bond.
(d) The
1H NMR spectrum shows that the eight hydrogen atoms are in two different chemical environments in the ratio 3:1. The doublet centred at at 1.6 ppm suggests two separate methyl groups each attached to a carbon atom containing one H atom. Similarly the complex doublet centred at 4.1 ppm suggests two C-H entities each attached to a –CH
3 group and to a –C−H entity
All this information taken together confirms that
Compound R is 2,3-dichlorolbutane, CH
3CHClCHClCH
3.