JEE Advanced levelSingle correct optionDifficulty 3 of 3si097
A compound shows molecular ion peaks at m/z 186, 188 and 190 in the ratio about 1:2:1 (lowest mass peak is from 79Br only). It contains only C, H and Br, is saturated and acyclic, and gives a single signal in its 1H NMR spectrum. The compound is
A1,1-dibromoethane
B1,2-dibromoethane
C1,2-dibromopropane
D1,1,2-tribromoethane
Answer: B
The 1:2:1 cluster shows two Br atoms. 186−2×79=28, which is CX2HX4, so the formula is CX2HX4BrX2 (degree of unsaturation 0). BrCHX2CHX2Br has four equivalent hydrogens (one signal), whereas CHX3CHBrX2 has two signals.