Chapter 14, Problem 43P

In the mass spectrum of the following compounds, which is the tallest—the peak at m/z =57 or the peak at m/z = 71?

1. a. 3·methylpentane
2. b. 2·methylpentnne

Interpretation Introduction

Interpretation

The tallest peak should be identified.

Explanation of Solution

Mass fragmentation of 3-methyl pentane: In this molecule will be more adopted to lose an ethyl radical forming a secondary carbocation and a primary radical than a methyl radical forming secondary carbocation and methyl radical.  In addition, 3-methylpentane ha undergoes for two path ways to lose an ethyl radical,

Therefore, the peak at would be intense than the peak at , the corresponding fragmentations has shown below.

Mass fragmentation of 2-methyl pentane: The 2-methylpentane has undergoes for pathways to lose a methyl radical in each pathway and it cannot form a secondary carbocation by losing an ethyl radical.  Loss of an ethyl radical would form a primary carbocation and a primary radical. Therefore, it will be more adopt to lose a methyl radical than an ethyl radical, the corresponding peak at would be more intense than the peak at

Conclusion

The 3-methyl pentane molecular peak at the m/e=71 has more intense then the peak at