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Chapter 12: Q.9P (page 629)

Show the fragmentations that give rise to the peaks at m/z 43, 57, and 85 in the mass spectrum of 2,4-dimethylpentane (Figure 12-17).

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01

2,4-dimethylpentane

The given compound 2,4-dimethylpentane has has three types of carbons in it. They are primary, secondary, and tertiary. Its structure is shown below.

Structure of the given compound

02

Peat at m/z 43

Solution: fragmentations of 2,4-dimethylpentane

molecular mass(m/z) of 2,4-dimethylpentane is 100.

Formation of m/z 43 ion:

Peak at m/z 43

03

Peat at m/z 57

Formation of m/z 57 ion

Peak at m/z 57

04

Peat at m/z 85

Formation of M/z 85 ion

Peak at m/z 85

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Most popular questions from this chapter

Question: A C-D (carbon鈥揹euterium) bond is electronically much like a C-H bond, and it has a similar stiffness, measured by the spring constant, k. The deuterium atom has twice the mass (m) of a hydrogen atom, however.

(a) The infrared absorption frequency is approximately proportional tokm , when one of the bonded atoms is much heavier than the other, and m is the lighter of the two atoms (H or D in this case). Use this relationship to calculate the IR absorption frequency of a typical C-D bond. Use as a typical C-H absorption frequency.

(b) A chemist dissolves a sample in deuterochloroform (CDCl3) and then decides to take the IR spectrum and simply evaporates most of theCDCl3 . What functional group will appear to be present in this IR spectrum as a result of theCDCl3 impurity?

Three IR spectra are shown, corresponding to three of the following compounds. For each spectrum, determine the structure and explain how the peaks in the spectrum correspond to the structure you have chosen.

Chapter-9 covered a synthesis of alkynes by a double dehydrohalogenation of dihalides. A student tried to convert trans-2,5-dimethylhex-3-yne by adding bromine across the double bond and then doing a double elimination. The infrared and mass spectra of the major product are shown here.

  1. Do the spectra confirm the right product? If not, what is it?
  2. Explain the important peaks in the IR spectrum.

Question: Consider the following four structures, followed by mass spectral data. Match each structure with its characteristic molecular ion or fragment. In each case, give a likely structure of the ion responsible for the base peak

(a) base peak at 105

(b) base peak at 72

(c) doublet at 198 and 200, base peak at 91

(d) base peak at 91, large peak at 43


Question:Spectra are given for three compounds. Each compound has one or more of the following functional groups: alcohol, amine, ketone, aldehyde, and carboxylic acid. Determine the functional group(s) in each compound, and assign the major peaks above 1600cm-1.
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