EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
6th Edition
ISBN: 8220103151757
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 20, Problem 20.56AP
Interpretation Introduction

(a)

Interpretation:

The fragmentation mechanisms for the observation of strong peak at m/z=74 in EI mass spectrum of 2-methylpentanoicacid is to be stated.

Concept introduction:

The EI mass spectrum is one of the types of mass spectrum in which an organic compound is vaporized and is analyzed by the bombardment with high energy electrons. When high energy passes by the molecule, it ejects an electron. The molecule results in the formation of the radical cation. This radical cation is then fragmented into small pieces. The rate of fragmentation depends upon the stability of the radical cation.

Interpretation Introduction

(b)

Interpretation:

The fragmentation mechanisms for the observation of strong peak at m/z=105 and

m/z=77 in EI mass spectrum of benzoic acid is to be stated.

Concept introduction:

The EI mass spectrum is one of the types of mass spectrum in which an organic compound is vaporized and is analyzed by the bombardment with high energy electrons. When high energy passes by the molecule it ejects an electron the molecules results in the formation of the radical cation. This radical cation is then fragmented into small pieces and rate of fragmentation depends upon the stability of the radical cation.

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1 (c) 2-Methyl-3-pentanol reacts with PCC to form compound F. (i) Draw the structure of F. (ii) In the mass spectrum, identify the m/z value of the molecular ion peak for compound F. (ii) Fragmentation of radical cation F exhibits two fragment ion peaks at m/z 57 and m/z 71. Propose the structures of these two fragments. (iv) Draw the resonance structure for each of the cation in (iii).
2,3-Dimethylbutane and 2,2-dimethylbutane have the same molecular ion in the mass spectrum, but only one of these isomers gives a significant fragment at m/z = 57. (a) Which isomer shows an intense peak at m/z = 57? (b) Propose a structure for the ion that gives rise to this peak. (c) The base peak in the mass spectrum of the other isomer occurs at m/z = 43. What ion gives rise to this peak?
The mass spectrum of 1-ethyl-1-methylcyclohexane shows many fragments, with two in very large abundance. Kne appears af m/z=111 and the other appears at m/z=97. Identify the structure of each of these fragments.
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