Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 12, Problem 12.21P
Interpretation Introduction

(a)

Interpretation:

The α cleavage process of CH3OCH2CH(CH3)2 is to be predicted. The structure of the ion with mass =45 is to be drawn.

Concept introduction:

Spectroscopy method is used to identify the structure of the substance. The mass spectroscopy is used to determine the molecular mass. In the mass spectrum, the molecular ion is the most important peak. The m/z of the molecular ion occurs at the molecular mass.

Interpretation Introduction

(b)

Interpretation:

The reason as to why the mass spectrum of methyl isobutyl ether does not show a peak due to inductive cleavage, in contrast to the mass spectrum of di-sec-butyl-ether is to be stated.

Concept introduction:

Spectroscopy method is used to identify the structure of the substance. The mass spectroscopy is used to determine the molecular mass. In the mass spectrum, the molecular ion is the most important peak. The m/z of the molecular ion occurs at the molecular mass.

Interpretation Introduction

(c)

Interpretation:

The major difference that is expected when comparing the CI mass spectrum of methyl isobutyl ether with its EI spectrum is to be stated.

Concept introduction:

The mass spectroscopy is used to determine the molecular mass. In the mass spectrum, the molecular ion is the most important peak. The m/z of the molecular ion occurs at the molecular mass.

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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-propanol shows a large peak at m/z=31. Draw the structure of the fragment and explain why it is particularly stable.
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