EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 12, Problem 27P

(a)

Interpretation Introduction

Interpretation:

The alkane with molecular formula, C5H12 that forms only one monochlorinated product when heated with Cl2 has to be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Chlorination:

EBK ORGANIC CHEMISTRY, Chapter 12, Problem 27P , additional homework tip  1

2-methyl propane undergoes radical chlorination which yields the 2-bromo-2-methylpropane and 1-bromo-2-methyl propane.

(b)

Interpretation Introduction

Interpretation:

The alkane with molecular formula, C7H16 that forms seven monochlorinated products when heated with Cl2 has to be given.

Concept introduction:

Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.

Bond strength is depends on the formation of the radical, if the radical is involving in resonance which is weakest bond strength.

Chlorination:

EBK ORGANIC CHEMISTRY, Chapter 12, Problem 27P , additional homework tip  2

2-methyl propane undergoes radical chlorination which yields the 2-bromo-2-methylpropane and 1-bromo-2-methyl propane.

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Relative Intensity Part VI. consider the multi-step reaction below for compounds A, B, and C. These compounds were subjected to mass spectrometric analysis and the following spectra for A, B, and C was obtained. Draw the structure of B and C and match all three compounds to the correct spectra. Relative Intensity Relative Intensity 100 HS-NJ-0547 80 60 31 20 S1 84 M+ absent 10 30 40 50 60 70 80 90 100 100- MS2016-05353CM 80- 60 40 20 135 137 S2 164 166 0-m 25 50 75 100 125 150 m/z 60 100 MS-NJ-09-43 40 20 20 80 45 S3 25 50 75 100 125 150 175 m/z
Part II. Given two isomers: 2-methylpentane (A) and 2,2-dimethyl butane (B) answer the following: (a) match structures of isomers given their mass spectra below (spectra A and spectra B) (b) Draw the fragments given the following prominent peaks from each spectrum: Spectra A m/2 =43 and 1/2-57 spectra B m/2 = 43 (c) why is 1/2=57 peak in spectrum A more intense compared to the same peak in spectrum B. Relative abundance Relative abundance 100 A 50 29 29 0 10 -0 -0 100 B 50 720 30 41 43 57 71 4-0 40 50 60 70 m/z 43 57 8-0 m/z = 86 M 90 100 71 m/z = 86 M -O 0 10 20 30 40 50 60 70 80 -88 m/z 90 100
Part IV. C6H5 CH2CH2OH is an aromatic compound which was subjected to Electron Ionization - mass spectrometry (El-MS) analysis. Prominent m/2 values: m/2 = 104 and m/2 = 9) was obtained. Draw the structures of these fragments.

Chapter 12 Solutions

EBK ORGANIC CHEMISTRY

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