ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY
4th Edition
ISBN: 9781119761105
Author: Klein
Publisher: WILEY
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Chapter 22, Problem 64PP

 (a)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are given and used as the reaction conditions in the given reactions.  This reaction is called Hofmann elimination.  The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternary ammonium salt which is a excellent leaving group.  After treatment with strong base, aqueous silver oxide and heat, quaternary ammonium salt gives alkenes.  Alkene formation involves in E2 elimination.  Through E2 elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 22, Problem 64PP , additional homework tip  1

To find: The major product of compound (a) in Hofmann elimination

Draw and analyze the structure of the compound (a)

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 22, Problem 64PP , additional homework tip  2

(b)

Interpretation Introduction

Interpretation: The major products are to be found when the given compounds are treated with excess methyl iodide followed by aqueous silver oxide and heat.

Concept Introduction:

The reagents such as methyl iodide and silver oxide are given and used as the reaction conditions in the given reactions.  This reaction is called Hofmann elimination.  The amines undergo exhaustive alkylation in the presence of excess methyl iodide producing quaternary ammonium salt which is a excellent leaving group.  After treatment with strong base, aqueous silver oxide and heat, quaternary ammonium salt gives alkenes.  Alkene formation involves in E2 elimination.  Through E2 elimination, the major product is less substituted alkene with trace amount of more substituted alkene.

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 22, Problem 64PP , additional homework tip  3

To find: The major product of the compound (b) in Hofmann elimination

Draw and analyze the structure of the compound (b)

ORGANIC CHEMISTRY-PRINT (LL)-W/WILEY, Chapter 22, Problem 64PP , additional homework tip  4

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(a) Verify that the lattice energies of the alkali metal iodides are inversely proportional to the distances between the ions in MI (M = alkali metal) by plotting the lattice energies given below against the internuclear distances dMI. Is the correlation good? Would a better fit be obtained by plotting the lattice energies as a function of (1 — d*/d)/d, as theoretically suggested, with d* = 34.5 pm? You must use a standard graphing program to plot the graph. It generates an equation for the line and calculates a correlation coefficient. (b) From the graph obtained in (a), estimate the lattice energy of silver iodide. (c) Compare the results of (b) with the experimental value of 886 kJ/mol. If they do not agree, explain the deviation.

Chapter 22 Solutions

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