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Propose a mechanism to account for this rearrangement

Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote ISBN: 9781133952848 483

Solution for problem 11.25 Chapter 11

Organic Chemistry | 7th Edition

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Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Organic Chemistry | 7th Edition

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11
5
Problem 11.25

Propose a mechanism to account for this rearrangement.

Step-by-Step Solution:
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Notes Week 24-28 Friday, October 21, 2016 7:26 PM 11.3 Continued: • Dispersion Force (London force): intermolecularforce present in all moleculesand atoms ○ Result of fluctuations in the electrondistribution within moleculesor atoms. ○ Electrons in an atom or molecule may at any instant be unequally distributed ○ The magnitude of the dispersion force depends on how easily the electrons in the atom or moleculecan move or polarize in response to an instantaneousdipole.  Larger electron cloud results in larger dispersion force  If all other factors are constant, dispersion force increaseswith molar mass  Shape of molecule can also have impact on dispersion force □ Longer molecules have greater dispersion because there's more area for contact betweenmolecules □ Small or round moleculeshave lower dispersion because there's smaller area for contact  Boiling point is a reflection of how great dispersion forces are □ Greater the dispersion, higher the boiling point □ Lower the dispersion, lower the boiling point • Dipole-Dipole Force: existsin all moleculesthat are polar ○ Polar molecules have electron compacted regions and electronlacking regions, resulting in permanently charged regions ○ Polar molecules have higher melting and boiling points than nonpolar moleculesof similar molar mass.

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Chapter 11, Problem 11.25 is Solved
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Textbook: Organic Chemistry
Edition: 7
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
ISBN: 9781133952848

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Propose a mechanism to account for this rearrangement