Following are structural formulas, dipole moments, and 1

Organic Chemistry | 6th Edition | ISBN: 9780840054982 | Authors: William H. Brown and Lawrence S. Brown

Problem 13.14 Chapter 13

Organic Chemistry | 6th Edition

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Organic Chemistry | 6th Edition | ISBN: 9780840054982 | Authors: William H. Brown and Lawrence S. Brown

Organic Chemistry | 6th Edition

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Problem 13.14

Following are structural formulas, dipole moments, and 1 H-NMR chemical shifts for acetonitrile, fl uoromethane, and chloromethane. CH3C#N CH3F CH3Cl Acetonitrile Fluoromethane Chloromethane 3.92 D 1.85 D 1.87 D d 1.97 d 4.26 d 3.05 (a) How do you account for the fact that the dipole moments of fl uoromethane and chloromethane are almost identical even though fl uorine is considerably more electronegative than chlorine? (b) How do you account for the fact that the dipole moment of acetonitrile is considerably greater than that of either fl uoromethane or chloromethane? (c) How do you account for the fact that the chemical shift of the methyl hydrogens in acetonitrile is considerably less than that for either fl uoromethane or chloromethane?

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Textbook: Organic Chemistry
Edition: 6
Author: William H. Brown and Lawrence S. Brown
ISBN: 9780840054982

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