Acetonitrile (CH3CN) has resonance at 1.97 ppm, whereas methyl chloride (CH3Cl) has resonance at 3.05 ppm, even though the dipole moment of acetonitrile is 3.92 D and that of methyl chloride is only 1.85 D. The larger dipole moment for the cyano group suggests that the electronegativity of this group is greater than that of the chlorine atom. Explain why the methyl hydrogens on acetonitrile are actually more shielded than those in methyl chloride, in contrast with the results expected on the basis of electronegativity

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter15: Benzene And Aromaticity
Section15.SE: Something Extra
Problem 17VC: Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon (μ = 1.0...
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Acetonitrile (CH3CN) has resonance at 1.97 ppm, whereas methyl chloride (CH3Cl) has resonance at 3.05 ppm, even though the dipole moment of acetonitrile is 3.92 D and that of methyl chloride is only 1.85 D. The larger dipole moment for the cyano group suggests that the electronegativity of this group is greater than that of the chlorine atom. Explain why the methyl hydrogens on acetonitrile are actually more shielded than those in methyl chloride, in contrast with the results expected on the basis of electronegativity

 

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