Why is it that D hydrogens have a higher chemical shift than the E hydrogens? Aren't the D hydrogens less shielded than the E hydrogens which have carbons surrounding on both sides? And less shielding means higher chemical shift required?

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter11: Alkanes
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Problem 11.24P
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Why is it that D hydrogens have a higher chemical shift than the E hydrogens?

Aren't the D hydrogens less shielded than the E hydrogens which have carbons surrounding on both sides? And less shielding means higher chemical shift required?

d
H
H
d
c=c
f
CH3
CH₂CH3
e g
Isomer B
d = 84.7 (singlet, 2H)
e = 8 2.0 (quartet, 2H)
f = 81.7 (singlet, 3H)
g= 81.0 (triplet, 3H)
Transcribed Image Text:d H H d c=c f CH3 CH₂CH3 e g Isomer B d = 84.7 (singlet, 2H) e = 8 2.0 (quartet, 2H) f = 81.7 (singlet, 3H) g= 81.0 (triplet, 3H)
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