How come Na+ is removed from NaOCH2CH3 instead of one of the methyl hydrogens? Isn't the hydrogen easier to remove?

General, Organic, and Biological Chemistry
7th Edition
ISBN:9781285853918
Author:H. Stephen Stoker
Publisher:H. Stephen Stoker
Chapter10: Acids, Bases, And Salts
Section: Chapter Questions
Problem 10.38EP: Using the diagrams shown in Problem 10-37, which of the four acids is the weakest acid?
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How come Na+ is removed from NaOCH2CH3 instead of one of the methyl hydrogens? Isn't the hydrogen easier to remove?

(g)
NAOCH,CH3 +
Cl½CHCH,OH
HOCH,CH3 +
Cl2CHCH2ONa favors
conjugate base
weaker base
PRODUCTS
conjugate acid
weaker acid
stronger base
stronger acid
more stable anion-
2 Cl stabilize anion
Transcribed Image Text:(g) NAOCH,CH3 + Cl½CHCH,OH HOCH,CH3 + Cl2CHCH2ONa favors conjugate base weaker base PRODUCTS conjugate acid weaker acid stronger base stronger acid more stable anion- 2 Cl stabilize anion
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