Chemistry · Organic Chemistry
In 2-substituted 1,3-dithianes, which of the following statements is correct regarding the acidity of the axial (H a ) and equatorial (H e ) protons at the C-2 position, and the reason for the stability of the resulting carbanion?
Verified Solution4 OptionsUpdated: October 2026👁️1 View
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- 1H a is more acidic; the axial carbanion is stabilized by delocalization into the σ* orbital of the C-S bond
- 2H e is more acidic; the equatorial carbanion is stabilized by delocalization into the σ* orbital of the C-S bond✓
- 3H a is more acidic; the axial carbanion is stabilized by delocalization into the empty 3d orbital of sulfur
- 4H e is more acidic; the equatorial carbanion is stabilized by delocalization into the empty 3d orbital of sulfur
Correct answer
H e is more acidic; the equatorial carbanion is stabilized by delocalization into the σ* orbital of the C-S bond
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