Question
CORRECT order of stability for the following is CH _ 2 = CH ^ - , CH _ 3 - CH _ 2 ^ - , CH C ^ -
CORRECT order of stability for the following is CH _ 2 = CH ^ - , CH _ 3 - CH _ 2 ^ - , CH C ^ -
B. CH C ^ - > CH _ 2 = CH ^ - > CH _ 3 - CH _ 2 ^ -
Carbanion stability is determined by the s-character of the hybrid orbital bearing the negative charge. The acetylide anion CH C^- has the carbanion on an sp hybridized carbon (50% s-character), providing optimal stabilization through efficient overlap with the charged orbital. The vinyl anion CH_2 = CH^- has the carbanion on an sp² hybridized carbon (33% s-character), offering moderate stabilization. The primary alkyl anion CH_3 - CH_2^- has the carbanion on an sp³ hybridized carbon (25% s-character), providing the least stabilization. Greater s-character enables better penetration of the nucleus and enhanced stabilization of the negative charge. Therefore, the order is CH C^- > CH_2 = CH^- > CH_3 - CH_2^-.
Related: Chemistry — General Organic Chemistry · All PYQ Banks