While heavily halogenated carbanions are stabilized by inductive effects, why is the trichloromethyl — GOC and Organic Chemistry Basics Chemistry Question
Question
While heavily halogenated carbanions are stabilized by inductive effects, why is the trichloromethyl carbanion ($CCl_3^-$) significantly more stable than the trifluoromethyl carbanion ($CF_3^-$), despite fluorine being more electronegative?
Answer: C
💡 Solution & Explanation
Although F has a stronger $-I$ effect, Cl possesses vacant 3d orbitals. The negative charge on the carbon atom can delocalize into these vacant d-orbitals of adjacent chlorine atoms via $p\pi-d\pi$ back-bonding (resonance), providing substantial stabilization unavailable to $CF_3^-$.
💬Ask on WhatsApp →
Still have doubts about this question?
Send it to our AI chemistry tutor on WhatsApp — gets answered in minutes