CORRECT order of stability for the following is CH2=CH-, CH3-CH2-, CH C-
- CH C- > CH3-CH2- > CH2=CH-
- CH2=CH- > CH C- > CH3-CH2-
- CH C- > CH2=CH- > CH3-CH2-
- CH3-CH2- > CH2=CH- > CH C-
Answer
(3) CH C- > CH2=CH- > CH3-CH2-
Solution
The stability of a carbanion increases with the s-character of the orbital holding the lone pair, because an orbital with more s-character keeps the electron pair closer to the nucleus (higher electronegativity of carbon).
CH C-: sp (50 % s) > CH2=CH-: sp2 (33 % s) > CH3-CH2-: sp3 (25 % s)
In addition, the ethyl carbanion is destabilised by the +I effect of the methyl group.
Stability: CH C- > CH2=CH- > CH3-CH2-
(This is also the order of acidity of the parent hydrocarbons: ethyne > ethene > ethane.)
Answer: (3)