Monday 11 May 2015

organic chemistry - How to determine the most stable carbanion?



Which of the following carbanions is the most stable?


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I think the answer is either a or c, as in d there are no chances for the carbanion to have its charge become less. In b I think there is a + inductive effect due to methyl group which gives it more negative charge.


The ones left are a and c. Nitrogen is an electronegative element so it might lessen the charge on the carbanion, but in both a and c the carbanion is same distance from it. I am unable to reason out it from here.



Answer



Wikipedia says:



The stability and reactivity of a carbanion is determined by several factors. These include


1)The inductive effect. Electronegative atoms adjacent to the charge will stabilize the charge;


2)Hybridization of the charge-bearing atom. The greater the s-character of the charge-bearing atom, the more stable the anion;


3)The extent of conjugation of the anion. Resonance effects can stabilize the anion. This is especially true when the anion is stabilized as a result of aromaticity.




You can see that point 3) is not relevant here. We do not have a conjugated system, nor is there any chance for resonance.


Keeping in mind point 1), the $\ce{N^+}$ has a $\ce{-I}$ effect, but inductive effect reduces over distance. The negative charges in options a), b) and d) are either in the meta or para position.


Also, remember that $\ce{+I}$ effect destabilises the carbanion.


In c), the carbanion is primary, but in a), it is secondary. Primary carbanions are more stable due to lesser $\ce{+I}$ effect.


So your answer is c).


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