What stabilizes a carbocation in a nucleophilic substitution reactions?

Essentially, it is the adjacent atoms or groups attached to the central carbon atom which have the ability to stabilise or destabilise a carbocation. The formation of this carbocation is what determines the rate of the reaction (as the Rate Determining Step), therefore the level of stability of the carbocation intermediate will determine how quickly or slowly this intermediate is formed; a stable intermediate will form quicker than a more unstable one. 

Large bulky alky groups possess electron donating (ED) effects, meaning it pushes electron density onto the central positively charged carbon atom through resonance. The fewer ED groups which are attached to the central carbon the less stability will be given to the carbocation via resonance. A general rule of thumb in order of stability: tertiary carbon > secondary > primary. Also important to note that groups such as nitro or carbonyl groups will have the opposite effect as they possess a electron withdrawing (EW) effect. 

AH

Related Chemistry A Level answers

All answers ▸

What is the structure of benzene?


Without calculation, predict (giving you reasoning) whether the entropy change for the following reaction will be significantly positive, significantly negative or approximately zero: MgO(s) + CO2 (g) --> MgCO3 (s)


Explain the trend in reactivity of group 2 elements with water as you go down the group.


Alcohol A has the chemical formula CH3CH(OH)CH2CH(CH3)CH3 . Give the IUPAC name for alcohol A.