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Can NaOH be good nucleophile?

Answer 1

Hydroxide anion can be an excellent nucleophile.

We know that a nucleophile is an electron pair donor. The #HO^-# anion can donate electron pairs and make a (strong) #C-O# bond.

#HO^(-)Na^(+) + RCH_2Cl rarr RCH_2OH + NaCldarr#

The nucleophilicity of the hydroxide is increased in non-aqueous solution in relation to its activity in water. In water, hydrogen bonding interactions stabilize the anion; no such stabilization is provided in any organic solvent that can raise it. Elimination is an alternate mechanism for alkyl halides.

#RCH_2CH_2Cl + NaOH rarr RCH=CH_2 + NaCl#

The precipitation of sodium chloride provides a thermodynamic driving force in both cases, and it is evident that the conditions and the substrate will influence whether substitution or elimination occurs. The chemist conducts the experiment FIRST, then justifies the outcomes based on the conditions and reagents.

Would you consider alkoxide, #RO^-#, to be a good potential nucleophile?

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Answer 2

Elias Aguila

Yes, NaOH can act as a nucleophile, particularly in reactions where it donates the hydroxide ion (OH-) as a nucleophile. This is common in organic chemistry reactions, such as SN2 (substitution nucleophilic bimolecular) reactions.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.