# How do you determine if you have an electrophile or a nucleophile?

May 31, 2016

It's not always a black/white "it's definitely this or that", but...

PROPERTIES OF TYPICAL NUCLEOPHILE

• Should be relatively sterically unhindered for nucleophilic behavior.

Example:

• If negatively-charged, consider the possibility of either basic behavior or nucleophilic behavior.

Example:

• If it has a lone pair of electrons, consider the possibility of either basic behavior or nucleophilic behavior. If so, then it should definitely be in an aprotic solvent.

Example:

• stackrel(..)("N")"H"_3
• ${\text{R"stackrel(..)("N")"H}}_{2}$
• etc.
• Should be in an aprotic solvent, especially if the nucleophile is negatively-charged or has a lone pair (could undesirably steal a proton and deactivate itself):

Example:

AND has a conjugate acid $\text{pKa}$ higher than the $\text{pKa}$ of the solvent (remember the equilibrium lies on the side of the weaker acid, so the higher conjugate acid $\text{pKa}$ means the equilibrium would favor protonating the nucleophile and deactivating it):

Example:

PROPERTIES OF TYPICAL ELECTROPHILE

• If positively-charged, generally it makes a nice electrophile.

Example:

• If a particular atom would possess a partial positive formal charge in a fairly polar bond:

Examples:

• $\text{HCl}$
• $\text{HBr}$
• $\text{HI}$
• etc.

or if the molecule is polarizable so that the electron distribution can be disturbed towards the more electronegative atom (away from the nucleophile):

Examples:

• $\text{HCl}$
• $\text{HBr}$
• $\text{HI}$
• ${\text{Br}}_{2}$
• ${\text{I}}_{2}$
• etc.

then it is probably an electrophile.