bond to the carbon atom:
+ RRNu +
Leaving group
Heterolysis occurs here
Nu − X X −
Nucleophile
- When does the C–X bond break?
- Does it break at the same time that the new bond between the nucleophile and
the carbon forms?
+ R Nu R X Nu R+
δ−
Nu − X X −
δ−
2) Does the C–X bond break first?
R X R+ + X −
And then
Nu − + R+ Nu R
6.4 NUCLEOPHILES
- A nucleophile is a reagent that seeks positive center.
- The word nucleophile comes from nucleus, the positive part of an atom, plus
- phile from Greek word philos meaning to love.
C X
δ+> δ− The electronegative halogen
polarizes the C−X bond.
This is the postive center
that the nuceophile seeks.
- A nucleophile is any negative ion or any neutral molecule that has at least one
unshared electron pair.
- General Reaction for Nucleophilic Substitution of an Alkyl Halide by
Hydroxide Ion
