Organic Chemistry 1 Study Guide

Electrophile
Electron Loving
Electron Deficient
Accepts Electrons
Identify Electrophile:
1. Positive charge system can act as an electrophile (NO+, X+, Ph-N2+, etc.)
2. Neutral Molecules are electrophiles
Nucleophile
Nucleus Loving
Electron Rich
Donate Electron
Identify Nucleophile
1. All Negative charges act as nucleophile (H-, OH-, NH2-, X-, etc.)
2. Neutral Molecule WITH central atom having at least one lone pair of electrons
(H2O, NH3)
3. A electron system can act as nucleophile (Ex: Alkene, Alkyne, etc.)
4. Metals
Electronic Effects
Influences Structures, reactivity, or properties of molecules but is neither a traditional
bond nor a steric effect.
Release of e- or attraction of e- :
Resonance Effects
1. Shift of lone pairs of e- and/or bonds of e Inductive Effects
1. Shift of e- in sigma () bonds
Inductive Effects are always weaker than resonance effects b/c e- are more localized in
bonds.
Resonance Effects
Ability to delocalize (SPREAD OUT) charge
Goal is to redistribute the electrons in bonds
Delocalize charge over more than one atom INCREASES stability of charged
species.
Generally, more resonance structures = more stable
Taking electrons from an area that has an excess e- to an area with little electrons
(+ charge)
Most stable resonance forms:
1. Every single atom has an octet
2. Minimize number of charges
CHCl3 is more acidic than CHF3
Mainly for multiple bonds

Resonance Examples

RESONANCE STABILITY RULES OF NEGATIVE CHARGES

RESONANCE STABILITY RULES OF POSITIVE CHARGES

Electronic Effects (continued)

Inductive Effects
o Electronic effects due to polarization of bonds within a molecule or ion

o Electronegativity difference b/w the atoms at either end of bonds

o The effect on electron density in one portion of molecules due to electronwithdrawing or electron-donating groups elsewhere in molecules
o Induction effect of an atom depends on 3 things
1. Electronegativity
The effect on electron density in one portion of a molecule due to
electron-withdrawing or electron-donating groups elsewhere in the
molecule
In a covalent bond between two atoms of unequal
electronegativity, the atom with higher electronegativity withdraws
(pulls) electron density towards itself, causing + and - charges of
the bond dipole
Addition of a electronegative atom causes the molecule to be more
acidic.

2. Bonding Order and Charge

3. Position Within a Structure
o Negative Inductive Effects (-I)
The most electronegative atom will pull the electron away from the other
atoms. However, as you move further AWAY from the most
electronegative atom the electropositivity increases
Electron Withdrawing Effect

o Positive Inductive Effect (+I)

When electropositive atom or group is attached to the terminal of the
carbon chain in a compound, the electrons are DISPLACED away from
the attached atom or group
Electrons want to get as far away as possible from the electropositive
group
Electron releasing effect