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14 Cards in this Set

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Delocalized Electrons

Shared by 3 or more atoms. It is the result from the P orbital of one Atom overlapping the porbitals of 2 adjacent atoms.

Rules for drawing resonance contributors

1. Only electron's move. Atoms never move. 2. only pi electrons and lone Pair electrons can move. Sigma electrons never move. 3. The total number of electrons in the molecule does not change. 4. Electrons always move to an SP2 or SP Atom; SP3 atoms cannot accept electrons.

Separated charges stability

The predicted Stability of a compound with separated charges is less than the stability of a compound without separated charges.

Features that decrease the predicted stability

1. An Atom with an incomplete octet. 2. A negative charge that is not on the most electronegative atom. 3. a positive charge that is on an electronegative Atom. 4. separated charges.

Delocalization Energy

The delocalization energy is the extra stability of a compound has as a result of having deocalized Electron.

This energy is also called resonance energy. The resonance hybrid is more stable than any of its resonance contributors are predicted to be.

Isolated Diene

Double bonds are separated by more than one single bond.

The smaller the heat of hydrogenation the more stable the compound.

Conjugated Diene

Double bonds are separated by one single bond.

more stable than an isolated dienes. Have delocalized electrons.

Allyl,benzyl,allylic, Benzylic cation

Resonance contributor to allylic cation

Resonance contributor to Benzylic Cation.

Relative stabilities of Carbocation

In decreasing order Benzel cation= Allyl cation=tertiary carbocation secondary carbocation, primary carbocation, methyl cation, vinyl cation

Delocalized electrons affect PKA values

A carboxylic acid is a stronger acid than an alcohol because of inductive electron withdraw and electron delocalization.

Electron donation

Destabilizes the base by increasing the electron density on the oxygen

Decreases acidity.

Electron Withdrawal

stabilizes the base by decreasing the Electron density on the oxygen.

Increases acidity.