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40 Cards in this Set

  • Front
  • Back

Hybridization

generate molecular orbitals involved in bonding

Unhybridized p-orbitals make

Pi bonds

Hybrid oribals on carbon make

Sigma Bonds

Hybridization involves

valence electrons

Pi Bonds overlap

Side to Side

Sigma bond overlap

End to End

Bond strength goes up with

decreasing bond length


*due to % overlap goes up

As distance from nucleus increases

electron orbital will distort and become highly polarizable

Trends on Periodic Table for Electronegativity

More electronegative as move left to right (more protons) and down to up (more subsheilding)

Resonance Hybrid:

Unique singular species

Best Representation of Structure

Resonance Hybrid, more stable more contributes

3 Hyperconjugation of ions

Cation - stabilizing


Anion - destabilizing


Free Radical - stabilizing

Why free radical not nucleophile or electrophile?

Can't donate 2 electrons or accept 2 electrons.

3 Intermolecular forces in order of strength

hydrogen bond, dipole-dipole bond, van der walls

When heat added to molecular ensemble

molecules separate from each other

4 rankings of acidity

1. More Oxygen's more acidic


2. 1>2>3 degree 1 most acidic


3. Most resonance forms


4. Charge + best

2 Rankings of Basic

1. Charge - best


2. localized

4 Ranking Nucleophilic

1. Charge on a Carbon


2. Localized


3. Smallest molecule


4. Charge - best

Isotope pattern for Cl and Br

Cl - 3:1, Br - 1:1

Nuclear Magnetic moments aligned to each other:

Randomly in external field

Orientation after an external magnetic field

Non-random, parallel to anti parallel

Parallel or Anti parallel higher energy and why

Anti, more energy from moving parts

Parallel or Anti parallel more populated by:

Parallel by 1%

RF Field function:

remove net magnetization from equilibrium

RF pulsed on and off, why?

perturbs frequency causing it to excite and pull away from equilibrium

NMR

Nuclear magnetic resonance

TMS 3 points

*reference standard for NMR


*Electron rich


*shielded and upfield

Polar Protic

Have O-H or N-H bond, can hydrogen bond accept only

Polar Aprotic

Lacking O-H or N-H bond, can both donate and accept hydrogens

4 qualities of Transition State

*Short lived


*Partial bond formation/cleavage shown

4 aspects of Concerted Reaction

*Partial formation and cleavage
*Never reactive intermediate


*Require specific transition state geometry


*different geometry possible

Sn2 Properties
CRSSLNPK

*Concerted


*No reactive intermediate


*Stereospecific -inverted


*Want low steric hindrance


*LG = modest


*Nu = anions


*Polar Aprotic


*Second order kinetics

Sn1


CRSSLNPK

*Non-concerted


*Carbocation - involves reactive intermediate


*Non stereospecific


*High Steric Hinderance


*LG =best


*Nu=modest strength


*Polar Protic


*First order kinetics

4 Fates Carbocation

1. React with own LG


2. Attacked by external Nu


3. Alpha proton produces alkene


4. Rearrange and repeat

Carbocation Rearrangements

Less stable to most stable

3 carbocation rearrangements

1. 1-2 hydride shift


2. 1-2 methyd shift


3. Ring Expansion

Saytseff's Rule

More substituted alkene more stable

Intermolecular Reaction

2 body collision

Intramolecular Reaction

within molecule

E2

*Concerted


*Anti pariplanar geometry
*LG must be axial


*LG = good (like Sn2)


*Solvent =polar aprotic - no cations


*Nu/Base=want best steric hindered