pKa Values

Value of HCl

-7

Value of HBr

-9

Value of HI

-10

Value of HF

3.2

Value of H3O+ or ROH

-1.7

Value of alpha C-H of a ketone

19-20

Value of Alkane (single bond C-C)

50

Value of Alkene ( double bond C=C)

44

Value of Alkyne (terminal) [triple bond CC]

25

Allyle Proton

42

Value of NH2 , RNH2 , R2NH

35-38

Value of NH4+ , RNH3 +

9 - 10

What does a high pKa tell you?

Weak acid → Strong Conj. Base

What does a low pKa tell you?

Strong Acid → Weak Conj. Base

Equation of pH

..pH = pKa + log ([A-] / [HA+])

Equation of pKa

..pKa = -log Ka

What does SERHI stand for

Size, Electronegativity, Resonance, Hybridization, Induction

What did Henry Boris Kagan do?

Discovered the non-linear effects and autocatalysis in asymmetric organic synthesis

What did Kenso Soai do?

Discovered the non-linear effects and autocatalysis in asymmetric organic synthesis

What does 2^n count?

Counts the amount of stereoisomers using chiral stereocenters in a compound

Bronsted-Lowry Acid?

Proton Donor

Bronsted-Lowry Base?

Proton Acceptor

Lewis Acid?

Electron-pair acceptor

Lewis Base?

Electron-pair donor

What does it mean when pH = pKa?

[A-] = [HA+]

.pH < pKa

Acid form dominates

.pH > pKa

Conjugate Base Dominates

Carboxylic Acid pKa R - C = O

I

O -

4 - 5

Gibbs Free Energy Equation and favoring

ΔG = ΔH - TΔS

• When G is less than 0, favors products

• When G is more than 0, favors reactants

Gibbs Free Energy in relation to Keq

ΔG° = -RT ln Keq

• Negative G means Keq > 1

• Positive G means Keq < 1

R and S chirality directions

R : Clockwise

S: Counterclockwise

Constitutional Isomers

Same molecular formula, different bonding

Stereoisomers

Same connectivity, different arrangements in space

Enantiomers

Non-super impossible mirror images

• R,S and S,R

Diastereomers

Stereoisomers that are not mirror images

• R,S and S,S

Conformational v. Configurational

Conformational: Rotation about single bonds

Configurational: Requires Breaking Bonds

Me so Compounds

Stereocenters but is a achiral compound due to an internal plane of symmetry

Decalin

Two bridgehead hygrogens between two rings

• Cis: can flip!

• Trans: CANNOT flip !