CHEM241 Need to Know

Kinetic:

1,2 addition; cold (0°C)

Thermodynamic:

1,4 addition; hot (40°C)

Diene:

electron donating group

Dienophile:

electron withdrawing group

DA; In:

endo; dash

DA; Out:

exo; wedge

Aromatic:

cyclic, conjugated, planar, 4n+2 π e-

Antiaromatic:

cyclic, conjugated, planar, 4n π e-

Nonaromatic:

not cyclic, conjugated or planar

Monosubstituted:

690-710 cm^-1, 730-770 cm^-1

O-disubstituted:

735-770 cm^-1

M-disubstituted:

690-710 cm^-1, 810-850 cm^-1

P-disubstituted:

810-840 cm^-1

1,2,4-trisubstituted:

780-830 cm^-1, 870-900 cm^-1

1,2,3-trisubstituted:

670-720 cm^-1, 750-790 cm^-1

1,3,5-trisubstituted:

660-700 cm^-1, 830-900 cm^-1

Electrophilic Aromatic Substitution:

A.W.:

acid workup

Meta-Directing Deactivator:

Ortho/Para-Directing Deactivator:

Ortho/Para-Directing Activator:

Oxidants:

Na2Cr2O7, H2CrO4, KMnO4

Nucleophilic Aromatic Substitution:

pKa:

-logKa

Degree of Unsaturation:

((2*C) + 2 - H - X + N) / 2

-OH:

3500 cm^-1

IR Absorption (Ether):

1050-1150 cm^-1 (C-O stretch)

NMR (Ether; next to Oxygen):

3.4-4.5 δ

NMR (Epoxide):

2.5-3.5 δ

13C NMR (Ether):

50-80 δ

Reversible Addition Reactions to C=O:

Nu = HO-, H-, R+, RO-, C=N, H2O, ROH, NH2, NR3

Adding K favored for:

aldehydes

EWD favors:

hydride

EDG favors:

C=O

2° Amines give:

enamines as products

3° Amines give:

no reaction

Henderson Hasselbach Equation:

pH = pKa - log [HA]/[A-]

IR:

1710 cm^-1

IR:

1725 cm^-1

IR:

1710 cm^-1

IR:

1740 cm^-1

IR:

1800 cm^-1

IR:

1760, 1820 cm^-1

IR:

1680 cm^-1

IR:

2200-2260 cm^-1

Reaction Rate of Enols:

k[ketone][H+]; independent of x^2

Consequence of enolization is:

racemic mixtures

Kinetic enolate:

Thermodynamic enolate:

pKa:

9.21

pKa:

10.62

pKa:

10.64

pKa:

9.76

pKa:

5.34

pKa:

1.0

pKa:

4.62

pKa:

10.64

IR of NH Stretches:

3300-3500 cm^-1