Omega oxidation

• Where
• What happens?

• ending alkanes and cycloalkanes at least 3 C long
• Gains an OH

Allylic Oxydation

• Where
• What

• Carbon attached to alkene
• H becomes OH

Benzylic Oxydation

• Where
• What

• 1 carbon away from benzene ring
• H becomes OH

R-SH

• PKA
• Interactions
• Ionized?

Thiol

• Acidic PKA 10-11
• H bond (D), Dipole-Dipole, Ion-Dipole
• Not ionized
  

Benzene-OH

• PKA
• Interactions
• Ionized?

Phenol

• Acidic PKA 10
• H Bonding (A+D), Dipole-Dipole            
• Unionized

Benzene-SH

• PKA
• Interactions
• Ionized?

Thiophenol

• Acidic PKA 6.6
• H bond (D), Dipole-Dipole, Ion-Dipole
• Ionized if PH >6.6

Alcohols

• Interactions
• Ionized?

• H Bonding (A+D), Dipole-Dipole, Ion-Dipole
• NA

R-O-R

• Interactions
• Ionized?

Ether

• H Bonding (A), Dipole-Dipole, Ion-Dipole
• NA

R-S-R

• Interactions
• Ionized?

Thioether

• Hydrophobic interactions
• NA

Interacts with Methionine

Aromatic Hydroxylation

• Where
• What happens

• Ortho or Para to a substituant
• Gains an OH

1. Omega/Omega -1 Oxidation
2. Peroxidation/Epoxidation
3. Allylic Oxidation
4. Aromatic Hydroxylation
5. Benzylic Oxidation
6. Oxidative O-Dealkylation
7. S-Dealkylation

Amines

• PKA

• 9-11

Guanidine

• PKA

• 10

Aniline

• PKA

• 4-5

Amidine

• PKA

• 8-9

Imidazole

• PKA

• 6

• 1*, 2* amines
• Side with N gains an H, other side (which has an H) =O

• T Amines, T cyclic Amines
• N gains an O^-, N becomes N⁺

• Primary Amines
• Side of N gets H, other side (which has an H) Aldehyde

Glucuronidation

• Who
• What?

• OH, 1*/2* OH, Amine, Aniline,
• Lose H gain gluc

Acetylation

• Who
• What?

• 1* Amines, Aromatic 1* is ok
• H -> Ketone H₃C-C=O

Sulfation

• Who
• What

• Phenol
• H -> SO₃^-

O-Methylation

• Who
• What

• Phenol, Catechol (must designate)
• An H -> CH₃

Amino Acid conjugation

• Who
• What

• Carboxylic acid
• OH -> amine part of AA.

1. Glucuronidation
2. Acetylation
3. Sulfation
4. O-Methylation
5. Amino Acid conjugation

Ester Hydrolysis

• Who
• What

• Ester
• cut between carbonyl and O 

Ester -> carboxylic acid + Alcohol

Amide Hydrolysis

• Who
• What

• Esters
• cut between carbonyl and N

Ester -> amine + Carboxylic acid.

1. Oxidative N-dealkylation
2. N-Oxidation
3. Oxidative deamination
4. Ester hydrolysis
5. Amide hydrolysis

• Aldehyde
• Ester

• Gluc
• Acetylation (1* only)

• Gluc
• Sulfation
• O-Methylation (phenol or catechol)

• Gluc
• Amino acid conjugation

• Gluc (1*,2* only)

Phenol

Thiophenol

Carboxylic acid

Sulfonamide (Unsub & monosub)

Sulfonylurea (Unsub)

Sulfonate

Phosphonate

Phosphate

Amines

Aniline

Amidine

Guanidine

Imine

Oxime

Hydrazine

• H bond
• Ion-Dipole
• Ionic

Imine

PKA

Oxime

PKA

Hydrazine

PKA

Azide

PKA

1. Omega/omega -1
2. Allylic
3. Benzylic
4. Alcohol
5. N
6. epoxidation/peroxidation

1. Amide Hydrolysis
2. Ester Hydrolysis

1. Oxidative O Dealkylation
2. Oxidative N Dealkylation
3. S dealkylation
4. Oxidative deamination

• Glycine
• Glutamine
• Arginine
• Taurine