General Reagents Chapter 17

Oxidation. (to Carboxylic acid or anion) Cyclic Alkanes -> Carboxylic acids Ph-R -> Ph-C(=O)-O (Will replace the most acid H or the group on the benzene ring) Aldehyde (C=O)-H -> Carboxylic Acid Anion (C=O)-O- (Could then be protonated) Alcohol (C-OH) -> Carboxylic Acid (C=O) (Only works with primary alcohols)

Oxidation. (to Carboxylic acid anion) Aldehyde (C=O)-H -> Carboxylic Acid Anion (C=O)-O-

Oxidation. (to Carboxylic acid anion) Aldehyde (C=O)-H -> Carboxylic Acid Anion (C=O)-O-

Oxidation. (to Carboxylic acid) Aldehyde (C=O)-H -> Carboxylic Acids (C=O)-OH Alcohol (C-OH) -> Carboxylic Acids (C=O)-OH

Same as CrO3. Oxidation to Carboxylic Acid

Same as CrO3. Oxidation to Carboxylic Acid

Fisher Esterification or Transesterification. (Hydrogen of the Alcohol protonates the Oxygen or Chloride and creates a leaving group, the OR of the Alcohol replaces the leaving group)

Aminolysis. (Hydrogen of the Amine protonates the Oxygen or Chloride and creates a leaving group, the NR2 of the Amine replaces the leaving group)

Grignard. Amides with N-H have their hydrogen removed and become anions CO2 becomes Carboxylic Acid (C=O)-OH Carboxylic Acids (C=O)-OH become Carboxylic Acid Anions (C=O)-O- Acid Chlorides (C=O)-Cl, Anhydrides(C=O)-O-(C=O), and Esters (C=O)-O-R become 3* Alcohols

Grignard. Amides with N-H have their hydrogen removed and become anions CO2 becomes Carboxylic Acid (C=O)-OH Carboxylic Acids (C=O)-OH become Carboxylic Acid Anions (C=O)-O- Acid Chlorides (C=O)-Cl, Anhydrides(C=O)-O-(C=O), and Esters (C=O)-O-R become 3* Alcohols (R-)(R-)C(-OH)-R

Reduction. Carboxylic Acids (C=O)-OH, Acid Chlorides (C=O)-Cl, Anhydrides (C=O)-O-(C=O), and Esters (C=O)-O-R become 1* Alcohols (R-C-OH) Amides (C=O)-NR2 become Amines H-(H-)C-NR2 (=O is replaced with -H,-H)

Bulky Reduction Agent. Removes the CL of an Acid chloride, the -O-R of an Ester, or the NR2 of an Amide, changing the molecule to an Aldehyde

Reactions with Carboxylic Acid creates an anion. Reactions with Acid Chloride (C=O)-Cl, Anhydride( C=O)-O-(C=O), Ester(C=O)-O-R, or Amide (C=O)-NR2 creates a Carboxylic Acid (C=O)-OH

Turns Amides (C=O)-NR2 into Carboxylic acids (C=O)-OH

Saponification (Creation of a Carboxylic Acid Anion) Carboxylic Acids (C=O)-OH, Acid Chlorides (C=O)-Cl, Anhydrides (C=O)-O-(C=O), Esters (C=O)-O-R, and Amides (C=O)-NR2 become Carboxylic Acid Anions (C=O)-O-

+ Acid Chloride → Anhydride + Heat → break away from larger compound

The chlorine of the acid chloride is removed and that carbon bonds with the Oxygen of the other substrate, creating an ester or anhydride. + Carboxylic Acids (C=O)-OH -> Anhydrides (C=O)-O-(C=O) + Acid Chlorides (C=O)-Cl -> Esters (C=O)-O-R

Replaces the -OH of a Carboxylic Acid with Chloride, creating an Acid Chloride

Friedel Crafts Acylation. Used with the addition of an acid chloride to make a ketone The Cl of the acid chloride is removed and the resulting molecule bonds onto the substrate