20 Chapter Reagents Acid Chloride

Reactivity Ladder

Acid Chloride Synthesis:

SOCl2 (Thinoyl Chlroide)

1) S from Thionyl Chloride binds to Carbonyl O and Cl- leaves

2) Cl- attacks C of Carbonyl to get O to neutral charge

3) 3 way arrow,

• S-Cl attacks Hydrogen

• -H forms Carbonyl

• SO2 leaves as L.G.

4) Acid Chloride, SO2, and HCl form

1) Reagent: Anhydride Anion

Acyl Chloride → Anhydride

2) Reagent: H2O, Pyradine

Acid Chloride → Carboxylic Acid

3) Reagent:

1) R’HO

2) Pyridine

Acid Chloride → Ester

4) Reagent:
NH3 (2 equiv)

Acid Chloride → 1° Amide

5) Reagent

H3C-NH2 (2 equiv)

Acid Chloride → 2 ° Amide

6) Reagent

H3C-NH-CH3 (2 equiv)

Acid Chloride → 3° Amide

Anhydride Reactions

1) R-OH, Pyridine

Anhydride → Ester

2) H2O, Pyr

Anhydride → Carboxylic Acid

3) R-NH2 (2 equiv)

Anhydride → 2° Amide

Ester Reactions

1) H3O+

Ester → Carboxylic Acid

2) NaOH-, H2O

Ester → Carboxylate Anion

3) NH3

Ester → Amide

Carboxylic Acid Reactions

1) R-OH with Acid Catalyst (H2SO4)

Fischer Esterification

Carboxylic Acid → Ester

1) H2SO4 donates protone to CARBONYL

2) Form RESONANCE and Protonated Carboxylic Acid

3) Remove H from Ester O

4) Add H to OH to form good L.G

5) H2O leaves as Good L.G

6) Resonance to form Carbonyl with OH

7) Deprotonate H in OH

8) Form Ester Final Product with H2O

1T) TRICK Fischer Esterification

2) Reagent:

1) NH3

2) heat

Carboxylic Acid → Amide

3)
1) R-NH-R, DCC

Carboxylic Acid → Amide

4) Heat

Dicarboxylic Acid → Cyclic Anhydride

Amide Reactions

1) H3O+

Amide → Carboxylic Acid + Ammonium Ion

2) H2O, OH-

Amide → Carboxylate + Amine