CHCl3 (Chloroform)

1. Lab preparation:

1.1. A) From ethanol (CH3-CH2-OH) StepI: CaOCl2+H2O → Ca(OH)2+Cl2 StepII: CH3-CH2-OH+Cl2 → CH3-CHO+HCl StepIII: CH3-CHO+CL2 → CCl3-CHO +HCl StepIV: CCl3-CHO+Ca(OH)2 → CHCL3+(CHCOO)2Ca

1.2. B) From propanone (Acetone) StepI: CaOCl2+H2O → Ca(OH)2+Cl2 StepII: CH3-COO-CH3+CL2 -𝛥→ CCl3-COO-CH3+HCl StepIII: CCl3-COO-CH3+Ca(OH)2 -𝛥→ CHCl3+(CH3COO)2Ca

2. Chemical properties

2.1. 1. With air/O2/oxidation: CHCL3+O2 -hv→ COCl2+HCL COCl2 is called phosgene gas which is a highly poisonous gas. common name: cabonyl chloride IUPAC name: Chloromethanoyl chloride

2.2. 2. With Cl2 (Chlorination) CHCl3+Cl2 -hv→ CCl4+HCl

2.3. 3. Reduction a. Partial or acidic medium CHCl3+2[H] -Zn/HCl→ CH2Cl2+HCL b. Complete (neutral medium) CHCl3+6[H] -Zn/H2O(steam),𝛥→ CH4+HCL

2.4. 4. With aq.KOH and aq.NaOH CHCl3+KOH → HCOOK+KCl+H2O CHCl3+NaOH → HCOONa+NaCl+H2O

2.5. 5. With c.HNO3 CHCl3+HNO3 → CCl3-NO2+H2O The industrial name of CCl3-NO2 is chloropicrin. Its common name is tear gas or Nitrochloroform. It is used as insecticide. Its IUPAC name is trichloronitromethane

2.6. 6. With acetone CH3-COOH-CH3+H-CCl3

2.7. 7. With Ag powder CHCl3+Ag → CH≡CH+AgCl

2.8. 8. With 1°-amine (Isocyanide test ICT) R-NH2+CHCl3+KOH → R-NC+KCl+H2O

2.9. 9. With phenol (Reimer-Tiemann's rxn): When phenol is heated with chloroform in presence of KOH, it gives an intermediate product which on acidificationives o-salicyaldehyde. Rxn: click on the link

2.10. 10. With AgNO3: CHCl3+AgNO3 → no rxn AgCl is a covalent compuound. so it doesn't give Cl- But if AgCl is contaminated by COCl3, it gives AgCl. CHCl3+O2 -hv→COCl2+HCl -AgNO3 → AgCl↓+ HNO3