Lead Tetraacetate

Lead Tetraacetate

Lead Tetraacetate (LTA)

Lead Tetraacetate
Very Important for B.Sc., M.Sc., CSIR, GATE, JAM, SLET, and Other Entrance Exams. Preparation
Lead Tetraacetate may be prepared by gradually adding red lead with stirring to a mixture of acetic acid and acetic anhydride at 55° to 88°C temperature.
preparation of lead tetraacetate
Uses
1. As Oxidizing Agent
With Monohydric Alcohols
Primary and Secondary alcohols converted into Aldehydes and Ketones respectively.
LTA with monohydric alcohol

With Dihydric Alcohols
Oxidation of Dihydric Alcohols with LTA
Alcohols having δ-hydrogen may be cyclized.
Oxidation of Alcohols having &delta hydrogen with LTA

Lead Tetraacetate also oxidize compounds having nitrogen and oxygen -nitrogen on adjacent carbon atoms.
Oxidation of Compound having nitrogen with LTA

Lead Tetraacetate also oxidize hydroxyquinone to quinone.
Oxidation of hydroxyquinone with LTA

Oxidation of α-hydroxy acids and α-keto acids to ketones and acids respectively.
Oxidation of hydroxyquinone with LTA
-COOH with LTA generally gives decarboxylated product but when double bond present nearby, lactone is formed and when β-H is present then alkene is formed.
Oxidation of monobasic acid derivatives with LTA

Succinic acid derivatives undergoes bisdecarboxylation with Lead Tetraacetate and gives alkenes.
Oxidation of Succinic acid derivatives with LTA

Malonic acid derivatives undergoes bisdecarboxylation with Lead Tetraacetate and gives Ketones.
Oxidation of malonic acid derivatives with LTA

Oxidation of Aromatic primary amines with lead tetraacetate gives Azo compounds.
Aromatic primary amines with lead tetraacetate
2. As Methylating and Acetoxylating Agent
As Methylating Agent
Direct methylation takes place when boiled with LTA and glacial AcOH.
Benzene gives Taulene and TNB gives TNT
methylation with LTA

As Acetoxylation Agent
Molecules having enolizable keto group undergoes acetoxylation with lead tetraacetate.
In cyclo alkenes, both the double bond and allylic positions are actoxylated.
acetoxylation with LTA

Summary
1. It is a strong Oxidizing agent
2. It ia a source of Acetyloxy and Methyl group
3. It convert Alkenes to γ Lactones
4. It oxidize alcohols carrying a δ proton to cyclic ethers
5. It make oxidative cleavage of certain allyl alcohols in conjugation with ozone
6. It converts 1,2-diol to corresponding aldehydes or ketones
7. It also convert Acetophenone to Pheylacetic acid
8. Decarboxylation of Carboxylic acids to Alkyl halide with LiCl or other Li-salts (Kochi Reaction)
Important Reactions with Lead Tetraacetate
Important Reactions of Lead Tetraacetate
Important Reactions of Lead Tetraacetate