All Named Reaction In PDF Riemer-Teiman, Parkin’s, Named Reactions – Copy note

Lecture Notes on some important Name Reactions

All Named Reaction In PDF

Riemer-Teiman, Parkin’s, Named Reactions – Copy note

Wurtz Fitting Reaction

                     Wurtz Fitting reaction is a method to prepare alkyl derivative of arene by means of general Wurtz reaction.

C6H5I + 2Na + I-CH3 C6H5CH3 + 2Na

It is just a modification of Wurtz reaction – a method of synthesizing alkanes using alkyl halide and sodium in ether medium.

(e.g. of i) Wurtz Reaction:   

CH3I + 2Na + I-CH3 C2H6 + 2NaI 

Ether medium

 (ii) Fitting Reaction:

C6H5I + 2NaI + I-C6H5 C6H5C6H5+ 2NaI

Wurtz Fitting reaction is the combination of these two above reactions – Wurtz reaction and Fitting reaction. Yield is very poor (10 – 5%) due to the formation of many side products.

Mechanism of the Wurtz-Fittig Reaction:

The reaction proceeds via a free radical mechanism in three main steps:

The reaction stops when all radicals are consumed.

Formation of Free Radicals:

• Sodium metal donates an electron to the halides, generating alkyl (R•) and aryl (Ar•) radicals.

R-X+Na→R•+NaX

Ar-X+Na→Ar•+NaXAr

Coupling of Radicals:

• The alkyl and aryl radicals combine to form the desired alkyl-substituted aromatic compound.

R•+Ar•→R-Ar

R•+Ar•→R-Ar(Major product)

Side reactions may occur, leading to R-R (from Wurtz reaction) and Ar-Ar (from Fittig reaction) as byproducts.

Termination:

The reaction stops when all radicals are consumed.

Example:

CH3Br+C6H5Br+2Na→C6H5CH3(Toluene)+2NaBrCH3​Br+C6​H5​Br+2Na→C6​H5​CH3​(Toluene)+2NaBr

Difference from Wurtz & Fittig Reactions:

• Wurtz Reaction: Couples two alkyl halides → Alkane (R-R).
• Fittig Reaction: Couples two aryl halides → Biaryl (Ar-Ar).
• Wurtz-Fittig: Couples one alkyl + one aryl halide → Alkylarene (R-Ar).

Application and Extension:

i) Widely used for polynuclear hydrocarbon

ii) In the synthesis of anthracene:

iii) In the synthesis of Phenanthrene

Wurtz Fitting Reaction

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