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​The major product formed in the following reaction sequence is
Question


The major product formed in the following reaction sequence is

A.

B.

C.

D.

Correct option is D

​The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine and an azodicarboxylate such as diethyl azodicarboxylate (DEAD) or diisopropyl azodicarboxylate (DIAD). In a typical protocol, one dissolves the alcohol, the carboxylic acid, and triphenylphosphine in tetrahydrofuran or other suitable solvent (e.g. diethyl ether), cool to 0 °C using an ice-bath, slowly add the DEAD dissolved in THF, then stir at room temperature for several hours. The alcohol reacts with the phosphine to create a good leaving group then undergoes an inversion of stereochemistry in classic SN2 fashion as the nucleophile displaces it.

​The reaction mechanism of the Mitsunobu reaction is fairly complex. 

Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5. The formation of the ion pair 5 is very fast.

The second phase of the mechanism is proposed to be phosphorus-centered, the DEAD having been converted to the hydrazine.

Cs2CO3 abstracts one acidic proton giving an anion. The resulting anion undergoes an intramolecular SN2 displacement reaction and gives a cyclized product. In the last step, PhSH acts as a nucleophile


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