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In the following dithiane, the correct statement about acidity of Ha and He protons and the reason for the stability of the carbanion formed by deprot
Question

In the following dithiane, the correct statement about acidity of Ha and He protons and the reason for the stability of the carbanion formed by deprotonation is

A.

Ha is more acidic; axial carbanion is delocalized into the σ* orbital of C-S bond

B.

He is more acidic; equatorial carbanion is delocalized into the σ* orbital of C-S bond

C.

Ha is more acidic; axial carbanion is delocalized into the empty 3d orbital of sulfur

D.

He is more acidic; equatorial carbanion is delocalized into the empty 3d orbital of sulfur

Correct option is B

Ha is less acidic than He. The carbanion generated by the removal of Ha will repel more with the lone pairs on sulfur. The carbanion generated by the removal of He will also repel with the lone pairs on sulfur. However, the generated equatorial carbanion is delocalized into the σ* orbital of C-S bond as shown below:

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