Biotin; an essential vitamin was developed by Hoffmann-La Roche by compound 1. Conversion of 1 to 4 involves: Removal of OH group Replacement with Cl group from SOCl 2 Formation of intermediate 2 Liberation of SO 2 gas and chloride ion The Conversion of 2 to 3 by inversion of configuration but X-ray crystallography confirms the retention of configuration. The mechanism is to be interpreted for the given steps. Concept introduction: The chemical transformation can be shown by the arrow pushing method in which the curved arrows show the movement of electrons or protons. In a chemical reaction , the attack of reagent (electrophile or nucleophile), and loss of leaving group can easily be determined with the help of arrow pushing patterns.

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Chapter 7, Problem 112CP

Interpretation Introduction

Interpretation: Biotin; an essential vitamin was developed by Hoffmann-La Roche by compound 1. Conversion of 1 to 4 involves:

Removal of OH group

Replacement with Cl group from SOCl2

Formation of intermediate 2

Liberation of SO2 gas and chloride ion

The Conversion of 2 to 3 by inversion of configuration but X-ray crystallography confirms the retention of configuration. The mechanism is to be interpreted for the given steps.

Concept introduction: The chemical transformation can be shown by the arrow pushing method in which the curved arrows show the movement of electrons or protons. In a chemical reaction, the attack of reagent (electrophile or nucleophile), and loss of leaving group can easily be determined with the help of arrow pushing patterns.

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