Chapter 10, Problem 37DSP

Interpretation Introduction

Interpretation:

The truestatements about the reaction shownare to be determined.

Concept Introduction:

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Tributyltin hydride is a reducing agent. It converts an alkyl halide to an alkane through the formation of an alkyl free radical.This free radical can undergo intramolecular cyclization.

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The attack is termed exo if the radical in the resulting intermediate ends up outside the ring, and the attack is called endoif it ends up inside the newly formed ring.

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Cyclization is extremely rapid and exo selective.Hence, in many cases, exo cyclization is favored over endo cyclization.

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The more stable free radical is the one which is more substituted.