Whether monochlorination or monobromination of 2,3-Dimethylbutane would be synthetically useful procedure or not should be determined. Concept introduction: The monobromination or monochlorination performed with ultraviolet light proceeds via radical chain mechanism. In the halogenation reaction, the reactivity of tertiary C-H bond is higher than that of secondary which is further higher than primary C-H bonds. This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.In case of tertiary radical, the maximum amount of hyperconjugation can occur because of nine adjacent C – H bonds. Thus the extent of delocalization is greatest in tertiary; thus tertiary radicals have more tendencies to form. In primary number of immediate adjacent hydrogen left after C – H bond cleavage is only two and least hyperconjugation makes it least reactive.

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Chapter 3.9, Problem 3.11TIY

Interpretation Introduction

Interpretation:Whether monochlorination or monobromination of 2,3-Dimethylbutane would be synthetically useful procedure or not should be determined.

Concept introduction: The monobromination or monochlorination performed with ultraviolet light proceeds via radical chain mechanism.

In the halogenation reaction, the reactivity of tertiary C-H bond is higher than that of secondary which is further higher than primary C-H bonds.

This can be attributed to stability of radical formed upon C – H bond cleavage via hyperconjugation.In case of tertiary radical, the maximum amount of hyperconjugation can occur because of nine adjacent C – H bonds. Thus the extent of delocalization is greatest in tertiary; thus tertiary radicals have more tendencies to form. In primary number of immediate adjacent hydrogen left after C – H bond cleavage is only two and least hyperconjugation makes it least reactive.

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