Question 4.59: Within experimental error, the steric strain caused by a bro......

Organic Chemistry Study Guide: Key Concepts, Problems, and Solutions [1424398]

Within experimental error, the steric strain caused by a bromine atom is the same as that of a chlorine atom. Taking into account the “size” of the atoms and the length of the carbon–halogen bond, explain these data.

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The C—Br bond is longer than the C—Cl bond, so the distance separating the bromine atom from the C-3 and C-5 hydrogen atoms is larger. In addition, the bromine atom is more polarizable than the chlorine atom, and its electrons may be more easily distorted away from the steric congestion in the axial conformation.

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