Question

A covalent bond in tert-butyl bromide breaks in a suitable polar solvent to give ions.

1. Name the anion produced by this breaking of a covalent bond.
2. Indicate the type of bond breaking in this case.
3. Comment on the geometry of the cation formed by such bond cleavage.

Answer 1

1. \[\begin{array}{cc}
   \ce{CH3}\phantom{..............}\ce{CH3}\phantom{.........}\\
   |\phantom{..................}|\phantom{............}\\
   \ce{H3C - C - Br} \ce{->[aq]} \ce{H3C - C^\oplus} + \ce{\underset{Bromide ion (anion)}{Br-}}\\
   |\phantom{..................}|\phantom{............}\\
   \ce{CH3}\phantom{..........}\ce{\underset{tert-butyl Cation}{CH3}}\phantom{.....}\\
   \end{array}\]
2. Heterolytic cleavage/fission takes place as charged ions are produced.
3. tert-Butyl carbocation formed in the given cleavage has trigonal planar geometry.