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A C-D (carbon-deuterium) bond is harder to break than a C-H bond, and, consequently, reactions in...

A C-D (carbon-deuterium) bond is harder to break than a C-H bond, and, consequently, reactions in which C-D bonds are broken proceed more slowly than reactions in which C-H bonds are broken. What mechanistic information comes from the observation that perdeuterated benzene, C6D6, is nitrated at the SAME rate as normal benzene, C6H6 (k1=k2)? HINT: write the mechanism for the nitration of benzene.

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Answer #1

The mechanism for the nitration of benzene is as shown.

Since, perdeuterated benzene, C6D6, is nitrated at the SAME rate as normal benzene, C6H6 (k1=k2), the C-D bond is not broken in the rate determining step. The rate determining step is the attack of pi elecrons of benzene to the nitronium ion.

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