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Organic Chemistry
Found in: Page 128

Short Answer

Question: Although penicillin G has two amide functional groups, one is much more reactive than the other. Which amide is more reactive and why?


The amide group that forms the four-membered ring is more reactive due to the ring strain.

See the step by step solution

Step by Step Solution

Step 1: Amide

Organic functional groups that consist of a carboxyl group bonded to an amine group are termed amides.

The general formula of an amide is , where R, , and R2 are hydrogen atoms or hydrocarbons.

Step 2: Amide groups in penicillin G

Penicillin G contains two amide groups.

These are represented in the figure given below.

Amide groups in penicillin G

Step 3: The most reactive amide in penicillin G

Ring structures (generally the rings involving three or four carbon atoms) develop a strain as their bond angles are less than the expected angle.

The strained rings are generally unstable or more reactive, and try to attain more stability by relieving the strain.

In the case of penicillin G, the amide group that exists as a ring is more reactive than the other as it tries to relieve its strain to attain stability.

Most reactive amide in penicillin G

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