Problem: Two molecules used in the polymer industry are azodicarbonamide and methyl cyanoacrylate. Their structures areAzodicarbonamide is used in forming polystyrene. When added to the molten plastic, it decomposes to nitrogen, carbon monoxide, and ammonia gases, which are captured as bubbles in the molten polymer. Methyl cyanoacrylate is  super glue. As the glue sets, methyl cyanoacrylate polymerizes across the carbon–carbon double bond. b. Which hybrid orbitals are used by the carbon atoms in each molecule and the nitrogen atom in azodicarbonamide?

🤓 Based on our data, we think this question is relevant for Professor Albright's class at UMICH.

FREE Expert Solution

Orbitals that can be used by the central atom:


Subshell                   Total # of orbitals 

        s           _                1 orbital  

        p          _ _ _            3 orbitals

        d        _ _ _ _ _        5 orbitals



Hybrid orbitals for each carbon atom in azodicarbonamide is sp2

  • C at b and d: 3 electron groups (3 orbitals)
    • p p = sp2
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Problem Details

Two molecules used in the polymer industry are azodicarbonamide and methyl cyanoacrylate. Their structures are


Azodicarbonamide is used in forming polystyrene. When added to the molten plastic, it decomposes to nitrogen, carbon monoxide, and ammonia gases, which are captured as bubbles in the molten polymer. Methyl cyanoacrylate is  super glue. As the glue sets, methyl cyanoacrylate polymerizes across the carbon–carbon double bond. 

b. Which hybrid orbitals are used by the carbon atoms in each molecule and the nitrogen atom in azodicarbonamide?

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Our tutors have indicated that to solve this problem you will need to apply the Hybridization concept. You can view video lessons to learn Hybridization. Or if you need more Hybridization practice, you can also practice Hybridization practice problems.

What professor is this problem relevant for?

Based on our data, we think this problem is relevant for Professor Albright's class at UMICH.

What textbook is this problem found in?

Our data indicates that this problem or a close variation was asked in Chemistry: An Atoms First Approach - Zumdahl 2nd Edition. You can also practice Chemistry: An Atoms First Approach - Zumdahl 2nd Edition practice problems.