Question

"Super glue" contains methyl cyanoacrylate, C=C(C)C(=O)OC which readily polymerizes upon exposure to traces of water or alcohols on the surfaces to be bonded together. The polymer provides a strong bond between the two surfaces. Draw the structure of the polymer formed by methyl cyanoacrylate.

Short answer

The structure of the polymer formed by methyl cyanoacrylate is represented as: \[ [CH_3—C(=O)—OCH_3—C—(N—C(=O)—OCH_3—)]_n \] where "n" indicates the number of repeating units in the polymer. This polymerization occurs through anionic polymerization at the nitrile group and the carbonyl group and is facilitated by traces of water or alcohol.

Step-by-step solution

Draw the structure of methyl cyanoacrylate from the SMILES notation

The SMILES notation represents the structure of a molecule: "C=C(C)C(=O)OC" Let's interpret this notation to obtain the structure of methyl cyanoacrylate: - The double bond between two carbon atoms is represented by C=C. - Then the first carbon has a methyl group, indicated by (C). - The second carbon is attached to a carbonyl group and a methoxy group, represented by C(=O) and OC, respectively. The structure of the methyl cyanoacrylate molecule is shown below: CH₃—C≡N—C(=O)—OCH₃

Identify the reactive sites of the monomer

Next, we need to identify the reactive sites of the monomer, where the polymerization will take place. The polymerization of methyl cyanoacrylate occurs through anionic polymerization at the nitrile group and the carbonyl group, as these contain highly reactive and polar functional groups. The reactive site in methyl cyanoacrylate, which initiates the polymerization, is the carbon-nitrogen triple bond.

Draw the structure of the polymer

Now that we have identified the reactive sites in the monomer, let's draw the polymer form of methyl cyanoacrylate. During the polymerization, the Nitrile group (-C≡N) opens up, and the monomers link with each other in a linear chain. The process repeats multiple times to form a long chain, creating the desired polymer. The structure of the polymer formed by methyl cyanoacrylate is shown below: [CH₃—C(=O)—OCH₃—C—(N—C(=O)—OCH₃—)]_n Here, "n" indicates the number of repeating units in the polymer. This structure represents the polymer bonded at the carbon and nitrogen atoms, with traces of water or alcohol facilitating the process.