How to Carry out a Multistep Synthesis – Part 5

Multistep synthesis is the artificial execution of multiple organic chemical reactions to obtain one or more products by physical and chemical manipulations.


Retrosynthetic analysis is a problem-solving approach in the organic syntheses, achieved by transforming a target molecule into simpler precursor structures regardless of any potential reactivity/interaction with reagents, and repeated until a simple or commercially available structure is reached, which can be used as a starting material to synthesize the target molecule.

Polyvinyl acetate (PVA or PVAc), a rubbery synthetic thermoplastic polymer, which is commonly referred to as PVA glue, wood glue, white glue, carpenter's glue, school glue, or Elmer's Glue, is a widely available adhesive used for porous materials like wood, paper, and cloth.

Question:

Propose a synthesis of PVA by using any starting material with a maximum of two carbons and its derivatives BUT a reactant/reagent molecule that adds any carbon atom to the final product. Think about commercially viable compounds, processes and green chemistry.

Solution infographic:




Click/tap here to enlarge the image

Ox = Oxidation, AWS = Aldehyde water shift, AE = Electrophilic addition

Let's keep in mind that any multistep synthesis is possible via several routes ❗Questions ❓ Let Chemaficionado know in the comments below or at mychemistryhomework@gmail.com❗

References:

(1)    Wikipedia Contributors. Chemical synthesis. Wikipedia. https://en.wikipedia.org/wiki/Chemical_synthesis.

‌(2)    Retrosynthetic analysis. Wikipedia. https://en.wikipedia.org/wiki/Retrosynthetic_analysis.

(3)    Brown, C.; Ford, M. Higher Level Chemistry, 2nd ed.; Pearson Education: Harlow, Essex, 2014.

(4)    Ncert. Chemistry : Textbook for Class XI - Part.II; National Council Of Educational Research And Training: New Delhi.

(5)    Graham, T. W.; Fryhle, C. B.; Snyder, S. A. Organic Chemistry.; Hoboken, Nj John Wiley Et Sons, Inc, 2016.

(6)    Wikipedia Contributors. Polyvinyl acetate. Wikipedia. https://en.wikipedia.org/wiki/Polyvinyl_acetate.

(7)    Vinyl acetate. Wikipedia. https://en.wikipedia.org/wiki/Vinyl_acetate.

(8)    Wikipedia. Acetic acid. Wikipedia. https://en.wikipedia.org/wiki/Acetic_acid.

(9)    Wikipedia Contributors. Ethanol. Wikipedia. https://en.wikipedia.org/wiki/Ethanol.

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