How to Carry out a Multistep Synthesis – Part 1

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.

Glycerol finds its applications in food/medical/entertainment industry, botanical extracts, electronic cigarette liquid, vibration damping, or as an antifreeze/ultrasonic couplant/internal combustion fuel, or a chemical intermediate.

Question:

How would you do the following transformation?



Click/tap here to enlarge the image

Solution infographic:



Click/tap here to enlarge the image

AE = Electrophilic addition, SN2 = Nucleophilic substitution bimolecular, NBS = N-Bromosuccinimide

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❗

NOTE: Post updated since published

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)    Wikipedia Contributors. Radical substitution. Wikipedia.

(‌4)    Wikipedia Contributors. Wohl–Ziegler bromination. Wikipedia. https://en.wikipedia.org/wiki/Wohl%E2%80%93Ziegler_bromination.

‌(5)    Wikipedia Contributors. N-Bromosuccinimide. Wikipedia. https://en.wikipedia.org/wiki/N-Bromosuccinimide.

‌(6)    Wikipedia Contributors. Electrophilic addition. Wikipedia. https://en.wikipedia.org/wiki/Electrophilic_addition.

‌(7)    Wikipedia Contributors. Markovnikov’s rule. Wikipedia. https://en.wikipedia.org/wiki/Markovnikov%27s_rule.

(‌8)    Wikipedia Contributors. Nucleophilic substitution. Wikipedia. https://en.wikipedia.org/wiki/Nucleophilic_substitution.‌

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

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