Organic Synthesis- Final Year Project 2023

By atikanisaaziz991 | Updated: March 14, 2025, 8:40 p.m.

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Title: Silver Catalysed Free Radical Alkylation of Methyl Naphthoquinone

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Prepared by:
Tengku Atika Nisa binti Tengku Aziz
Bachelor of Chemistry (Hons.) Forensic Analysis
Silver Catalysed Free Radical Alkylation of Methyl Naphthoquinone
Problem statement
Cancer is the second leading cause of death in the world.

Alkyl naphthoquinone derivatives from natural compound are not easily isolate.

As compounds origin from natural resources, making it not easily available in large amount.

Significant of study
Provides more knowledge on chemical reaction and reactivity of naphthoquinone.

Finding more effective and alternative pathways in synthesizing alkyl naphthoquinone derivatives.

Provide alternative drugs for treatment such as cancer and antifungal.

Objective of study
To synthesize an alkyl substituted naphthoquinone derivatives.

To develop efficient method for synthesizing the naphthoquinone derivatives.

To identify isolated  product with spectroscopic technique.

Heating all the starting materials together with silver nitrate at 80℃. Potassium peroxydisulfate in distilled water was added dropwise in the mixture.
Step 1
Step 2
The progress of the reaction was monitored by TLC every 1 hour.
Methodology
The product was extracted with DCM and distilled water and evaporated using rotary evaporator.
Step 3
Step 4
The products were isolated and separated using a short column chromatography.
Step 5
Further evaporated using high vacuum for 8 hoursto get rid all the volatile substances in the product.
Results
Reaction 1: Mechanism
Reaction 1: IR Result
Reaction 1: H NMR Result
Reaction 1: C NMR Result
Reaction 2: Mechanism
Reaction 2: IR Result
Reaction 2: H NMR Result
Reaction 2: C NMR Result
Reaction 3: Mechanism
Reaction 3: IR Result
Reaction 3: H NMR Result
Reaction 3: C NMR Result
Conclusion
The reaction between menadione 45 and hexanoic acid 46 has successfully gave compound 49 with 29.93% of yield.

The second reaction involving menadione 45 and glutaric acid 47 also has successfully gave compound 50 with 18.96% yield.

The third reaction of menadione 45 and lauric acid 48 gave compound 51 with 35.72% of yield.

All these compounds has been proven by 1H NMR, 13C NMR and IR

Recommendation
Modification of solvent system different type of solvent should be employed to increase the yield.

To improve the yield of the product, it is recommended to carry out the reaction at higher temperature with slightly higher concentration of potassium persulfate.

Modification of catalyst also can be further study such as employing organocatalyst.

THANK YOU

Organic Synthesis- Final Year Project 2023

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