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Please help in analyzing this unknown compound and include methods/reasoning use

ID: 947872 • Letter: P

Question

Please help in analyzing this unknown compound and include methods/reasoning used to justify identification utilizing included data. Also Identify the "Named Reaction" represented and the significance. Thank you for your help!  

Note: FT-IR as Solid, 1H-NMR and 13C-NMR (solution using dueterated chloroform as solvent, relative integration values included next to peaks)

Experimental melting Point: 134.0-135.5 Celcius

Solubility: insoluable in water, Soluable in dueterated chloroform used as NMR solvent

Physical Observations: fine powder white in color, fruity scent

(Synthesis Method Given) NH 1. NaNO2, HCl, H.O 2. H2O , Acetonitrile, CuCl2 OH

Explanation / Answer

Compound formed is cinnamic acid. Name reaction is Heck reaction. In the above reaction copper chloride acted as a catalyst for the formation of product.

In IR spectrum 1671cm-1 is the peak for carbonyl of acid group in cinnamic acid that is formed.

In H1 NMR data there are 3 peaks in aromatic region corresponding to 5 protons of aromatic ring. (2 equivalent protons at 7.81, 2equivant protons at 7.55 and one proton at 7.40). Proton at 6.47 shows doublet corresponds to proton alpha to acid group. and proton at 0.0087 corresponds to benzylic proton.

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