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A student carried out the following synthetic scheme. H3C -CH3 -CH3 condition 1 H3C O SOCI Compound Q -CH3 -OH Compound R H3C H3C

 

A student carried out the following synthetic scheme. H3C -CH3 -CH3 condition 1 H3C O SOCI Compound Q -CH3 -OH Compound R H3C H3C Compound P Compound S H/Pt Answer the following: 1. List all the IR bond vibrations expected in the diagnostic region of the IR spectrum of Compound R and S. Comment on the change expected in the C=O vibration and briefly give a reason for the change. 2. Write down the reagents for reaction condition 1 3. Predict the H NMR spectral data Compound S. You may label the hydrogens in different environments and then indicate their expected chemical shift range and the multiplicity. Label Chemical shifit (ppm) Multiplicity Comments on shielding/deshielding effects

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