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Additional problems before the quiz

Additional problems before the quiz - Additional problems...

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Additional problems before the quiz: The quiz on Wed will consist of 4 questions, 2 spectral, one synthesis, one synthesis combined with NMR. Let’s take problem #3 Homework #3 Starting with methylbenzene and using any monofunctional precursors with 3 or fewer carbons and any reagents that you need to give the product of which the NMR spectrum is given below. C 16 H 16 O IR 1750cm -1 0 1 2 3 4 5 6 7 8 PPM 10H 2H 4H Step 1: 5 unsaturation units Step 2: look in the NMR aromatic region (10H-two benzene rings mono substituted) look at IR C=O that will be all unsaturated units. Subtract from MF C 16 H 16 O- C 11 H 10 O (2 phenyl and 1 C=O) you are left with C 3 H 6 (three CH 2 ) Step 3: address the proton spectrum, singlet at 3.5 corresponding to CH 2 (attached to a carbons with no H), triplet at 2.75 corresponding to two CH 2 , the triplet splitting indicates attachment to CH 2 , the two CH 2 happened to come at the same chemical shift. Now put all these information together: O Now how are you going to synthesize this ketone???
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