Tutorial 3 - Chemistry 2OA3 Oct.25 to Nov 5th 2010 Tutorial...

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Chemistry 2OA3 Oct.25 to Nov 5th, 2010 Tutorial 3 1. An unknown compound absorbs in the IR just below 3000 cm -1 , but there are no other absorbances except in the fingerprint region. The molecular formula is C 6 H 14 O. i) How many double bonds or rings does the molecule contain? In the proton NMR spectrum, there is a series of 7 lines (a septuplet) centered at chemical shift 3.7, which integrates for two protons. Also, there is a doublet at shift 1.1, which integrates for 12 protons. No other NMR signals are present. In the carbon-13 NMR, there are only 2 lines, at δ 20 and 70; DEPT NMR shows that these are CH and CH 3 type carbons, respectively. ii) Sketch the proton NMR spectrum. 3.7 1.1 ppm Integration iii) What do the shifts tell you? Where is the heteroatom(s) located based on the observed chemical shifts? iv) What do the multiplicities of the peaks in the proton NMR reveal? Suggest a partial structure for the molecule, based on the coupling.
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