Tutorial 3 answers - Chemistry 2OA3 Oct. 16, 2010 Tutorial...

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Chemistry 2OA3 Oct. 16, 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? 0 using IHD: [(#C*2)+2]- #H –X + N = (6*2)+2-14 = 0 (you ignore oxygens in the formula) 2 2 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 3 and CH type carbons, respectively. ii) Sketch the proton NMR spectrum. 3.7 1.1 ppm Integration 1 6 iii) What do the shifts tell you? What heteroatom(s) is/are present, in order to account for the shifts? The 2H signal is shifted by an electronegative atom, e.g. Cl, O, N etc. (O in this case)
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This note was uploaded on 05/16/2011 for the course CHEM BIO 20a3 taught by Professor Stover during the Fall '10 term at McMaster University.

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Tutorial 3 answers - Chemistry 2OA3 Oct. 16, 2010 Tutorial...

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