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Spectroscopy Learning Module, Part 4

Spectroscopy Learning Module, Part 4 - Think of a problem...

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Think of a problem as a puzzle, and approach it with logic Calculate the degrees of unsaturation first Deg. Unsat = [2*C – H – hal + N +2]/2 Look at IR for functional groups L k t t NMR f i f ti b t Look at proton NMR for information about neighboring groups Put pieces together to arrive at solution Check to make sure your structure agrees with your spectra 1
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C 6 H 10 O 3 2
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Calculate degrees of unsaturation first Deg. Unsat = [2*C – H – hal + N +2]/2 So for the formula in this problem, C 6 H 10 O 3 , the degree of unsaturation is (2*6 10 0+0+2)/2 which degree of unsaturation is (2*6-10-0+0+2)/2, which comes out to be 2 degrees of unsaturation. Recall that a π bond or a ring count as a degree of unsaturation. So, we must have… T d bl b d Two double bonds, or One double bond and one ring, or Two rings, or One triple bond 3
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In the IR, we see signals for the C-H stretching In the IR, we see signals for the C H stretching and for C=O stretching Note there is no indication of a hydroxyl C-H stretching C=O stretching 4
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