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problemset1 - Massachusetts Institute of Technology Organic...

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Massachusetts Institute of Technology Organic Chemistry 5.13 September 10, 2003 Prof. Timothy F. Jamison Problem Set #1 Organic Structure Determination DUE DATE: Thursday, September 18, 2003 at 12 noon NOTE: If mass spectrometry (MS) data are provided, the highest molecular ion given corresponds to the molecular ion (M + ), unless otherwise noted. 1. In class we derived a formula for calculating the “index of hydrogen deficiency,” which is equal to the sum of the number of rings and π-bonds in an organic molecule. We showed that number of atoms of each element is multiplied by a factor (hereafter called “deficiency factor”) in this equation (C: 1, H: –1/2, O: 0, etc.). a. Derive the deficiency factor for phosphorus (P), using triphenylphosphine (C 6 H 5 ) 3 P, a common laboratory reagent (e.g. Wittig reactions), as the basis for your calculations. b. Derive the deficiency factor for phosphorus (P), using triphenylphosphine oxide (C 6 H 5 ) 3 P=O (a byproduct in the Wittig reaction), as the basis for your calculations.
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