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. c. Why are the two factors derived different? In other words, what do you need to know about each element in a particular organic molecule? Based on these considerations, write a general
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This note was uploaded on 11/27/2011 for the course CHEMICAL E 20.410j taught by Professor Rogerd.kamm during the Spring '03 term at MIT.

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problemset1 - Massachusetts Institute of Technology Organic...

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