Massachusetts Institute of Technology Organic Chemistry 5.13 Prof. Timothy F. Jamison Problem Set #1 This problem set is worth 50/8 = 6.25 points toward your final grade; each problem is worth 1.25 points. NOTE: If mass spectrometry (MS) data are provided, the highest molecular ion given corresponds to the molecular ion (M + ), unless otherwise noted. 1. Derive an expression for the largest possible IHD for a neutral (no overall charge; zwitterions ok), stable compound having n carbon atoms and zero or more H, N, and O atoms (e.g., CH 4 O). For the purposes of this problem, “stable” is defined as a structure whose atoms all form the “standard” number of bonds. That is, all of the C atoms have 4 bonds, all the H (if any) have 1, all the N (if any) have, and all the O (if any) have 2. Express your answer as function of n , and illustrate with two specific structures. Calculate and provide the numerical value of the IHD for your examples. 2.
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