Designing organic syntheses by Stuart Warren

By Stuart Warren

Teaches scholars to take advantage of the language of sythesis without delay (utilizing the grammar of synthon and disconnection) instead of translating it into that of natural chemistry.

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Structure 97 has a stable (singlet) resonance structure that has no radical character, so it exhibits predominantly singlet character. Structure 98 cannot generate a Kekule resonance structure (that is, a structure having only double and single bonds) that does not have radical character. Thus it is a triplet species because triplet diradicals typically are lower in energy than are singlet diradicals (see Chapter 12). Solutions Manual for Perspectives on Structure and Mechanism in Organic Chemistry, Second Edition.

47 48 SOLUTIONS MANUAL F OR PE RSPECTIVE S O N STRUCTURE AND M ECHANISM b. F 1 values are closely related to P12 values, which increase as each additional double bond is added to the allyl system. In essence, the F 1 value of a polyenyl system decreases with increasing chain length because the unpaired electron density is distributed over a larger molecule, meaning that the overlap of the two terminal p centers is more like that in a polyene. In polyenes F 1 values decrease with increasing chain length because P12 values decrease (and P23 values increase) with increasing chain length.

D. ; Perelman, M. J. Am. Chem. Soc. 1958, 80, 1430; Brown, H. ; Berneis, H. L. J. Am. Chem. Soc. , W. ; Cockerill, A. F. Mechanisms of Elimination Reactions; Wiley-Interscience: New York, 1973; p. 173. 8 kcal/mol 3 CO NF OR MA TI ON AL AN AL Y S I S A ND MO L E CU L A R MEC HA NI CS 2,4,4-Trimethyl-1-pentene is less substituted. However, 2,4,4trimethyl-2-pentene has a t-butyl group that is cis to a methyl group, which raises the energy of the compound due to van der Waals repulsion. The experimental data were reported by, and some discussion given by, Turner, R.

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