GOLCONDANE, molecule named after Golconda fort, Hyderabad

A  cage hydrocarbon was called Golcondane by the first people to synthesis it in 1993, Mehta and Reddy, in honour of the 400th anniversary of the founding of the Indian city of Hyderabad, whose ancient name was Golconda.

The interesting cage compound “Golcondane” (C20H24) has recently been synthesized, more or less according to the route shown here. (In the actual case, there were carbonyl groups that had to be reduced at the end of the synthesis.) Do MMX calculations on golcondane, on the three precursors, and on its decomposition product; discuss the relative stability of these compounds and identify the source(s) of their strain energy. [The origin of the name “golcondane” is so obscure that the interested reader should consult the cited reference.

A. Nickon and E.F. Silversmith, ‘Organic Chemistry: The Name Game‘, Pergamon, 1987; P. von R. Schleyer, E., and M.G.B. Drew. J. Am. Chem. Soc. 90, (1968) 5034.

“Golcondane: A Novel, Caged, Nonacyclic C20H24‐Hydrocarbon of D2d Symmetry”.G. Mehta and S.H.K. Reddy, Angew. Chem., Int. Ed. Engl. 32, (1993) 1160.  http://onlinelibrary.wiley.com/doi/10.1002/anie.199311601/abstract

Golconda Fort!! hyderabad India

The Beautiful Golconda Fort ,Hyderabad
The Beautiful Golconda Fort ,Hyderabad india
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Branched Enynenynols

“Old MacDonald Named a Compound: Branched Enynenynols”

that was originally published in the J. Chem. Ed. 74 (1997) 782, about what would happen if ‘Old MacDonald’ were a chemist, and made molecules that have the shapes of animals. Some are shown below.

http://pubs.acs.org/doi/abs/10.1021/ed074p782

Department of Chemistry, Hofstra University, Hempstead, NY 11590
J. Chem. Educ., 1997, 74 (7), p 782
DOI: 10.1021/ed074p782
Publication Date (Web): July 1, 1997