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A Mnemonic for the Inositols

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Terence J. Painter

University of Trondheim, Norway

J. Chem. Educ., 1996, 73 (10), p 949

DOI: 10.1021/ed073p949

Publication Date (Web): October 1, 1996

Abstract

The mnemonic derives from the mythical tale of Scylla and Charybdis in Homer's Odyssey (chapter 12). It takes the form of an imaginary headline in a newspaper: SCYLLA MEETS CHARYBDIS - EPIC NEWS MUCH ALARMS SICILY. The first two or three letters in each of these eight words remind the user that the nine configurational prefixes are scyllo-, meso-, (or myo-), chiro- [(+) and (-)], epi-, neo-, muco-, allo-, and cis-, respectively. The mnemonic also arranges the prefixes in an order that allows the configurations to be derived in a logical manner by performing a defined sequence of imaginary configurational inversions (epimerizations) around a cyclohexane ring. The all-equatorial, chair conformation of scyllo-inositol is selected as the starting point, and the sequence of inversions is defined by a systematic permutation of possibilities for performing one, two or three inversions in succession (1; 1 and 2; 1 and 3; 1 and 4; 1, 2 and 3; 1, 2 and 4; and finally 1, 3 and 5). In the case of the two chiro-inositols, the enantiomeric form is determined simply by the direction (clockwise or counterclockwise) around the ring in which the imaginary inversions are performed. This also applies formally to allo-inositol, but in that case the two optical enantiomers are isoenergetic chair conformers in rapid equilibrium.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Organic Chemistry

Keywords (Pedagogy):

Humor / Puzzles / Games

Keywords (Subject):

Alcohols

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This article has been cited by 1 ACS Journal articles (1 most recent appear below).

A Simple Mnemonic for Tautomerization Mechanisms in Organic Chemistry
Chad E. Stephens
Journal of Chemical Education2010 87 (11), 1186-1187
- A Simple Mnemonic for Tautomerization Mechanisms in Organic Chemistry
  Chad E. Stephens
  Journal of Chemical Education2010 87 (11), 1186-1187
  The familiar word OREO (as in the cookie) is presented as a simple mnemonic for remembering the basic steps of the classical tautomerization mechanisms in organic chemistry. For acid-catalyzed tautomerizations, OREO stands for proton on, resonance, proton ...
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