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Enantiomers and Chiral Molecules Enantiomers always have the possibility of existing in pairs.

We may not always find that nature (or a reaction) has produced a pair of enantiomers, however. In fact , in nature we often find only one enantiomer of the two that are possible. We shall find ou t later why this is often the case. Typically, when we carry out a chemical reaction, we fin d that the reaction produces a pair of enantiomers. Again, we will explain later why this o ccurs. What structural feature must be present for two molecules to exist as enantiomer s Enantiomers occur only with compounds whose molecules are chiral. How do we recognize a chiral molecule A chiral molecule is one that is not superposable on its mirror image. What is the relationship between a chiral molecule and its mirror image The relationship is one that is enantiomeric. A chiral molecule and its mirror image are said to be enantiomers of each other. Review Problem 5.1 Classify each of the following objects as to whether it is ch iral or achiral (a) A screwdriver (b) A baseball bat (c) A golf club (d) A tennis shoe (e) An ear (f) A woodscrew (g) A car (h) A hammer The chirality of molecules can be demonstrated with relatively simple compounds. Consider, for example, 2-butanol Until now, we have presented the formula for 2-butanol as though it represented only one compound and we have not mentioned that molecules of 2-butanol are chiral. Becau se they are, there are actually two different 2-butanols and these two 2-butanols are en antiomers. We can understand this if we examine the drawings and models in Fig. 5.3. If model I is held before a mirror, model II is seen in the mirror and vice vers a. Models I and II are not superposable on each other; therefore, they represent different , but isomeric, molecules. Because models I and II are nonsuperposable mirror images of each oth er, the molecules that they represent are enantiomers. 2-Butanol OH (b) I II OH H CH3 CH3 CH2 CH3 H HO CH3 CH2 (c) CH3 HO H CH3

CH2 H OH CH3 CH3 CH2 II I Figure 5.3 (a) Three-dimensional drawings of the 2-butanol enantiomers I and II. (b) Models of the 2-butanol enantiomers. (c) An unsuccessful attempt to superpose models of I and II. I II H OH HO H (a) Construct handheld models of the 2-butanols represented in Fig. 5.3 and demonstr ate for yourself that they are not mutually superposable. (a) Make similar models of 2-b romopropane. Are they superposable (b) Is a molecule of 2-bromopropane chiral (c) Would you expect to find enantiomeric forms of 2-bromopropane