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General Chemistry Principles, Patterns, and Applications, 2011

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e superimposed by simple rotation. Thus the carbon is no longer a chiral center. Asymmetric carbon<br />

atoms are found in many naturally occurring molecules, such as lactic acid, which is present in milk <strong>and</strong><br />

muscles, <strong>and</strong> nicotine, a component of tobacco. A molecule <strong>and</strong> its nonsuperimposable mirror image are<br />

calledenantiomers (from the Greek enantiou, meaning “opposite”).<br />

Figure 24.7 Comparison of Chiral <strong>and</strong> Achiral Molecules<br />

(a)<br />

Bromochlorofluoromethane is a chiral molecule whose stereocenter is designated with an asterisk.<br />

Rotation of its mirror image does not generate the original structure. To superimpose the mirror<br />

images, bonds must be broken <strong>and</strong> reformed. (b) In contrast, dichlorofluoromethane <strong>and</strong> its mirror<br />

image can be rotated so they are superimposable.<br />

Saylor URL: http://www.saylor.org/books<br />

Saylor.org<br />

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