Chemistry
Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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Stereochemistry and Isomerism
Stereochemistry deals with the three-dimensional structure and properties of molecules. It explains the arrangement of atoms and their manipulation within a molecule in a 3D structure. Stereochemistry can be dealt with all types of molecules. Based on th…
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9L.4

Learning Goal: To identify chiral molecules, understand optical isomerism, and draw enantiomers. Optical isomers, or enantiomers, are nonsuperimposable mirror images of each other. For example, 2-chlorobutane and its mirror image (Figure 1 ) are optical isomers. Gloves are an example of common objects with this property. Right and left gloves are mirror images, but a right-handed glove does not fit on your left hand, and vice versa. In contrast, the letter "A" is an example of an object that is identical to its mirror image. Figure Properties of optical isomers Optical isomers generally have the same properties, differing only in their chemical behavior in a chiral environment (for example, with enzymes) and in the direction in which they rotate plane-polarized light. The / (levorotatory) isomer of an enantiomer pair rotates polarized light in a counterclockwise direction, whereas the d (dextrorotatory) isomer rotates polarized light the same amount, but in a clockwise direction. A racemic mixture is a mixture with equal amounts of the I and d isomers. Part B You have a racemic mixture of d-2-butanol and /-2-butanol. The d isomer rotates polarized light by +13.5°. What is the rotation of the polarization of light of your mixture? Express your answer in degrees. ► View Available Hint(s) VE ΑΣΦ Submit Part C Two products, structural isomers of each other, are possible for the bromination of butane via the reaction CH3CH₂CH₂CH3 + Br₂ ? heat or light One of these products exhibits optical isomerism. Draw this product. Assume mono substitution. Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. ► View Available Hint(s)
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Transcribed Image Text:Learning Goal: To identify chiral molecules, understand optical isomerism, and draw enantiomers. Optical isomers, or enantiomers, are nonsuperimposable mirror images of each other. For example, 2-chlorobutane and its mirror image (Figure 1 ) are optical isomers. Gloves are an example of common objects with this property. Right and left gloves are mirror images, but a right-handed glove does not fit on your left hand, and vice versa. In contrast, the letter "A" is an example of an object that is identical to its mirror image. Figure Properties of optical isomers Optical isomers generally have the same properties, differing only in their chemical behavior in a chiral environment (for example, with enzymes) and in the direction in which they rotate plane-polarized light. The / (levorotatory) isomer of an enantiomer pair rotates polarized light in a counterclockwise direction, whereas the d (dextrorotatory) isomer rotates polarized light the same amount, but in a clockwise direction. A racemic mixture is a mixture with equal amounts of the I and d isomers. Part B You have a racemic mixture of d-2-butanol and /-2-butanol. The d isomer rotates polarized light by +13.5°. What is the rotation of the polarization of light of your mixture? Express your answer in degrees. ► View Available Hint(s) VE ΑΣΦ Submit Part C Two products, structural isomers of each other, are possible for the bromination of butane via the reaction CH3CH₂CH₂CH3 + Br₂ ? heat or light One of these products exhibits optical isomerism. Draw this product. Assume mono substitution. Draw the molecule on the canvas by choosing buttons from the Tools (for bonds), Atoms, and Advanced Template toolbars. The single bond is active by default. ► View Available Hint(s)
Figure Cl Jadian CH H₂C H*** CH₂CH3 H3CH₂C 2-Chlorobutane < Cl 1 of 1 CH3
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Transcribed Image Text:Figure Cl Jadian CH H₂C H*** CH₂CH3 H3CH₂C 2-Chlorobutane < Cl 1 of 1 CH3
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Step 1: Polarisation of light
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Step 2: Rotation of Polarisation of light
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Step 3: Bromination of butane
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