Wedge-shaped bond dashed

A note on good practice Dashed and solid wedge-shaped bonds are commonly used when displaying organic structures to convey a sense of the three-dimensional shapes. The dashed wedge-shaped bonds go into the page and the solid wedge-shaped bonds come toward us. The thin lines are in the plane of the paper. 

FIGURE 3-3 Stereoisomerism in n-amino acids, (a) The two stereoisomers of alanine, l- and o-alanine, are nonsuperimposable mirror images of each other (enantiomers), (b, c) Two different conventions for showing the configurations in space of stereoisomers. In perspective formulas (b) the solid wedge-shaped bonds project out of the plane of the paper, the dashed bonds behind it. In projection formulas (c) the horizontal bonds are assumed to project out of the plane of the paper, the vertical bonds behind. However, projection formulas are often used casually and are not always intended to portray a specific stereochemical configuration. 

FIGURE 7-2 Three ways to represent the two stereoisomers of glyc-eraldehyde. The stereoisomers are mirror images of each other. Ball-and-stick models show the actual configuration of molecules. By convention, in Fischer projection formulas, horizontal bonds project out of the plane of the paper, toward the reader vertical bonds project behind the plane of the paper, away from the reader. Recall (see Fig. 1-17) that in perspective formulas, solid wedge-shaped bonds point toward the reader, dashed wedges point away. 

Fig. 7.29 The enantiomers of a-hexachlorocyclohexane (a-HCH). Bold wedge shaped bonds represent bonds rising from the plane of the page toward the viewer, and bonds represented by dashed lines are receding from the plane of the page away from the viewer. See also Box 7.3.

Use heavy and dashed wedged lines to show the shapes of the following molecules. Show the bond dipole of each polar bond and show the overall dipole of each molecule. 

The three-dimensional structure of ethane, C2H6, has the shape of two tetrahedra joined together. Each carbon atom is sp3 hybridized, with four sigma bonds formed by the four sp3 hybrid orbitals. Dashed lines represent bonds that go away from the viewer, wedges represent bonds that come out toward the viewer, and other bond lines are in the plane of the page. All the bond angles are close to 109.5°. 

Figure 5. CH2 vibrational modes. Small circles represent hydrogen, and large circles represent carbon. Wedge-shaped heavy lines represent the bond in front of the plane of the page, and wedge-shaped dashed lines represent the bond behind the plane of the page.

The three molecules of interest are methane (4A), ammonia (6A), and water (7A), shown first in the Lewis electron dot representations. Using the VSEPR model, these three molecules are drawn again using the wedge-dashed line notation. Methane (CH4, 4B) has no unshared electrons on carbon but there are electrons in the C-H covalent bonds. Assume that repulsion of the electrons in the bonds leads to a tetrahedral arrangement to minimize electronic repulsion. Ammonia (H3N, 6B) has a tetrahedral array around nitrogen if the electron pair is taken into account. If only the atoms are viewed, however, 6B has the pyramidal shape shown. Water (HOH, 7B) has two electron pairs that occupy the corners of a tetrahedral shape, as shown. 

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