Molecule multiple bonds, Lewis structure

D. A conjugated molecule is a molecule with double bonds on adjacent atoms such as the molecule shown in A. Choice B and C give the definition of sigma and pi molecular orbitals. D is false because a resonance form is one of multiple equivalent Lewis structures, but these structures do not describe the actual state of the molecule. The anion will exist in a state between the two forms. 

When writing a Lewis structure we restrict a molecule s electrons to certain well defined locations either linking two atoms by a covalent bond or as unshared electrons on a sm gle atom Sometimes more than one Lewis structure can be written for a molecule espe cially those that contain multiple bonds An example often cited m introductory chem istry courses is ozone (O3) Ozone occurs naturally m large quantities m the upper atmosphere where it screens the surface of the earth from much of the sun s ultraviolet rays Were it not for this ozone layer most forms of surface life on earth would be dam aged or even destroyed by the rays of the sun The following Lewis structure for ozone satisfies fhe ocfef rule all fhree oxygens have eighf elecfrons m fheir valence shell... 

A single shared pair of electrons is called a single bond. Two electron pairs shared between two atoms constitute a double bond, and three shared electron pairs constitute a triple bond. A double bond, such as C 0, is written C=0 in a Lewis structure. Similarly, a triple bond, such as C C, is written G C. Double and triple bonds are collectively called multiple bonds. The bond order is the number of bonds that link a specific pair of atoms. The bond order in H, is 1 in the group C=0, it is 2 and, for O C in a molecule such as ethyne, C2H2, the bond order is 3. 

STRATEGY Write down the Lewis structure and identify the electron arrangement around each central atom (each C atom, in this case). Treat each multiple bond as a single unit. Then identify the overall shape of the molecule (refer to Fig. 3.2 if necessary). 

Many of the Lewis structures in Chapter 9 and elsewhere in this book represent molecules that contain double bonds and triple bonds. From simple molecules such as ethylene and acetylene to complex biochemical compounds such as chlorophyll and plastoquinone, multiple bonds are abundant in chemistry. Double bonds and triple bonds can be described by extending the orbital overlap model of bonding. We begin with ethylene, a simple hydrocarbon with the formula C2 H4. 

Bond paths are observed between bonded atoms in a molecule and only between these atoms. They are usually consistent with the bonds as defined by the Lewis structure and by experiment. There are, however, differences. There is only a single bond path between atoms that are multiply bonded in a Lewis structure because the electron density is always a maximum along the internuclear axis even in a Lewis multiple bond. The value of pb does, however, increase with increasing Lewis bond order, as is shown by the values for ethane (0.249 au), ethene (0.356 au), and ethyne (0.427 au), which indicate, as expected, an increasing amount of electron density in the bonding region. 

Bond paths are normally found in cases in which there is a bond as defined by Lewis. There is only one bond path for a multiple bond irrespective of the bond order. The bond order is, however, reflected in the value of pbcp. Bond paths are also found in molecules for which a single Lewis structure cannot be written. 

Why is the complex OsHCl(CO)(P Pr3)2 stable, when it is unsaturated It has been argued that lone pairs on the alpha atom of a ligand M—X (M is a transition metal) can have a major influence on reactivity and structure. If M has empty orbitals of appropriate symmetry, X M tt donation creates an M—X multiple bond, with consequent transfer of electron density to M decreasing its Lewis acidity.23 The presence of a carbonyl ligand in OsHCl(CO)(P Pr3)2) increases the n-donor capacity of chloro by means of the push-pull effect making this molecule not a truly 16-valence electron species. 

Molecular formulas merely include the kinds of atoms and the number of each in a molecule (as C4H , for butane). Structural formulas show the arrangement of atoms in a molecule (see Fig. 1-1). When unshared electrons are included, the latter are called Lewis (electron-dot) structures [see Fig. 1-1(/)]. Covalences of the common elements—the numbers of covalent bonds they usually form—are given in Table 1-1 these help us to write Lewis structures. Multicovalent elements such as C, O. and N may have multiple bonds, as shown in Table 1-2. In condensed structural formulas all H s and branched groups are written immediately after the C atom to which they are attached. Thus the condensed formula for isobutane [Fig. l-l(f>)) is CH,CH(CH,)... 

In general, first bond the multicovalent atoms to each other and then, to achieve their normal covalences, bond them to the univalent atoms (H, Cl, Br, I, and F). If the number of univalent atoms is insufficient for this purpose, use multiple bonds or form rings. In their bonded state, the second-period elements (C, N, O, and F) should have eight (an octet) electrons but not more. Furthermore, the number of electrons shown in the Lewis structure should equal the sum of all the valence electrons of the individual atoms in the molecule. Each bond represents a shared pair of electrons. 

Step 1 Decide how many electron pairs are present on the central atom by writing a Lewis structure of the molecule. Treat a multiple bond as the equivalent of a single electron pair. 

Resonance must be used whenever more than one reasonable Lewis structure can be written for a molecule, provided that the Lewis structures have identical positions of all atoms. Only the positions of unshared electrons and multiple bonds are changed in writing different resonance structures. When a better picture of bonding is developed in Chapter 3, we will get a better understanding of what resonance means and when it must be used. 

Write the best Lewis structure for any molecule or ion. This includes determining how many electrons are available and whether multiple bonds are necessary and satisfying the octet rule if possible. For complex molecules, however, the connectivity must be known. (Problems 1.15, 1.16, 1.17, 1.24, 1.29, 1.30, and 1.31)... 

In many molecules, the choice of which atoms are connected by multiple bonds is arbitrary. When several choices exist, all of them should be drawn. For example, as shown in Figure 3-1, three drawings (resonance structures) of C03 are needed to show the double bond in each of the three possible C — O positions. In fact, experimental evidence shows that all the C — O bonds are identical, with bond lengths (129 pm) between double-bond and single-bond distances (116 pm and 143 pm respectively) none of the drawings alone is adequate to describe the molecular structure, which is a combination of all three, not an equilibrium between them. This is called resonance to signify that there is more than one possible way in which the valence electrons can be placed in a Lewis structure. Note that in resonance structures, such as those shown for in Figure 3-1, the electrons are drawn in different places but the atomic nuclei remain in fixed positions. 

Begin with a single pair of dots between each pair of bonded atoms. If no arrangement of single bonds provides a Lewis structure whose atoms satisfy the octet rule, the molecule might have multiple bonds. 

Lewis and valenceA Lewis structure shows the valence electrons in a molecule. Two shared electrons form a structures single bond, with correspondingly more for multiple bonds. Some atoms may also have nonbonding electrons (lone-pairs). Valence structures show the bonds simply as lines. 

Resonance structures Two or more Lewis structures for a single molecule or polyatomic ion that differ in the positions of lone pairs and multiple bonds but not in the positions of the atoms in the structure. It is as if the molecule or ion were able to shift from one of these structures to another by shifting pairs of electrons from one position to another. 

In a covalent bond, two electrons (one pair) are shared by two atoms. In multiple covalent bonds, two or three pairs of electrons are shared by two atoms. Some covalently bonded atoms also have lone pairs, that is, pairs of valence electrons that are not involved in bonding. The arrangement of bonding electrons and lone pairs around atoms in a molecule is represented by a Lewis structure. 

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