Octet of electrons

The chief reason why ethylenebromonium ion m spite of its strained three membered ring IS more stable than 2 bromoethyl cation is that both carbons and bromine have octets of electrons whereas one carbon has only six electrons m the carbocation... 

Most stable resonance form oxygen and carbon have octets of electrons... 

Oxygen stabilized carbocations of this type are far more stable than tertiary carbocations They are best represented by structures m which the positive charge is on oxygen because all the atoms have octets of electrons m such a structure Their stability permits them to be formed rapidly resulting m rates of electrophilic aromatic substitution that are much faster than that of benzene... 

Ylide (Section 17 12) A neutral molecule in which two oppo sitely charged atoms each with an octet of electrons are di rectly bonded to each other The compound... 

The valence theory (4) includes both types of three-center bonds shown as well as normal two-center, B—B and B—H, bonds. For example, one resonance stmcture of pentaborane(9) is given in projection in Figure 6. An octet of electrons about each boron atom is attained only if three-center bonds are used in addition to two-center bonds. In many cases involving boron hydrides the valence stmcture can be deduced. First, the total number of orbitals and valence electrons available for bonding are determined. Next, the B—H and B—H—B bonds are accounted for. Finally, the remaining orbitals and valence electrons are used in framework bonding. Alternative placements of hydrogen atoms require different valence stmctures. 

Nonmetal haUdes are generally hydroly2ed to a hydrogen haUde and to an oxy-acid containing the other element. The first row nonmetal haUdes, eg, CCI4, resist hydrolysis because the nonmetal element cannot expand its octet of electrons to form a bond to water before its bond to the haUde is broken. Hydrolysis requires either an energetic water molecule to strike the haUde or ioni2ation of the covalent nonmetal—halide bond, processes that tend to be quite slow (16). 

More stable resonance form all atoms (except hydrogen) have octets of electrons. 

These examples illustrate the principle that atoms in covalently bonded species tend to have noble-gas electronic structures. This generalization is often referred to as the octet rule. Nonmetals, except for hydrogen, achieve a noble-gas structure by sharing in an octet of electrons (eight). Hydrogen atoms, in molecules or polyatomic ions, are surrounded by a duet of electrons (two). 

Figure 7.5 (page 177) shows the geometries predicted by the VSEPR model for molecules of the types AX2 to AX. The geometries for two and three electron pairs are those associated with species in which the central atom has less than an octet of electrons. Molecules of this type include BeF2 (in the gas state) and BF3, which have the Lewis structures shown below ... 

An electrophile or electrophilic compound is a reagent attracted to electrons that participates in a chemical reaction by accepting an electron pair in order to bond to a nucleophile. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom which carries a partial positive charge, or have an atom which does not have an octet of electrons. The electrophiles attack the most electron-populated part of a nucleophile. 

Formulas of compounds consisting of the monatomic ions of main-group elements can be predicted by assuming that cations have lost all their valence electrons and anions have gained electrons in their valence shells until each ion has an octet of electrons, ora duplet in the case of FI, Li, and Be. 

From now on, we will refer to the second commandment as the octet rule. But be careful—for purposes of drawing resonance structures, it is only a violation if we exceed an octet for a second-row element. However, there is no problem at all with a second-row element having fewer than an octet of electrons. For example ... 

Rule 2 Electronegative atoms (such as N, O, Cl, etc.) can bear a positive charge, but only if they possess an octet of electrons. Consider the following as an example ... 

An outer atom other than hydrogen is most stable when it is associated with an octet of electrons. 

This step is straightforward when there is only one inner atom. If the molecule has more than one inner atom, place nonbonding pairs around the most electronegative atom until It has an octet of electrons. If there are still unassigned electrons, do the same for the next most electronegative atom. Continue in this manner until all the electrons have been assigned. 

Sharing four electrons allows both carbon and oxygen to have octets of electrons. The right-hand figure above is the correct Lewis stracture for formaldehyde. 

The concept of an octet of electrons is one of the foundations of chemical bonding. In fact, C, N, and O, the three elements that occur most frequently in organic and biological molecules, rarely stray from the pattern of octets. Nevertheless, an octet of electrons does not guarantee that an inner atom is in its most stable configuration. In particular, elements that occupy the third and higher rows of the periodic table and have more than four valence electrons may be most stable with more than an octet of electrons. Atoms of these elements have valence d orbitals, which allow them to accommodate more than eight electrons. In the third row, phosphoms, with five valence electrons, can form as many as five bonds. Sulfur, with six valence electrons, can form six bonds, and chlorine, with seven valence electrons, can form as many as seven bonds. 

A molecule that contains an inner atom from the third or higher row of the periodic table may have electrons left over after each inner atom has an octet of electrons. In such cases, we place any remaining electrons on those inner atoms. Example describes one such molecule. 

Although the inner phosphorus atom has its octet of electrons, a formal charge calculation indicates that we can shift electrons to optimize the provisional structure ... 

A1 (CH2 0113)3 1 indicates that aluminum bonds to three CH2 CH3 fragments. There are 42 valence electrons, all of which are used to complete the bonding framework. Each of the six carbon atoms in triethylaluminum has an octet of electrons and a steric number of 4. Thus, each ethyl group of A1 (CH2 0113)3 described exactly... 

Elements beyond the second row of the periodic table can form bonds to more than four ligands and can be associated with more than an octet of electrons. These features are possible for two reasons. First, elements with > 2 have atomic radii that are large enough to bond to 5, 6, or even more ligands. Second, elements with > 2 have d orbitals whose energies are close to the energies of the valence p orbitals. An orbital overlap description of the bonding in these species relies on the participation of d orbitals of the inner atom. 

The structures used to show the bonding in covalent molecules are called Lewis structures. When bonding, atoms tend to achieve a noble gas configuration. By sharing electrons, individual atoms can complete the outer energy level. In a covalent bond, an octet of electrons is formed around each atom (except hydrogen.)... 

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