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Structure and Bonding

1. The two main causes of the energy release associated with bonding are based on
Coulombs law of electric charge: Opposite charges attract each other (electrons are attracted to protons). Like charges repel each other (electrons spread out in space).

2. As two atoms approach each other, the positively charged nucleus of the first atom attracts the
electrons of the second atom; similarly, the nucleus of the second atom attracts the electrons of the first atom. As a result, the nuclei are held together by the electrons located between them.

3. The attractive force causes energy to be released as the neutral atoms are brought
together. This energy is called the bond strength.

4. When the atoms reach certain closeness, no more energy is released. The distance between
the two nuclei at this point is called the bond length.

5. If the atoms are too close, the electron electron and nuclear nuclear repulsions become
stronger than the attractive forces so you will see a sharp increase in energy.

6. When the nuclei are the appropriate bond length apart, the electrons are spread out around
both nuclei, and attractive and repulsive forces balance for maximum bonding. The energy content of the two-atom system is then at a minimum, the most stable situation.

7. Just like the sharing electrons for bonding results, the complete transfer of an electron from one
atom to the other is again, based on columbic attraction.

8. Two extreme types of bonding explain the interactions between atoms in organic molecules:
A covalent bond is formed by the sharing of electrons. An ionic bond is based on the electrostatic attraction of two ions with opposite charges.

Chapter 1, Structure and Bonding | Vollhardt Organic Chemistry Structure Function 6th

9. Many atoms bind to carbon in a way that is intermediate between those extremes type of
bonding. Some ionic bonds have covalent character and some covalent bonds are partly ionic (polarized).

10. Atoms tend to form molecules in such a way as to reach an octet in the outer electron shell and
attain a noble-gas configuration.

11. Because formation of ionic bond form two identical atoms is difficult (electron transfer is usually
very unfavorable) they tend to share their outer-shell electrons to achieve octet configurations.

12. It is possible for one atom to supply both of the electrons required for covalent bonding. 13. Besides two-electron (single) bonds, atoms may form four-electron (double) and sixelectron (triple) bonds to gain noble-gas configurations.

14. In reality, most bonds are of a nature that lies between the pure ionic and pure covalent and we
call them, polar covalent.

15. The polarization of a bond is the consequence of a shift of the center of electron density in the
bond toward the more electronegative atom. The larger the difference in electronegativity, the bigger is the charge separation. It is indicated in a very qualitative manner (using the Greek letter delta ) by designating a partial positive charge, and partial negative charge, to the respective less or more electronegative atom. As a rule of thumb, electronegativity differences of 0.3 to 2.0 units indicate polar covalent bonds; lesser values are typical of essentially pure covalent bonds, larger values of pure ionic ones. The separation of opposite charges is called an electric dipole, symbolized by an arrow crossed at its tail and pointing from positive to negative. In symmetrical structures, the polarizations of the individual bonds may cancel, thus leading to molecules with no net polarization. The net polarity is the vector sum of the bond dipoles.

16. Molecules adopt shapes in which electron repulsion (including both bonding and
nonbonding electrons) is minimized.

17. The method for determining molecular shape by minimizing electron repulsion is called the
valence-shell electron-pair repulsion (VSEPR) method.

18. Lewis structures are drawn by following simple rules: Draw the (given or desired) molecular skeleton.

Chapter 1, Structure and Bonding | Vollhardt Organic Chemistry Structure Function 6th

Count the number of available valence electrons. Add up all the valence electrons of
the component atoms. In charged structures case the appropriate number of electrons has to be added or subtracted to account for extra charges. The octet rule Depict all covalent bonds by two shared electrons, giving as many atoms as possible a surrounding electron octet, except for H, which requires a duet. Make sure that the number of electrons used is exactly the number counted according to rule b. Frequently, the number of valence electrons is not sufficient to satisfy the octet rule only with single bonds. In this event, double bonds and even triple bonds are necessary to obtain octets. Make sure that all of the atoms in the molecule are octet or duet. Find the total number of bonds needed in a molecule. Assign (formal) charges to atoms in the molecule.

19. Sometimes the octet rule leads to charges on atoms even in neutral molecules. The Lewis
structure is then said to be charge separated.

20. The octet rule strictly holds only for the elements of the second row and then only if there is a
sufficient number of valence electrons to satisfy it.

21. Phosphorus and Sulfur (as relatives of nitrogen and oxygen) are trivalent and divalent,
respectively, and we can readily formulate Lewis octet structures for their derivatives. But they also form stable compounds of higher valence, among them the familiar phosphoric and sulfuric acids.

22. Resonance and Hybrid Resonance:

Because resonance minimizes columbic repulsion, delocalization by resonance has a stabilizing effect. The molecule never looks like any of the individual resonance forms. Resonance forms are not real, although each makes a partial contribution to reality. Resonance is also possible for non-octet molecules. The recognition and formulation of resonance forms is important in predicting reactivity. Structures with a maximum of octets are most important. Charges should be preferentially located on atoms with compatible electronegativity. In cases such as Nitrosyl Cation, the octet rule overrides the electronegativity criterion. Structures with less separation of opposite charges are more important resonance contributors than those with more charge separation.

Chapter 1, Structure and Bonding | Vollhardt Organic Chemistry Structure Function 6th

Separating opposite charges requires energy; hence neutral structures are better than dipolar ones.

Chapter 1, Structure and Bonding | Vollhardt Organic Chemistry Structure Function 6th