Chem 220 Notes Page 1 Ch. 01 and 02: Structure and Bonding of Organic Molecules I. ‘Types of Chemical Bonds A. Why do atoms forms bonds? + Atoms want to have the same number of electrons as the nearest noble gas atom (noble gas configuration). This requires having a completely full or completely empty valence shell of electrons. © Most main groups atoms will try to have eight valence electrons to completely fill their valence shell; this is the octet rule. There are some exceptions: hydrogen only needs two electrons (duet rule), and boron and aluminum are stable with only six valence electrons (incomplete octet). « Atoms form bonds in order to gain or lose electrons and satisfy the octet rule. B, Two Types of Bonds «Atoms have two major strategies for gaining (or losing) electrons to fulfill the octet tule. These two different strategies lead to the two main types of chemical bonds. 1. Ionic Bonds + One strategy is to completely transfer valence electrons between atoms o™ Naw Oppositely charged ions attract (jonic bond) This forms oppositely charged ions, which are then attracted and form ionic bonds 2. Covalent Bonds The other strategy is to share valence electrons between atoms —™ ae Atoms must stay together to share valence electons (covalent bond) This strategy forces the atoms to remain in close proximity to continue sharing electrons. This forms covalent bonds (co = together and valent = valence),Chem 220 Notes Ch. 01 and 02: Structure and Bonding of Organic Molecules Page 2 C. The type of bond formed depends on the electronegativity difference of the atoms « Electronegativity: the strength with which an atom attracts electrons, Electronegativity is a periodic property which increases from left to right and from bottom to top of the periodic table: clectronegativity increases > HW 24 Li | Be B|c|n]o]r 10 | 16 20 | 25 | 30 | 35 | 40 Na | Mg ail si| ep | s ]a 09 | 12 1s | 18 | 21 | 25 | 30 K Br 08 28 I 24 * Atoms with an electronegativity difference larger than about 2.0 form ionic bonds This usually happens between atoms from opposite sides of the periodic table (between metals and non-metals). II. Lewis Structures + Lewis structures show the connections between atoms that form covalent bonds. They are created by connecting atoms so that they share electrons to have octets. + Inexplicit Lewis structures, all atoms are shown using their atomic symbols, all covalent bonds are shown as dashes, and all unshared electrons are shown as dots 4 H-C—6-H T* u * Tobe correct, a Lewis structure must have the correct number of valence electrons, and in most cases should not violate the octet rule. + There are many ways to predict Lewis structures from the formula of a compound. One method will be presented in Chem 20. 014 Dr Thomas Mucciaro, AChem 220 Notes Ch. 01 and 02: Structure and Bonding of Organic Molecules Page 3 IIL Formal Charges Formal charges must be calculated for each atom of a given Lewis structure. There are patterns for the formal charges of the important atoms in organic chemistry, and eventually we will begin to predict them without calculating. To calculate the formal charge on an atom in a Lewis structure: 1. Draw a complete Lewis structure of the compound of interest. Include all lone pairs and unpaired electrons. 2. For each atom, determine the number of valence electron that the atom “wants” to own. This will be equal to the group number of that atom in the periodic table, or the number of valence electrons on the neutral atom. 3. Determine the number of valence electrons that the atom actually “owns” in the Lewis structure: + Anatom owns two electron for each of its lone pairs. + Anatom owns one electron for each bond connected to it (a double bond counts as two bonds; a triple bond counts as three bonds). + Anatom owns one electron for each unpaired electron Using these rules [# of electrons “owned” = [2x (# of lone pairs)] + [1 x (# of bonds)] + [1 x (# of unpaired electrons)] 4, The formal charge is calculated by subtracting the number of electrons that the atom “owns” from the number of electrons that the atom “wants” (remember: “wants” minus “owns”): Formal Charge = [# of electrons atom “wants” — [# of electrons atom “owns”] n Write the formal charge, in a circle, next to the atom with the charge. This procedure is repeated for each atom in the Lewis structure. 6. The overall charge on the structure equal the sum of all the formal charges on the individual atoms. When the overall charge is already known, this is a good way to check that all of the formal charges have been calculated correctly.