Lecture 2 ( ) Chapters 2 and 3

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1 Lecture 2 ( ) Chapters 2 and 3 Goals: Review Periodic Table and the atom, types of bonding for carbon (hybridization), and Lewis structure Learn how to draw bond-line structures Problems: (for all formal charge problems, use the table where possible rather than calculating) Chapter 1: 6, 7, 10, 13, 14, 20, 22, 23, 26, 29, 32, 33, 39, 51-53, 55, 56, 61 Chapter 2: 5-8, 10-14, 17, 18, 23-28, 32-34, 36, 44-47, 49, 51, 53, 55, 72, 76 AND hybridization practice and resonance problems on website Chapter Next time: Begin chapter 3 Convert the following condensed structures to bond-line structures:

2 Triple bonds are a little tricky: How to draw tetrahedral carbon atoms on zigzag bond-line structures:

3 Functional groups and polar covalent bonds Electronegativity (measures an atom s attraction of electrons in a polar covalent bond) Trends on periodic table: Fluorine is most electronegative Bonds are classified as polar or nonpolar o Nonpolar bonds electrons are equally shared C H bonds are considered non-polar o Polar bonds - electrons are not equally shared Convention: H H + - C Cl H Identify the direction of the dipole moment for the following compounds. Are they polar or nonpolar? o A compound with polar bonds is nonpolar if: it has no lone pairs AND is symmetrically substituted with identical atoms

4 Nature of functional group affects physical properties (boiling point in particular): van der Waals interactions, also called induced dipoles or London forces: van der Waals attractions are greater when the electron cloud is larger o F F has weaker attraction than Cl Cl, Br Br, and I I van der Waals attractions are greater for straight-chained (unbranched) molecules: comparison of Van der Waals interactions for C 8 H 18 constitutional isomers straight-chained (higher melting and boiling) branched (lower melting and boiling) Rank in order of increasing boiling point (1 = lowest, 4 = highest): C 7 H 16 C 7 H 16 C 9 H 20 C 7 H 16

5 Dipole-Dipole interactions: require a polar bond (a C Z bond or a C= bond) o Attraction of δ+ to δ Hydrogen bonding: an extreme case of dipole-dipole interactions o H is δ +, must be bonded to F,, or N o Heteroatom (F,, or N) is δ More on boiling points: o Stronger the intermolecular force, the higher the boiling point o Rank the following in order of increasing boiling point (1 = lowest, 4 = highest) H H H bp = 97 o C bp = 48 o C bp = 187 o C bp = o C Same trend exists for melting points (for compounds that are solid at room temperature)

6 Back to formal charges: How many hydrogens at the cationic and anionic carbons? Resonance Structures Describe a molecule s distribution of electrons through a pi system. Tell you where reactivity may occur Consider the acetate anion: CH3C2 - H C H H C resonance arrow - - resonance hybrid Red = high electron density, blue = low electron density Both Lewis structures are valid Resonance structures represent delocalization (spreading) of electrons through π bonds. A double-headed arrow goes between interconverted structures which are called resonance structures. Bond lengths for carbon oxygen and carbon nitrogen bonds are shorter than single, longer than double Individual resonance structures themselves are not complete representations of the molecule the real structure of the molecule is a composite of all possible resonance structures for that molecule.

7 Step by Step Instructions for Drawing Resonance Structures Look at structure. Is there: o An allylic cation (positive charge adjacent to a pi bond) o Allylic lone pair (lone pair adjacent to pi bond) Curved arrow notation: An arrow shows the movement of an electron pair Shows formation of new bond o tail of arrow at δ - (lone pair or center of bond), head at δ + also shows breaking bond: o tail at center of breaking bond, head at destination of electrons from bond

8 o Lone pair adjacent to a positive charge o Pi bond between two atoms of differing electronegativity (opposite of situation above)

9 Multiple resonance structures may be drawn if an extended pi system is present start by identifying the correct scenario:

10 Draw the structure from the first scenario Then evaluate the new structure. Is a new scenario generated (one that would result in a different structure? If YES, draw that structure Repeat until you can draw no new structures HAVING THE SAME NUMBER F FRMAL CHARGES Check your structures! Have you broken any single bonds? Have you exceeded the octet rule on any atom? Do all of your resonance structures have the same number of and type of formal charges?

11 Draw all resonance structures for the following molecule: An orbital view: p orbitals are not part of the continuous system, so aren't part of the resonance stability + + H four continuous p orbitals are in the same plane, so positive charge is distributed through them (this is resonance)

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