CHAPTER 3: INTERMOLECULAR FORCES
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1 CAPTE 3: ITEMLECULA FCES FUCTIAL GUPS DEFIITI Functional Groups are grouping of atoms with characteristic reactivity and properties. + Br Br + 2 Br + Br + 2 Page 1
2 GUPIGS ydrocarbons Carbonyl (C=) Containing Alkane C C 3 C 2 C 3 Aldehyde C Alkene Ketone C Alkyne C C C C Carboxylic Acid C Aromatic Ester C Amide C 2 alogen, xygen or itrogen Alkyl alide X C Br Ether Alcohol C Amine 2 EXAMPLES Viagra (erectile dysfunction) Zocor (lowering cholesterol) C 3 S C 3 C 3 C Page 2
3 ITEMLECULA FCES DIPLE-DIPLE FCES Dipole-dipole forces are attractions between permanent dipoles (δ+ and δ- created when atoms in a bond have different electronegativities). 1. Weak and strong dipole-dipole forces C C 3 C C C 3 2. Why do the dipole-dipole forces differ in strength? 3. Molecular polarities 1 1 Dipole moment image taken from Wade, rganic Chemistry, 8 th edition, 2013, pp. 64. Page 3
4 YDGE BDS ydrogen bonds are an incredibly strong dipole-dipole force. They occur when a hydrogen atom in a polar bond (δ+) interacts with an oxygen, nitrogen or fluorine atom in a polar bond (δ-). 3 C Use dashed lines to show the IMF s between 3 molecules. Use dashed lines to show the IMF s between these two molecules. Label each IMF. C LD DISPESI FCES (LDF) London Dispersion Forces (LDF s) are temporarily induced weak dipoles from the polarization of electron clouds. C 4 C 4 C 4 C 4 C 4 C 4 Page 4
5 ELATIVE STEGT F IMF Type of Force Strength (kcal/mol) Type of Force Strength (kcal/mol) LDF ydrogen bonds 3 Dipole-dipole forces Covalent bonds Ionic Forces 400 F --- -F 38.6 BILIG PIT TEDS WAT APPES DUIG BILIG? 2 (l) 2 (g) Gas Liquid A B C Thermo Data for 2 : 4 Sign Means At certain T s ΔG Δ= kcal/mol ΔS= kcal/mol K At 25 C ( K), TΔS= kcal/mol At 100 C ( K), TΔS= Larson, J. W.; McMahon, T. B. (1984). "Gas-phase bihalide and pseudobihalide ions. An ion cyclotron resonance determination of hydrogen bond energies in XY- species (X, Y = F, Cl, Br, C)". Inorganic Chemistry 23 (14): McMurry, J.E., Fay,.C., Chemistry, 6 th ed., Prentice all, 2012, pp. 359 Page 5
6 BILIG PIT CMPAISS YDCABS B.p. ( C) 5 Graph 6 LIEA VESUS BACED B.p. ( C) 5 All boiling points in this chapter are from the Aldrich andbook of Fine Chemicals, Wade, L.G., rganic Chemistry, 8 th ed., Pearson, 2013, pp. 96 Page 6
7 DIFFEET FUCTIAL GUPS B.p. ( C) ALKYL ALIDES C 3 -I C 3 -Cl B.p. ( C) A DIFFICULT T PEDICT CMPAIS C 3 C 2 B.p. ( C) Page 7
8 PBLEM ank the following in order of increasing boiling point and explain your answer. C 3 2 C 3 B.p. ( C) SLUBILITY LIKE DISSLVES LIKE Polar solvents dissolve polar compounds well onpolar solvents dissolve nonpolar or weakly polar compounds well Polar / nonpolar compounds do not dissolve in each other well Page 8
9 WY DES LIKE DISSLVE LIKE? PLA CMPUD / PLA SLVET WEAKLY PLA CMPUD / PLA SLVET Page 9
10 PLA CMPUD / PLA SLVET Thermodynamic data for transferring molecule from organic solvent into water. 7,8 Compound Δ (kcal/mol) TΔS (kcal/mol) ΔG (kcal/mol) Butane Pentane exane Explanation for Unfavorable change in entropy 9 7 (Butane data) uque, E.M. J. Chem Educ. 1989, 66, (Pentane, exane data) Tanford, C. The ydrophobic Effect: Formation of Micelles and Biological Membranes, 2 nd ed. Wiley: ew York, 1980, pp Silverstein, T.P. J. Chem Educ. 1998, 75, Graphic from Wade, L.G., rganic Chemistry, 8 th ed., Pearson, 2013 Page 10
11 WATE SLUBILITY ALCLS # C Solubility 10 (g solute per 100 g 2 ) 1, 2, 3 C 3, C 3 C 2, C 3 C 2 C 2 miscible Water soluble is semi-arbitrarily defined as when more than 3 grams of compound dissolves in 100 g water at 25 C. EQUIEMETS F WATE SLUBILITY TE FUCTIAL GUPS Solubility values 10 are quoted as gram of solute per 100 g of water. Cl Solubility Solubility 10 CC andbook of Chemistry and Physics, 84 th edition, , pp All values are at 25 C. Page 11
12 PBLEM ank the following compounds in order of increasing water solubility. Briefly explain your answer. BIMLECULES Cholesterol: C 3 C 3 Vitamins: Page 12
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