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SC CHEM 333 - Hydrogen Bonding and Acids/Bases

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Chem 333 1st Edition Lecture 5Outline of Last Lecture II. Writing compoundsa. Dash formulab. Condensed formulac. (bond) line angle formula III. Hydrocarbons (start of chapter 2)a. Alkanesb. Alkenesc. Alkynesd. AromaticIV. Functional groupsa. Alkyl halidesb. Alcoholsc. Ethersd. Aminese. Aldehydes and ketonesf. Carboxylic acidsg. Estersh. Amidesi. NitritesV. Physical propertiesVI. Intermolecular forcesOutline of Current LectureI. Hydrogen Bonding and intermolecular forcesa. Dispersion forcesb. Trendsc. SolubilityII. Chapter 3: Acid and Base Reactionsa. Reaction mechanismsb. Acid/Base Reactioni. Bronsted Lowery Acids and Basesii. Determining weak and strong acids1. pka valuesCurrent LectureI. Hydrogen Bonding and Intermolecular forcesa. London dispersion forcesi. Weakest of IMFii. Attraction result from the interaction between temporarily induced dipolesb. Small molecules have less surface area therefore have weaker interactionsc. Larger molecules have more surface area therefore have stronger interactionsd. Boiling pointi. Stronger molecular interaction causes an increase in boiling pointe. Solubiltyi. Like dissolves like1. H2O dissolves in H2O 2. Oil dissolves in oilii. Polar and ionic solvents usually dissolve in polar solventsiii. Polar liquids can be dissolve togetheriv. Nonpolar solids are soluble in nonpolar solvents and can be mixed together 1. Require no energy to break apart II. Chapter 3: Acids and Basesa. Reaction mechanismsi. A description of molecular events as reactants become productsii. Watch the flow of electrons and atomsb. Cleavagei. Homolytic1. Bonds break and one electron goes to eat atom2. Radicals are produced3. Single headed arrow indicates 1 electron is moving4. Double headed arrow indicates 2 electrons are movingii. Heterolytic Cleavage1. Bonds break and one atom gets both electronsc. Acid/Base Reactionsi. Bronsted Lowery1. Acid: proton donor (gives up proton)2. Base: proton acceptor (takes in a proton)a. H-Acid + H2O  Acid- + H3O+b. Base + H2O  H-Base+ + OH-c. H2O + HCl  H3O+ + Cl- Base Acid Conj. Acid Conj. Bd. mechanism shows bonds, lone pairs, and electron movement 3. What if we have 2 H+ acceptor sites on a molecule?a. Find the most stable resonance structurei. Determine which molecules resonance structures share the most charges through out all resonance structuresii. Determining Strong/Weak Acids1. Measure acidity by finding pka valuea. pka relationshipsi. larger pka = weaker acidii. smaller pka = stronger acidiii. weak acid = stronger conjugate baseiv. strong acid = weaker conjugate base2. List of pkas to memorizepka values in order ofweakest acid to strongest acid/\ Hsp350//\ Hsp245NH2-H Neutral amine 38= - H sp 25/\ O-HNeutral alcohol 16HO-H or H2O Water 15.7O||/\ O O-HBicarbonate 10H3N+ - H 9H2CO3Carbonic Acid 6O||/ \ OHAcetic Acid 5H3O+Hydronium -1.7HCl Hydrochloric Acid -7H2SO4Sulfuric Acid -9HI Hydroiodic Acid -10iii. Equilibrium1. Equilibrium always lies towards the weaker acid2. Ex.)a. H-Cl + H2O  H3O+ + Cl –pka -7 15.7 -1.7equilibrium lies with the products because H3O+ is aweaker acid than


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SC CHEM 333 - Hydrogen Bonding and Acids/Bases

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