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This 18 page Class Notes was uploaded by Mrs. Kiara Medhurst on Thursday October 29, 2015. The Class Notes belongs to CHM122 at Wright State University taught by DavidGrossie in Fall. Since its upload, it has received 7 views. For similar materials see /class/231127/chm122-wright-state-university in Chemistry at Wright State University.
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Date Created: 10/29/15
Rules of Nomenclature for Organic Compounds 1 The longest unbroken chain of carbon atoms in a molecule serves as the parent name for any hydrocarbon or its derivatives 2 The number of carbon atoms in the chain is indicated by the first part ofthe parent name 1 meth 2 eth 3 prop 3 Saturation and unsaturation is indicated by the second part of the parent name saturated no multiple bonds ane one double bond ene two double bonds diene one triple bond yne 4 Branched isomers are named as derivatives of straight chain hydrocarbons in which one or more hydrogens are replaced by hydrocarbon fragments 5 To denote the positions of alkyl groups attached to the parent chain as well as the positions of double and triple bonds a numbering scheme is used 6 When two or more identical alkyl groups are attached to a carbon chain their number is specified by the Greek prefixes di tri tetra and so on The position of each is also specified 7 When different alkyl groups are present along the parent chain they are given in alphabetical order Markovnikov39s rulewhen HX adds to an alkene the hydrogen atom attaches to the carbon atom in the double bond already bearing the larger number of hydrogen atoms Liquids and Solids Kinetic Molecular Theory The volume occupied by the molecules is small when compared to the volume of the container Molecules do not attract each other Molecules are in constant random motion Average kinetic energy is related to temperature Liquids Solids Fixed volume with shape dependent on the con iner Densely packed and random array of molecules Fixed volume and shape Dense and ordered array of molecules Condensation of Gases As a gas is cooled the molecules are pulled closer together by the attractive forces The stronger the attractive forces the less the gas needs to be cooled How Cold Intermolecular Forces The forces that hold molecules together in a liquid or solid Arise from the attraction between opposite charges IonIon Interactions NaLCI39 Coulombs Law E 231x103916mez122 d IonDipole Interaction 3 la 0 m 9 E3 iv Molecular Dipole Contributors polarity of bonds shape of molecule Bond Dipole In a polar bond the bonding atoms are drawn closer to one end of the bond lt C 539 539 lt l 5 Linear Molecules Q39co39 H CEN Angular Molecules Triangular Molecules If Cl II II OI F F F Tetrahedral Molecules DipoleDipole Interaction Forces between molecules that have a permanent dipole moment 5 57 5 5 I 39 C I u quotH quotH quotH H CI H H H Hydrogen Bonds 9 3 l v L a a H a 9 Q g I 9 9 u 19 73 i a r a a DipoleInduced Dipole Interaction Induced DipoleInduced Dipole Interaction Intermolecular Forces IonIon IonDipole DipoleDipole DipoleInduced Dipole Induced DipoleInduced Dipole London forces Properties of Liquids Vaporization k Lower temperature lt nglmriempcramvc lt7Enorgy needed a escape llquid Number oi molecules Vapor Pressure The pressure exerted by the vapor above a liquid at equilibrium Equilibrium Mercuryfilled Va or manomeler pressure u Vapor Pressure Curve u an 36H Jan Jan lvmperlllln Boiling point The temperature at which the vapor pressure equals the external lemuerulur m Linear Vapor Pressure Curve 4 52 00026 0003i 00036 ClausiusClapeyron Equation AHV nP RT C Vapor Pressure at Different Temperatures T T In 1 AH P2 V T1T2 Example The normal boiling point of chloroform CH3CI is 334 K At 328 K the vapor pressure of chloroform is 0824 atm What is the AHV for this temperature range The normal boiling pomt of chloroform CH Cl is 334K At328 K the vapor pressure of chloroform is o 824 atm What Exa m ple mg is the AHV for this temperature e7 Example What is the boiling point of water at a pressure of 0695 atm The molar enthalpy of vaporization is 407 kJmole What is the boiling point of Water at a p essure of o 695 atm7 The molar Example is Other Properties of Liquids Viscosity Surface Tension Capillary geeeooooo 00 a O 0 O O 0 o e o e O 0 ooodoOoo 70 O O O O 0000 e Solids Structure of Amorphous Solids molecules are touching oattractive forces are very large and hold the molecules together omolecules can only vibrate Structures of Crystalline Solids Simple CUblC oMolecules are touching oAttractive forces are very large and hold the molecules in an ordered arrangement IMolecules can only vibrate oStructure is a symmetrical array of atoms ions or molecules arranged in a repeating threedimensional pattern oThe unit cell is the smallest repeating unit in a crystal Simple Cubic BodyCentered Cubic BodyCentered Cubic FaceCentered Cubic FaceCentered Cubic Packing Parameters Ion size Number of Atoms or Ions per Unit Cell Example Nickel crystallizes in a face centered cubic crystal with all sides 352 pm in length What is the interatomic separation between atoms What is the density of nickel Nickel crystallizes W a facercentered cubic crystal With all Side 352 pm li i icngm What is the interatomic separation between atoms Example Nickel crystallizes in a facecentered cubic crystal with all sides 352 pm In eng EXa m ple What is the density of nickel Structure of Ionic Solids Structure of Ionic Solids lb Properties of Solids Freezing Point The temperature at which a liquid begins to solidify 11 m 1 m 1 mmnmui Sublimation point the temperature at which a solid begins to vaporize Vuuanressure zsn zen Zl zxn lemnerulurelll Phase Transitions and Heating Curves l a Nil 73 77 l woo k 7 395 Eollm mi V 75 no w E E 50 mm E 25 F u gt 39 Mellmg mini 239 5 m n so 2n 0 40 7 Heal awed 1 1Jmal 7 Molar Enthalpy of Vaporization the quantity of heat that must be supplied to vaporize a mole of a liquid at a specific temperature H200 gt H209 Molar Enthalpy of Condensation the quantity of heat that must be removed to condense a mole of a gas at a specific temperature H209 gt H200 Molar Enthalpy of Fusion the quantity of heat needed to melt a mole of a solid at the freezing point HZOs gt HZOI Molar Enthalpy of Crystallization the quantity of heat that must be removed to freeze a mole of a substance at the freezing point HZOI gt HZOs Molar Enthalpy of Sublimation the quantity of heat needed to vaporize a mole of a solid at a specific temperature HS Hf HV HZOs gt HZOg Abnormal Heating Curves Boiling polnl Wain m rememmre I13 3 0 V Mellmg Wm 90 an 0 an m Heal added kJmo Example How much energy is needed to increase the temperature of one mole of water from 100 C to 1100 C at constant pressure How ch energy is needed to increase Exa m ple the temperature of one mole of water from 100 C t0 1100 C at constant pressure How ch energy is needed m increase Exa m ple the temperature of one mole of water from 100 C t0 1100 C at constant pressure How much energy is needed to increase Exa ple the temperature of one mole of water from 7100 to 1100 C at constant pressure Phase Diagram for H20 mum cm a a 3 Phase Diagram for CO2 Drum lamI u a SA A 3 Tunparmna l39C Drawing Molecules and Isomers Write longest possible straight carbon chain Check if multiple bonds are necessary if2 hydrogens too few 1 double bond if4 hydrogens too few 2 double bonds or 1 triple bond Use all possible positions forthe multiple bond but look out for duplicate structures Shorten chain by 1 carbon and add a one carbon branch chainpermute to all positions on chain Repeat with a two carbon branch Look for a cyclic structure Markovnikov39s rulewhen HX adds to an alkene the hydrogen atom attaches to the carbon atom in the double bond already bearing the larger number of hydrogen atoms Functional Groups Double Bond ene H H Pentene cc lCC H CHECHZCHS Triple Bond CEC yne HCECCH2CH2CH3 Pentyne Alcohol COH o CH30H Methanol Ether COC ether CH3CH200H20H3 diethylether Amine i amine CH3CH2NH2 ethylamine PryK C Carboxylic acid oic acid CH3COOH ethanoic acid c OH Ester 0 ate CH3COOCH20H3 ethyl ethanoate c O Amide amide CH3CONH2 ethanamide C N Aldehyde 0 al CH3CH20HO propanal C H Ketone 0 one o 2 propanone C CH3C 1 Halide CX CH3CI Chloromethane Phenol C H ORGANIC REACTION SUMMARY Notes 1 The reactions occur at the functional groups not elsewhere 2 Pay attention to how the atoms are bonded together and which bonds change as the reaction proceeds 3 The groups R are either hydrogen or almost any organic group R39 is used sometimes to make it easierto see which R in the product came from which reactant molecule 4 Notice that the atoms in RCO0H are usually written in a line for convenience but 0 o R R they represent the structure OH Similarly RCOOR39 OR39 and RCONHR39 o R NHR39 NEUTRALIZATION Carboxylic Acids and Inorganic Bases General RCO0H MOH gt RCOOM H20 M Na or K or etc carboxylic inorganic salt water acid base Specific CH3000H Na0H gt CH3000Na H20 acetic acid sodium sodium water hydroxide acetate Net ionic CH3C00H OH gt CH3C0039 H20 acetic acid hydroxide acetate ion water ion Carboxylic Acid and Amines General RCO0H carboxylic acid Specific CH3C00H acetic acid ESTERIFICATION General RCO0H carboxylic acid Specific CH3C00H acetic acid AMIDE FORMATION General RCO0H carboxylic acid Specific CH3C00H acetic acid R3N gt amine CH30H2NH2 gt ethylamine R 0H alcohol CH3CH2O H ethanol R 2NH 1 or 2 amine CH3NHCH2CH3 methylethylamine RCOO39 R3NH salt CH3COO39 H3NCH2CH3 ethylammonium acetate RCOOR H20 ester water CH3CH20000H20H H20 3 water ethyl acetate gt RC0NR 2 H20 H ester water gt CH300NCH20H3 H20 NmethyINethyl water acetamide HYDROLYSIS SAPONIFICATION Esters General RCOOR ester Specific CH3COOCH20H20H20H 3 nbutyl acetate Netionic CH3COOCH20H20H20H 3 nbutyl acetate Amides General RCONR 2 ester Specific CH30H200NHCH20H3 Nethylpropanamide Net ionic CH3CH200NHCH20H3 Nethylpropanamide RACDH base NaOH sodium hydroxide OH39 hydroxide ion MOH inorganicb ase NaOH sodium hydroxide OH39 hydroxide ion RCOOM salt CH3000Na sodium acetate CHgCOO39 acetate ion RCOOM salt CH3CHchONa sodium propanoate CHgCHgCOO39 propanoate ion R OH alcohol CH3CH20H20H20H nbutanol CH3CH20H20H20H nbutanol R 2NH amine CH3CH2NH2 ethylamine CH3CH2NH2 ethylamine ADDITION General RzCCR2 unsaturated hydrocarbon Specifics CH3CHCH2 propylene CH3CECCH3 2 butyne CHzBrCCCHzBr 23dibromobutane CH2CH2 ethylene OXIDATION Primary alcohols IDH R Cli H H IDH R CIE H H Secondary alcohols IDH R Cli CHs H Aldehyde R C H 22 gt RzzCCRgz halogen saturated hydrocarbon H2 cataly CH3CH20H3 hydrogen propane Br2 gt CHzBrCCCHzBr bromine 23dibromobutane Br2 CH2Br2C CCH2BI 20H3CH20H3 bromine 2233tetrabromobutane HBr gt CH3CH2BI39 hydrogen bromoethane bromide II E R C H Odciatim g 1 R C OH Odciatim i gt R C CH3 Odciatim O gt H oqcaim R C OH
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