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second half notes

by: Ashley Sintetas

second half notes Hwc205

Marketplace > Kansas > Arts and Humanities > Hwc205 > second half notes
Ashley Sintetas
GPA 3.3
western civ 2

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western civ 2
Class Notes
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This 12 page Class Notes was uploaded by Ashley Sintetas on Monday February 16, 2015. The Class Notes belongs to Hwc205 at Kansas taught by Barnard in Fall. Since its upload, it has received 101 views. For similar materials see western civ 2 in Arts and Humanities at Kansas.

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Date Created: 02/16/15
Organic Chemistry test 2 3664 36 Application of solubility Soap soap molecules 2 distinct parts 1 a hydrophilic portion made of ions called polar head 2 a hydrophobic carbon chain of nonpolar CC and CH bonds called the nonpolar tail Dissolving soap in water forms micelles spherical droplets with ionic heads on the surface and nonpolar tails packed together in the interior Soap mixed with water nonpolar hydrocarbon tails dissolve dirt in interior of the micelle Polar head of soap remains on surface of micelle to interact with water Micelles are water soluble they separate from our clothes and are washed down the drain with water 37 Applicationthe cell membrane cell basic unit of life aqueous medium inside the cell separated from water outside by cell membrane 1 barrier to passage of ions water and other molecules in and out of cell 2 selectively permeable nutrients in waste out Phospholipids in membranepolar head and two non polar tails when mixed with water lipid bilayer with ionic heads out tails inpolar heads interact with polar h20 and nonpolar tails head close by VDW interactions Transport across a cell membrane Some non polar molecules like 02 are small enough to enter and exit the cell by diffusion onophores molecules that help some ions transport across cell membrane organic molecules that complex cations hydrophobic exterior soluble in nonpolar interior of membrane central cavity w A 02 atoms whose lone pairs complex with a given atom some antibiotics act as ionophores Nonactin and valinomycin Synthetic ionophores Crown ethers cyclic ethers w A 02 atoms that bind specific cations depending size of cavity ionophore binds to ion on one side of membrane in its polar interior move across membrane bc hydrophobic exterior interacts with hydrophobic tails of phospholipid releases ion on other side helps cell function 38 Functional groups and reactivity functional groups create reactive sites in molecules electron rich sites react with electron poor sites all FGs heteroatom TE bond or both make electron deficient or electrophilic sites and electron rich or nucleophilic sites in a molecule Determine reactivity 1 find functional group determine resulting sites it creates a an electronegative heteroatom NO or X makes C atom electrophilic b lone pair on heteroatom makes it basic and nucleophilic c TE bonds make nucleophilic sites more easily broken than 6 bonds 2 electorn deficient C atom reacts with nucleophile 3 electorn rich C atom reacts with electrophile 39 Biomolecules biomolecules 0 compounds found in biological systems small molecules 4 groups Simple sugars Amino acids Lipids and Nucleotides Van Der Waals Caused by interaction of temp dipoles larger surface area stronger forces larger more polarizable atoms stronger forces DipoleDipole interaction of permanent dipoles Hydrogen bonding h to N O or F Ionon charge attraction of two ions Compounds w comparable weight Increasing strength of intermolecular increasing boiling points and Increasing mp Compounds w similar FGs Increasing surface area increasing bp Increasing polarizability increasing bp More symmetrical compound increasing mp Types of water soluble compounds Ionic compounds Organic compounds w less than 5 carbons and 0 or n atom for h bonding for a compound w one functional group Types of compounds soluble in organic solvents 0 compounds any size or F6 Chapter 4 Alkanes organic compounds no functional group less reactive than other 0 compounds Lipids group of biomolecules similar to alkanes composed of nonpolar CC and CH 6 bonds 41 Alkanes aliphatic hydrocarbons w CC and CH o Acyclic Alkanes CnH2n2 saturated hydrocarbons max number of hydrogen atoms per carbons Cycloalkanes carbons joined in one or more rinds CnH2n Butane and isobutene Butane straight chain alkane sobutene branched chain alkane somers 2 different compounds w same same molecular formula Constitutional isomers differ in the way atoms are connected to each other C atoms in alkanes and 0 compounds classified by of other C directly bonded to them Primary bonded to one other C atom secondary 2 tertiary 3 quaternary 4 Hs are classified depending on type of C atom they are bonded Primary H is on a C bonded to another C atom Secondary H is on a C bonded to 2 other C atoms Tertiary H is on a C bonded to 3 other C atoms CH2 group methylene group compounds that differ by only a CH2 group called homologous series All alkanes end in ane 42 cycloalkanes carbon atoms arranged in a ring add prefix cyclo to name of acyclic alkane having same number of Cs 43 intro to naming many drugs have 3 names 1 Systematic follows accepted rules of naming and indicates compounds chemical structure 2 Generic official internationally approved name for the drug 3 Trade assigned by company that makes it usually catchy easy to remember Ex 1 242 methylpropyl phenyl propanoic acid 2 ibuprofen 3 motrin advil 44 naming alkanes 1 parent name longest number of Cs in a molecule 2 suffix which functional group is present 3 prefix identity location and number of substituants attached to carbon chain prefix pa rent suffix carbon substituents bonded to a long C chain alkyl groups formed by removing one H from an alkane to name change the ane ending of parent alkane to yl R general C group bonded to F6 any alkyl group Acyclic alkane naming 4 steps find parent carbon chain and add suffix ane for alkane number the atoms in the c chain name and number the substituents combine substituent names and numbers parent suffix PWP 45 naming cycloalkanes add prefix cyclo before parent prefix cyclo parent suffix 46 common names isopentane dodecahedrane all names end in ane alkane 47 Fossil Fuels natural gas made of methane w lower amounts of ethane propane and butane burn in presence of 02 and release E petroleum mixture of compounds hydrocarbone w 140 c atoms refining distilling crude petro separate into usable fuel for heat each fuel has diff comp of hydrocarbons 48 physical properties of alkanes only nonpolar CH and C2 bonds only weak VDW forces not water soluble 49 conformations of acyclic alkanes Ethane stereochemistry 3d structure of molecules rotation around single bonds CC sigma bonds conformations different shapes w rotation physical properties of alkanes alkanes have low bps compared to more polar compounds of similar size increasing imf increasing bp bp increases as of cs increases bc of increased sa increase sa increase bp bp of isomers decrease w branching bf of decreased surface area alkanes low mp compared to more polar compounds increasing strength of IMF increasing mp mp increases as of cs increase bc of increased sa increased symmetry increase mp alkanes soluble in o solvents alkanes are insoluble in water eclipsed conformation CH bonds on one carbon behind CH bonds of another Staggered conformation CH bonds on one C bisect HCH bond angle on adjacent C Rotate atoms on 1 c by 60 degrees converts one to another How to draw neuman projection on back of page Staggered conformations are more stable lower in Energy than eclipsed conformations energy difference bw staggered and eclipsed caed torsional energy eclipsing induces torsional strain an increase in E caused by eclipsing interactions 410 Conformations of Butane staggered conformation with 2 larger groups 180 from each other anti Staggered conformation w 2 larger groups 60 from each other called gauche Steric strain increase in energy from when atoms are forced too close to eachother Gauche conformations are usually higher in energy than anti bc of steric strain Staggered conform At energy minima and eclipsed at energy maxima Unfavorable steric interactions increase energy The energy difference bw the lowest and highest E conformations is called barrier to rotation 411 an intro to cycloalkanes affected by torsional steric and angle strain increase in E when tetrahedral bond angles deviate from optimum 1095 cycloalkanes w more than 3 C atoms in ring are not flat pucker to reduce strain 412 cyclohexane planar cyclohexane ring angle strain bc internal bond angles bw carbon atoms 120 and torsional strain all H s eclipsed chair conformations Axial point up equatorial point out chair flip axial equatorial 413 Substituted cycloalkanes larger substituants are more stable in the equatorial position lower energy boat less stable than chair eclipsing interations bw hs cause torsional strain flagpole hs causes steric strain stereoisomers isomers that differ only in way atoms are oriented in space Cis 2 groups on same side of the ring Trans 2 groups on opposite sides of the ring Whether sub are axial or equatorial depends on relative location of 2 sub 414 oxidation of alkanes combustion oxidation reduction reaction oxidation loss of electrons 0 increase in number of C2 bonds or decrease in number of CH bonds reduction gain of electrons H decrease in number of C2 bonds or increase in number of CH bonds combustion burn in presence of water to form oxygen and coZ and water 415 lipids lipids biomolecules resemble alkanes and other hydrocarbons defined by a physical property soluble in organic solvents and insoluble in water made of nonpolar CH and CC bonds have few polar FGs Chapter 5 51 Starch and Cellulose minute differences in structure can cause different properties polymers in carbohydrate group polymer a large molecule made of repeating smaller units called monomers covalently bonded together starch main carb in seeds and roots of plants glucose simple sugar we use for energy cellulose gives rigidity to tree trunks and plant stems hydrolysis of cellulose glucose humans cant go cellulose glucose both 6 membered ring w oxygen and 3 OH groups joined by an oxygen differ in position of O atom joining rings together in cellulose O atom joins 2 rings w 2 equatorial bonds in starch O atom joins 2 rings w 1 equatorial and 1 axial bond isomers bc different compounds w same molecular formula stereoisomers bc oly 3d arrangment is different 52 Two major classes of isomers 1 constitutional isomers differ in way atoms are connected to another a different IUPAC names b same or different FGS c different physical properties d different chemical properties 2 stereoisomers differ in way they are arranged in space a identical IUPAC names except for prefix b same FGS configuration a particular 3d arrangement 53 Chiral and Achiral Molecules identical or different from mirror image chiral molecule that is not superimposable on its mirror image achiral molecule that is superimposable on its mirror image Usually have plane of symmetrMirror plane that cuts a molecule in 12 12 is reflection of other 12 Test Chirality Draw molecule in 3d Draw its mirror image Try to align all bonds and atoms To superimpose you can rotate but not break bonds PWP Enantiomers are mirror images that are not superimposable Stereogenic center C atom with four different FGS no SC molecule generally not chiral one SC molecule always chiral exists as pair of enantiomers 2 or more SC molecule may or may not be chiral 56 labeling Stereogenic Centers w R or S 1 assign priority to each group bonded to center highest atomic number highest priority a if 2 atoms are the same assign priority based on atomic number of atoms bonded to these atoms 1 atom of higher atomic number determines higher priority b if 2 isotopes are bonded assign priorities in order of decreasing mass number c to assign prority in an atom that has a multiple bond treat atom as equivalent number of singly bonded atoms 2 Orient molecule w lowest priority on dash 3 Find direction of priority group 193 a Clockwise R b CounterClockwiseS 57 Diastereomers for n stereogenic centers max number of stereoisomers is Zn 58 Meso Compounds an achrial compound that has stereogenic center usually have plane of symmetry 59 R and S assignments in compounds w two or more stereogenic centers identical compounds have same R S designations at every SC enantiomers have opposite R S designations distereomers have same R S designation for at least 1 SC and opposite for at least 1 of other SC diastereomers stereoisomers not mirror images of each other Figure 510 and 511 512 physical properties of stereoisomers Chemical and physical properties of 2 enantiomers are identical except in their interaction with chiral substances enantiomers same mp bp solubility except for how they interact w plane polarized light polarity of light rotation clockwise dextrorotatory rotation counterclockwise levorotatory enantiomers rotate plane polarized light in equal extent but in opposite directions reactions cancel an equal amount of 2 enantiomers is called racemic mixture or racemeate optically inactive specific roation equation in book notes diastereomers differ with optical rotation enantiomers can not be separated by distillation diasteriomers and constitutional isomers have different physical properties and can be separated by physical techniques enantiomers when 2 enantiomers react w achiral reagent they react at same rate but w chiral non recemic reagent they react at different rates Two enantiomers have exactly same chemical properties except their reaction with chiral non racemic reagents ex chiral drugs Chapter 6 61 writing equations for organic reactions reagent chemical substance that organic reacts with left side of equation with other reactants sometimes above reaction arror organic starting material on left side solvent and temp of rxn maybe added above or below arrow substitution reaction a reaction in which an atom or group of atoms is replaced by antoher atom or groups of atoms elimination reactions elements of starting material are lost and a pi bond is formed addition reaction reaction in which elements are added to the starting material addition and elimination reacctions are opposite 63 bond making and bond breaking reaction mechanism detailed description of how bonds are broken and formed as a starting material is converted to a product one step reaction called concerted reaction stepwise reaction more than one step starting material unstable intermediate product only 2 ways to break cleave a bond electrons can be devided equally or unequally between 2 atoms in a bond equally dividing es called homolysis or hemolytic clevage unequally dividing es calle heterolysis or heterolytic clevage es usually end up on more electronegative atom both require energy homolysis uncharged reactive intermediates with unpaired es heterolysis charged intermediates movement of single e use curved arrow reactive intermediate with single unpaired electron radical most radicals highly unstable have atom without octet no charge intermediates in a group of reactions called radical reactions heterolysis of C2 bond can generate carbocation or carbanion two electrons to Z and none to C charged carbon intermediate carbocation two electrons to C and non to Z generates charged carbon carbanion carbocations elecrophiles carbanions nucleophiles both intermediates in polar reactions rxns where nucleophilie reacts with elecrophile radicals and carbocations are elecrtrophiles bc they have electron deficient carbon carbanions are nucleophhiles bc they have a carbon and a lone pair two radicals can donate 1 electron to form a 2 e bond two ions w unlike charges can come together w neg chatged ion donating both es to form 2 e bond bond formation releases energy 64 bond dissociation energy energy that is needed to homolytically cleave a covalent bond delta h is enthalpy change or heat of reaction delta h pos energy absorbed endothermic delta h negative energy released exothermic bond dissociation energies always positive and homolysis always endothermic bond formation always releases energy reaction is exothermic the stronger the bind the higher the bond dissociation energy decrease down a column of the periodic table as the valence electrons used in bonding are farther from the nucleus shorter bonds are stronger bonds delta h indicates relative strength of bonds broken and formed in a reaction delta h positive more energy needed to break bonds that is released in forming bonds bonds broken in starting material stronger than bonds formed in product delta h negative more energy is released in forming bonds than is needed to break bondds bonds formed in product are stronger than bonds broken in starting material determine overall delta h of a reaction 1 beginning w balanced equation add bond dissociation energies for all bonds broken in starting materials 2 add bond dissociation energies for all bonds formed in products 3 overall delta h is sum of both these numbers


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