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Ochem Week 2 (ch. 2&3)

by: Khanh Tran

Ochem Week 2 (ch. 2&3) CHEM 108A

Khanh Tran
GPA 3.61
Organic Chemistry
Gabriel Navarro

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Hi Guys! Check out my notes for Week 2 of Ochem with Professor Navarro! The notes are typed and include images from lectures, the text, and also some I found online. The notes are on a white backgr...
Organic Chemistry
Gabriel Navarro
Class Notes
Organic Chemistry, Ochem, navarro, chem 108A, ucsc, university of california santa cruz, uc santa cruz, Chemistry, biomedical engineering, lower division, lower div, Chem
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This 32 page Class Notes was uploaded by Khanh Tran on Friday October 2, 2015. The Class Notes belongs to CHEM 108A at University of California - Santa Cruz taught by Gabriel Navarro in Summer 2015. Since its upload, it has received 50 views. For similar materials see Organic Chemistry in Chemistry at University of California - Santa Cruz.


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Date Created: 10/02/15
Ch2 Notes Polar Covalent Bonds Electronegativity Most bonds are neither fully ionic nor lly covalent usually somewhere between the 2 extremes Polar Covalent Bonds the bonding electrons are attracted more strongly by one atom than the other so that the electron distribution bt atoms is not symmetrical covalent bond Polar covalent bond It nit bond Electronegativity EN intrinsic ability of an atom to attract shared electrons in a covalent bond causes bond polarity H 21 a Li B it we Elle 111 15 M 15 34 4 ma Mg 5i P S r 19 1t 1quot 1i 21 25 IE EH 39ll39i if Gr Min IFE I Hi u En Gel 3e A5 Se Er Er 13 ll 13 15 TLEE 1l 15 1i 19 TLE 1w 15 TL 1i 39 l 14 EE l h Ellquot liquot Er ME ME Tc Flu hi End In En El 11 EB LE M2 It 14 ll 113 19 12 23 22 119 1 TL 1 19 25 5 La Illf39 Ta W Fig 5 Ir Au IlIg Tll Fl Bil M n 12 19 1w 13 TLE 1L 19 12 22 12 24 19 TIE 19a 19 21 Bonds with atoms EN difference lt 05 nonpolar covalent Bonds with atoms with EN difference between 0520 polar covalent Bonds with atoms with EN difference gt 20 ionic Therefore generally but not always Covalent lt Polar Covalent lt Ionic in terms of bond strength HC hydrocarbons are relatively nonpolar carbon and Hydrogen have similar EN while bonds between C and O or C and N are more polarized so that the bonding electrons are drawn away from carbon towards the electronegative atom giving Carbon a partially positive charge la H quotUf Between EN 35 lquot Semen EN 25 l J 3I i Hquotquot39Jr l l Difference 11 ll39u39lethenel lb A Lg Eerben EM 25 l T Li il lium EN m CE l I quotHi H Difference LE Methyllithium Note Electrons are displaced in the direction of the arrow Image above shows electrostatic potential maps which use color to indicate electron richpoor regions Blue is poor while red is rich Inductive effect shifting of electrons in a 0 bond in response to the EN of nearby atoms Polar Covalent Bonds Dipole Moments Dipole moment 1 the magnitude of the charge Q at either end of the molecular dipole times the distance 1er Expressed in Debyes D 30 where 1D 3336X10 coulomb meterC 39 m Table 21 Binnie illllnmente ef Sitme Eempenntlle Enrnpnun i pelle mnment C l l ll ln ip le mement Eli H ll em hi H3 1 A EH19 eee EllIEHIHE 1 e1 EI g l 1 13 Ii H20 1 35 e EIlEUIl 1 3e 3 EHEC EIEH 1 1 Fl Ii EH 1 153 Some molecules have no dipole moments because their structures are symmetrical thus the bond polarities and the lonepair contributions cancel each other out e e e atten engine lie Ell Formal Charges Methane e e Hm 57 H 1E af x Hillquot Squotll lll IE lileine in it Benzene lie it Formal charges are a formalism don t imply the presence of actual ionic charges in a molecule They are a device for electron book keepingquot The charge of an atom is based on the electron s location Number at E quot Humbernf i Familcimarge Wil l39l ele mns wieme ele mns in free atom V in handed atom r Iquot quota if Number If H I PWEET 3 17 HF is Number of I 1garailenmia ele mnsv DWIde E mn nunh nnt ng in free 31mm E EIEDlIF nE Ex lFEIIF Eulfu r Eul ur valence electrons 39E Eul ur Bundling electrons E Eul ur nnnlmm ing electrons 2 1 j Fmrn al Emma E H m EH 39 Eu a For Emma If H H H 1 quot en HBIEHEE elemmns 2 E mgen unwinding ele rnns 2 airmen nnnh nt ing electrons 39E a Primal mare E 23E E Some Common Formal Charges TITEEIEEJ A Summary El v Ieemmnn Fnrmal Eharges Atam I IN 3 5 P Structure I fl e quot c n 3 ru J gtr r s s F39 l valence ele mns 4 4 E 5 5 E E E E 5 Number ul39 hands 5 E 3 E E 3 1 i l E Number Bf n rmbumding Electmrma 1 2 D 4 2 E 2 E D Funnal 131111th 1 1 l 1 1 H 1 l 1 More Formal Charges memorize these as well as the ones in the table above excluding Sulfur Nitrogen with 3 triple bonds and 1 lone pair O Water O Resonance nubile brand to this uniEwan EU a r l I quot Ft 1 a a g H H 31319 if r to In is mime H H r l T t a Vquot 1 H 39 C39Lx H Hw fl M r H w ll r I a quot g r H w m Hr w H 39 H H BEHEEI iE ltwu rem name form Note Neither of the two structures are correct by themselves the true structure is the intermediate between the two hence the arrow in between the two structures All resonance structures exist at the same time even though density may tend to favor more towards one form than the others favors the more stable form Resonance forms the two or more individual structures for a given molecule Note The only difference between resonance forms is the placement of the pi bond and nonbonding valence electrons The atoms themselves don t move and the connections between the atoms are the same Thus the geometries of the resonance forms are the same daubile bond hem double bond her6 l x0 r H 09 H CQ A B Proper Arrows l A full arrow is used to show 2 electrons being pushed A half arrow indicates the pushing of 1 electron this arrow is used in cases of radical electrons singular electrons as opposed to a pair Resonance Hybrid a single unchanging structure of two or more individual forms with characteristics of both Rules for Resonance Forms 1 Individual resonance forms are imaginary not real Real structure is a resonance hybrid they re just represented by different drawings on papen 2 Resonance forms differ only in the placement of their pi or nonbonding electrons A curved arrow always indicates the movement of electrons not the movement of atoms The red enwe anew indicates that e lene pair elf electrehe WEE hem the ten men atern te hemme part ef a 2 mm HE if R13 I 39 I H LEG Eirnn lteneene y twe e eetrene frent the E mm Ifl39l iI39E ente the hettern eeygen atern tea hemme a lane pain 3 The new reeenenee term tree a then hie henti here H 1 31 I r a H H and lies a lane pair ei eleehre ne here H I Hi EH h Different resonance forms of a substance don t have to be equivalent The negativepositive charge might be on different atoms in different resonance forms but both co This reeenenee ferrn hae the negative charge can veerhe n ntribute to the overall resonance hybrid Thie resenenee term has the negative the rge en exygem at sel sh 39 Hhc ex fH ILx ijw m fli H Hpac geREHH f quotat 2t lquot g i Iquot 3 H H H H H H H H H Acetenie quot i J1 Metene antifn twe reeenanree fmme Not all resonance structures exist in equal proportions 4 Resonance forms obey normal rules of valency The octet rule still applies where it did before H 1 1 e ectmns In 3quot 1 iii this carbon Jig Ck quot5 ip Equot Hl Hquot in H 39 Elm t certate inn lm a Invalid remnants tom 5 The resonance hybrid is more stable than any individual form The larger the number of resonance forms the more stable a substance is Drawing Resonance Forms forms Any threeatom grouping with a p orbital on each atom has two resonance IiI 1quot 139 r 5 r xii 3 H 3 quotit Mulliiplle taunt I I I I ll ll ll ll H35 23 HCIIIg Hg f39ttlz EllI3 Hl llI H Elientanedliulne Lune air of J elation r Iiinubile Island a 7 Male bound Ill A r s Ha ciw iquot l H l H Ere 395 V n t th all 1 31 D 39 01 E39 391 EJ E i 1 r m a 1 a TR f39 T Trim L Eliahi zali F PM Hi I Z an rug 33 H c Hf EH3 HEE CHERl3 H H H Note notice how the pi bonds aren t jumping from one sigma bond to the next rather the electrons from that bond is moving into the atom and the electrons from a lone pair on another atom is jumping in to be a pi bond somewhere else The last image in blue depicts an example of a radical electron being pushed from the atom into a bond Since there is only one electron that can be pushed from that atom one more electron from elsewhere in this case the pi bond nearby also needs to contribute to the pi bond being formed This leaves one electron that was from the pi bond in the middle to just hang out as a radical Acids and Bases The BronstedLowry De nition 6 BronstedLowry acid a substance that donates an Hquot 4 Bronsted Lowry base a substance that accepts an Hquot Conjugate base the product that results with the acid loses a proton Conjugate acid the product that results when the base gains a proton H e e e H Et Acid eee enjiuete enjiugete twee amid i D n E H Nil H 9 Ji Ci Haifa a x Hg Hr HH air eee Eemjugete en uete hese amid H i N H quot39 H it H H H i H quotquotH H H ieiri 35E emjugete enjiuete heee amid Note Water can either act as an acid or a base depending on the circumstances Acid and Base Strength Acidity constant K61 describes the exact strength of a given acid HA in water solution HA Hg A Hg 39 K Mmeii 3 HM Ka 1m09 acidic K a 1less acidic pKa Expresses acid strength is the negative common log of Ka pita z lcig Ha K A stronger acid larger a has a smaller PKa and the opposite for a weaker acid A reaction will go towards the side with a higher pka value because that means that side has the weaker acid so that side probably has the conjugate acid Common Acids and their strengths Table 23 Relative Strengtha cit Same Eemrlien Acids and Their Eenjugate Eaeea Eenju gate iiitie Name pita he ate Haitie Weaker CHECHQ IEllH Ethane ll iii 2 Hall l lg E thDKi E icin nancier acid It aee Hli Water ll 5341 lllICl H39 1 DKi E ion HEN Heeliecyanic acicll Elli titl er39anicle iron HEPDJ Uiihytlregen phosphate iclit 1211 llF39Eld39 Hydrogen pheaphate icin CHECKng Acetic acid 3135 i3 Hgi Elf Acetate inn ngp d Plaesphoric acid 21 5 llgjlij d Elihjyt fli39cgen pheaphate itirl Hl Hl g Nitric acic l 1 33 ll39tl E33 Nitrate ion Hill I Ifgazll techietic acicl it E Chltii39i ale iari St H n cler IInllli39ea lter acicll Predicting AcidBase Reactions from pKa Values the product conjugate acid in an acidbase reaction must be weaker and less reactive than the starting acid and the product conjugate base must be weaker and less reactive than the starting base E U H EEG H HU39 l ll EHEEG39 Stranger Stronger Weaker amid ase amid base 1 Identify acid and conjugate acid 2 Compare pka values 3 Most acidic gives proton away the Larger pka wins the proton Organic Acids and Organic Bases Organic acids characterized by the presence of a positively polarized H atom and are two main kinds 1 acids that contain an Hatom bonded to an EN Oatom and 2 Acids that contain an Hatom bonded to a Catom next to a C20 bondEx 0CCHZ in D II II Hi HM MEI H H 1 f H Egome organic at mH 4 Half HEMPr a atidis g quoti Jquot a J 4i Hi H H H Hquot H Methanol Merit acid Reform in Ha 15m min mi aw a 193 In both cases acidity is due to the fact that the conjugate base resulting 2 from loss of H is stabilized by having its negative charge on a strongly EN Oatom The conjugate base can also be stabilized by resonance Carboxylic acids occur abundantly in all living organisms involved in almost all metabolic pathways ex Acetic acid pyruvic acid citric acid Organic Bases characterized by the presence of an atom with a lone pair 6 of electrons that can bond to Hquot l II I ll ESE organic H mE W mH HHEJA FEIEH HREIEHE EH all IEquot LE1 1393 Hf H H H H H H Hl lli ethvlamlne Methanol EE it l IE 1 3 H N llll H F lll 2 NE 3 HE mgr mmH 3 REM a squot H 3quot H H EH3 H EH3 mainline Manine untililalrge l fimnrm tlm e m Inn39n39i Acids and Bases The Lewis De nition Lewis acid a substance that accepts an electron pair Fl IE III Haganrt ti rlzrjtall orbital a a J E h E t Lewis hase Lewis at iid Anything that has an empty orbital that can accept electrons notice how a proton still ts this description Lewis Acids and the Curved Arrow Formalism l a a nail to l 1 Qt lijnr t F t P film2 Pf F t l Er tr Equot D May Heidi Lewis base eumpllex ian E ma i ms mm ruin HR HE F mum F cr quota quot quota EH 3 Ftquot quot H 3H F F Elm quot H r H H H Boron iiimethigrl eitll hese trii umride ether EWlp lE H Lewis El l ildll lLewis base Note a curved arrow always means that a pair of electrons moves from the atom at the tail of the arrow to the atom at the head of the arrow Some neutral ration donors ngd lllEll Hlal HME H3554 ll EH 4 HEB curl J illlgtllllg lH L L sz namae LE39lillliE tarballmic acid phenol Hill alcolml acids Burma 3 ati n5 lLit wait Some metal GEEm pantith s tll lg Til EH4 FEEHE ENE ll Lewis base a substance that donates an electron pair Donated electron pair is shared between the acid and base in a covalent bond HEPII Earp WI ng Ell l l Ji lH El 1 H H icidl Ease lHyisdmmiium lillll H EHQEHEQH engeem l lgil39iH engeHE lm almhel Ari etllier An aldehyde ill Heteme 3 2E1 513 jf ll II1 II II 5mg Elllgii ll Elllg gll EHQENHE Lewie 335 Jim aeicl chllelride A cairlh ili i39l i Jilin eater An amidle 39 1 acid Ci U D EHENEHE ElHEB F El P E F Elll3 CH EHE 2523 n e Jilin amine it eul dle illn ergenetrillmelphate inn 39339 t 39 1 r f I ngei ail Hg mb l f f f f f H313 El H342 El Aeetiii acid H lease 3 t H h 7 Hagar affix Harriarmed l l Noncovalent Interactions between Molecules Noncovalent interactions dipoledipole forces dispersions forces H bonds Dipoledipole forces occur between polar molecules as a result of electrostatic interactions between dipoles Can either attract or repulse depending on the orientation of the molecules Dispersion forces occur bt all neighboring molecules and arise because the electron distribution within molecules is constantly changing Hydrogen bond an attractive interaction between a hydrogen bonded to an EN 0 or Natom and an unshared electron pair on another 0 or N atom Hydragen lill39lilji Hytlrsge n be nJtl H H Hat 3 5 39i 5 53 DIIIIIIH WLH NH Hi i it H H H iiiii Hydrophilic describes a substance that is strongly attracted to water Hydrophobic describes a substance that is not strongly attracted to water Ch 3 Notes Organic Compounds Alkanes and Their Stereochemistry Alkanes are relatively unreactive and not often involved in chemical reactions Functional Groups Functional group group of atoms within a molecule that has a characteristic chemical behavior Basically anything not sp3 CC of CH is a functional group Note The chemistry of every organic molecule regardless of size and complexity is determined by the functional groups it contains D on le a band 5 Hr Elk la 4H I t la a Halli Cl 35 Fl HailCHI 112 ECECHE quot quot I f x C Ti quotH I l lgE H Ethylene Menthana 7 8393 Er 77 Emmine adds r gar r here H ER HEY 1 1H f C E i 39 if H lar1 Elli HEY Cy III CHE Hal f quotTH Note The reaction of ethylene and menthene bromine In both molecules the CC double bond functional group has a similar polarity pattern so b Br2 molecules react w in the same way The size and complexity of the molecules are not important Will only have to memorize the functional groups on the ash cards marked with f Functional Groups with CC Multiple Bonds f Alkenes have double bonds f Alkynes have triple bond f Arenes Aromatic rings have alternating double and single bonds in a six membered ring of carbon atoms EMMA EIWE L UFES m Same metm Funttljnml Eraum HamE innmum Hamaemdim Enamapille Mkizmr 1 J 113 HEB CHE aidszuuble bandia Ethane f t ailatjp39ne T rth HI CH tutplehnndl Ethvne Man 3 4 Nam tammatlc rlngi I V t E f M e Humane Ll iaxllde H I Hum EH33 bumma mne 1 LIZ 2 F LIEI almhzel H Ef H EHBEEH I 3x Fa39EeEerananl Jim2r REFEREE mm IllEggDEHg r 1 M M mn hc phaam s 3 PIrw uty CHIEFS Er g MEth phizi phate I I HEI Elm DJph Eph tE n CI I I39Erpi39msplm Ill y FEDE rce E ME I ii l dhh ph e Jrquot REFquot I E 39HnnEF I I2quot amlne mums HE HH Methwamim Imlne 5 Hunt liiIH tilmt base E EHglilElIg ESE EErttneimjne Itquot a if t Mull2 39C Fin rms CEIEC H Ethanemitrila Trim a c i l ma mam 39 Merriamthin Hanna Elanmumquot Ha mezend ng Example Eml a at 33 mlli iuli EHgEiEHg E g EIEmE I39mH aul de I a I a Eliaull39ldr E3quot l39l39mli il lr HQEEEEHUE Eliare ll dEEUE dE 439quot a Emlfnxidi El 1 muf e E RCJEKEnFf EHQECHE if 391 a1 DimEl ny awfulaide E39le htfr39d 4r ECLHH CHQCs n E wnal Fitment HI m if FFIIIEEI no nal Earlmxyljija Lrjtl il39 acid a fix EHBEH C CH gr 391 Ethamm EGIIZI EEIIEI Cl umquot I3 l H H a a 7 q m f gm Erna CHEESEng If Methyl elthamu ate Thi egler I I a L iml1r 5 H r nl CHEESElg llEthyl EithE Ethi xEJ39tE Amide mi u ii a 939 Fr SHEENlg I N r if 393 I E1 wman1IdE arid EI39LLEil39ililii 2 ac1 hlrI3riui3 E EH EH BEE at E h g l ann yl chlorides Igrb xyllsz lljl39j CHI mil rarrlrydn da IZI an hydridr a fit in M EHimij EHg I 39 if 1 1quot Ethamnil amh39grdrlde Functional Groups with Carbon Singly Bonded to an Electronegative Atom f Alkyl Halides CHalogen f Alcohols COH f Ethers two C s bonded to the same oxygen 2 K Organophosphates C 01903 C bonded to a phosphate group f Amines CN Thiols two C s bonded to same sulfur on SH group Sul des Catoms bonded to 2 sulfurs that are joined together Note All are polar with Carbon bearing partial charge and EN atom bearing partial charge Functional Groups with a CO double bond Carbonyl groups Carbonyl groups present in large majority of organic compounds and in practically all biological molecules Carbonyls basically anything that has C 0 carbon double bonded to Oxygen Other functional groups to memorize Carbonyls Amides Esters Carboxylic acids Ketones Aldehydes Nitriles and Alkanes acetone a wpital camonvl mm pou nd 139 If I3 y a l a l l qquot r Aim 3quotquot 1 2 a Fr Ct H E fd Hi allquot E REM Willl E o 4quot quota If at 439quot quotl I if ldah yde Eetane ar joxylir HEM Ester I3 i39 s39 E 3935 ll l l HE A AH LE 5 1 1th Ff Em a N ICEH HCLI f Iana 139quot I EL Tllioeater mide uid chloride Alkanes and Alkane lsomers Alkanes often described as saturated hydrocarbons Hydrocarbons contain only C and H Saturated only have single bonds Note The words saturated and unsaturated refer to the amount of pi bonds in a substance ex Saturatedunsaturated fat Straightchain alkanes compounds whose carbons are all connected in a row Teiblie 33 Harries ef StraightC heiri Alke ee Number ef F39ermue Plumber iFermule terb ne in Heme E iltilgm te bens Km Merrie EH HIM 3 il Methane GilIii 3 Memene g Hm Ethane I32 Hg iii Dem me 31 unil2 Sin Prepe rile Hi3 Elfl Li ntieeene E1 1 Him 1 Butane E4Hj m 12 Ddeeene EmilI 25 5 Penta rue EEHi 1L2 13 Trirdietene E1 3iII 23 iii Ilezte HE EEH 1m En iitesene Egg Him F I lepterie I3 Hi 135 Eli Trieecintene 35 HE Detene Gali 153 Branchedchain alkanes compounds whose carbon chains branch lsomers compounds with same numbers and kinds of atoms but differ in arrangement Constitutional isomers compounds whose atoms are connected differently these are the focus of week 2 lecture as far as isomers go Clicker iP rnhlem Set Constitutional Isum er39 er Different Melecules FJiJeetiet39 Are these meleewlee eunetitutiiemal i513 mere r different meleewlee rEE E lily fins r EH1 quot391 LEEquot Am Cenetitut39ienel ieernere Diffe rent rn elieeuiEE a Because the formula sifor th etwo molecules are different one has a greater number of hydrogen atoms Note Constitutional isomers are always different compounds with different properties but with the same formula Alkyl Groups Alkyl group partial structure that remains if you remove an Hatom from an alkane aren t stable and are usually parts of larger compounds named by replacing ane ending of parent alkane with y Ex Removing a hydrogen atom from methane CH4 generates a methyl group H H H ll lll I lll Hi e g Hl ili U l ll l l N ll l l l l l l Methane methyl greup Methyl eilteh ell Metalwlemine n1 eth en ell liable Still Eme Smeigll39lta hein Alkyl Emups Alllmne lame Harrie lla39hreiir eilji n Ha Methane EI ll3 Methyl Iilei EHEEll Ig Ethane EI llg lllI3 Ethin iiEtjl EHEElllle Ha Fmpene Eng lng Hl3 Pmpj Pr EHEElllIEEHEElllIE Butane EngClllIg l39 b lll 3 Beryl Hui EHEElllIEESHEElllIEEHg Pentene meticmemheelgemi Femer er amyl Branched alkyl groups are generated by removing an Hatom from an internal Carbon Memorize the following 3 a bi 1 45 CHQEHEGHE CHECHJEEHE Propane Pruimr ii Isopro wl EH 3354233425343 EH 35H 2E3 HEEEHE EI gt I g il l EH3 Butane Eutyl secBuwl 3934 CH3 EH3 FMS SHE I2 2 H31 HE H3 l g i H I Hg EH3 I oahutan e Isahum tErIEuw Note the pre xes sec for secondary and tert for tertiary used C4 for refer to the number of other carbon atoms attached to the branching carbon atom HEHH Ha ER Ha Ha HcEHH r I H Iquot quota r quotH H H H H H H H H rh n 1 carbon 2 Tertiary man 33 mtemarr rlmn 4 iiiuni ed to one is handed to two is handled in three is Ensunified to four new attairblzlm39li carbons u mr carbons carbons Note the symbol R is used throughout Ochem to represent a generalized organic group EIH 3H H IIIZ H HIUEEEHE iIE EHIECDg I i 4M Eerieml lm at itmrliiimrgur Eirilric ariid a speci c Ewanails Hg lHl tiarir allmllmll Note there is no such thing as quaternary Hydrogen Quaternary Tertiary Secndlarv and Primary Ca rhons lmholsAmines Earlh ns a 15 s r 51 391 1 9 1a a 11 3 1 shquot firs t a Nichols I 15 g 47 la 395 d U r a Elam 1 r E til 1 6 M v 11 I5 I m E I I1quot 513 rh 3 5 51 3 Amines r 1Lquot 1 L53 W at quotll 1 at Lil III E I PHIii M H z 9 K E y A a ii m E l 1quot IN a h LI 395 H1 m5 is 1 a W Note Notice how in the case of Alcohol the naming refers to the Carbon that the alcohol group is attached to primary if the Carbon that OH is attached to is attached to only one other carbon and so forth Naming Alkanes Note System of nomenclature we39ll be using is devised by International Union of Pure and Applied Chemistry IUPAC A chemical name typically has four parts in the IUPAC stem of nomenclature Pre x identi es the various substituent groups in molecule Parent selects a main part of the molecule and tells how many carbon atoms are in that part Locant gives positions of functional groups and substituents Suf x identi es primary functional group Leeent Prfix lPe rent Stu jiiit Whem are the euiliuente are the HM therer What is the primergr end fumetienel granules eulhetituente stamens fumetienell greulp 1 Find Parent Hydrocarbon nd longest continuous chain of C atoms in molecule use the name of that chain as the parent name If 2 different chains of equal length are present choose one with the larger number of branch points as the parent EH3 iiiIE CHEEHEHEHEEHEEHE EiIEEil EliElig ligi H3 IEHEE H3 liEEIig Named es 3 hexane with NET es 3 hexe he with eu heijtluen te ee em heijtueirtt 2 Number atoms in the longest chain number each C atom in the parent chain starting at the end nearer the rst branch point If there is branching an equal distance away from both ends of the parent chain begin numbering at the end nearer the second branch point EH3 EllIE CHEEHEHEHEEHEEHE Elllg lll EliElig lig H3 IEHEE H3 CliliEEIig Heme es 3 hexane with NET ee 3 heme he with eu heijtiuente ewe em heijtueirlt 3 Identify and number substituents assign number locant to each substituent to locate its point of attachment to parent chain EH3 iiiIE iii ig l iEI iEI iEEHEEHg EiIEEil El iEl ig l igi H3 IEHEE H3 Eli iEEl ig Named as e heeene with NET ee 3 hexe he with eu heijtiuerrte ewe em heijtueirlt If there are 2 substituents on the same carbon give both the same number There must be as many numbers in the name are there are substituents 4 Write name as a single word use hyphens to separate diff pre xes commas to separate numbers If 2 or more different substituents present cite in alphabetical order if 2 or more identical substituents present on parent chain use one of the multiplier di tri tetra and so forth Note Don39t use those pre xes for alphabetizing E 1 E El CHECHE CHEEHQ EH3 CHEEHE EH3 EH EH EH H El l il l EH l EllIClIIElIl Elll EllIr I3 2 4 13 3 3 3i 2 5 2 4 E 2 EU 3 l 32 E 4 25 3 SHEEN EMEth ylhemnE EEt hyldJtlimethyln nane 3lEtlI I5ilEII39Ieth ylhexam E l CHEEHE EH3 EH3 4 EllI HEHEl l l l EllIr milll 3E4 2 3 ESEEEEE 13 EHEEHEEHE Gilliam 393 illlEl III Iyl3Inetlwllliieimaine EllEtlwli dill letll39yllliiex ame 5 Name a complex substituent as though it were itself a compound Sometimes a substituent on the main chain has subbranching to name that compound fully name the complex substituent rst CH3 CH3 EH3 391 2 3 4 s a EHECHIKIE HEHEElllgliflll Ellg ll llg H3 ng CHECHEEHEEHE I A F E El HE Named as 31 135 i imeihvliprnpi39grl group tmmm decane Number the branched sub Beginning its point of attachment to the main chain and identify it Substituent is treated as a whole and alphabetized according to the rst letter of its complete name including and numerical pre x EH3 EH3 1 2 3 4 5 E I Emmerich Hgffli EHEEHEH3 Elll Elll Elll EI i EH 3 iquot 29 29 lies 3 23l1iimetilwlEEmethylprupyli emne 3515 a fu Ether example CH3 1 3 7392 71 EllIEEHEEHEIlg 1 E 3 539 E T E39 51 HEHEH EHg HE HE lHEEH ciH 1le Elll3 3 HE39S EH3 H33 Elllg EELEvDimetlmpropliEmethylnname i551 1E i1metl1grlpmmrllgmup 1 liaranti Stud ent Pro I he m Set I Muthr39 nearest rst branch ElL carit I J V 3 in branched Substituted Prefix if 1 quot Mquot Nl man latulr Write ut name based r1 SF PE 5 Crl l39l lgpltEiit substituent is ria med as lawn Luna nit Fmme Pamnt u ig compound with rule illrill 39 J 39 ugguig n MalHE th EEE Wham LEIHIRE subsii tuents are the How mam What lathe primer 1 yr and functions mumps substiiments carbons lunaticrial gmup cvurrripnunds 39 i D Answer 26 dimethyloctane because the two methyl groups are attached on the 2nCI and 6th carbon in the parent chain thus there are two methyl groups and octane describes the presence of eight carbons in the parent chain This Week s Lecture has only covered up to this point Properties of Alkanes Sometimes referred to as paraffins basically manes little affinity Alkanes react with Oxygen halogens and a few other substances under appropriate conditions Alkane Oxygen occurs during combustion in an engine or furnace when the alkane is used as fuel C02 and H20 formed as products Alkane Cl2 occurs when a mixture of the two is irradiated w UV light A sequential substitution of the alkane hydrogen atoms by chlorine can occur which leads to a mixture of chlorinated products EH4 41 12 Cl lg l HEll C I39 I 2 J JE Cl 2 1 11413 Jll I lCil CI 2 121314 1 llCil 31111 Melting point lElpaillineg Ith Elli 11111 Temperature it i 39 i i i I ll 2 a 1 a E 1 B a 111 11 12 13 14 Number arcarbpns Alkanes show regular increases in both boiling point as molecular weight increases due to the weak dispersion forces between molecules the dispersion forces increase as molecule size increases accounting for the higher melting and boiling points of larger alkanes Note Won39t need to know this for the classexams but it is an important concept that will come up later on in organic chemistry Conformations of Ethane Stereochemistry the branch of chemistry concerned with the 3D aspects of molecules Sigma bonds are cylindrically symmetrical because of this rotation is possible around CC bonds Ex Ethane rotation around CC bond occurs freely which changes the spatial relationships between the hydrogens on one carbon and those on the other H T i f Hm Fl 13 t r Ri ete He HER H e quotta we L y sf w a I r H H a H 5 g Conformation different arrangements of atoms that result from bond rotation Conformers molecules that have different arrangements also called formational isomers 1 Sawhorse representation views CC bond from oblique angle and indicates spatial orientation by showing all CH bonds 2 Newman projection views CC bond directly endon represents the 2 carbon atoms by a circle Lines to center of circle Bonds attached to front carbon Lines to edge of circle bonds attached to rear carbon H r Beckeerben 7 H sa l I V 1 ff 39ll J 7 H RH g a x A 7 H Frent eertrn SeMreree Newman repreeemetien p39rejeetien Ethane doesn t have a perfect free rotation instead there is a small barrier to rotation and some conformations are more stable than others Torsional strain the extra energy present in the highest energy least stable conformation speculated to be a result of an interaction between CH bonding orbitals on one carbon with antibonding orbitals on the adjacent carbon Ethane has this Conformations of Other Alkanes Anticonformation the lowest energy arrangement Steric Strain the repulsive interaction that occurs when atoms are forced closer together than their atomic radii aow Steric strain 33 dembl 3 Wmt Ill J frquot EZng Fintats EEF39 3 L A H 39 Hp Eutene eslipsed Eutane gmmhe tol orrrnatin tm onmat ion 1E ltme all is It ll m1trll Tatilsi Energy EEEE E for Interactions in Alkans Enn inrmers E rising cost llintessatt inn Eause k fmol ktal mti I H H 1 eclipsed Torsional strain still 1 J H H EH3 eclipsed Mostly torsional strain ELI 11 CH CH3 Etiltpsetl Torsional and static strain ll lit EHEH 3H3 gauche Stem strain 33 HE


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