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Week 1 - CHEM 2410 Notes

by: Emily Notetaker

Week 1 - CHEM 2410 Notes CHEM2410

Emily Notetaker
GPA 4.0
Organic Chemistry I

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Week of August 23rd notes. Total of three lectures.
Organic Chemistry I
Class Notes
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This 21 page Class Notes was uploaded by Emily Notetaker on Sunday August 30, 2015. The Class Notes belongs to CHEM2410 at University of Toledo taught by Sucheck,S in Fall 2015. Since its upload, it has received 201 views. For similar materials see Organic Chemistry I in Natural Sciences and Mathematics at University of Toledo.

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Date Created: 08/30/15
Chapter 1 Saturday July 252015 1036 PM Remembering General Chemistry Electronic Structure and Bonding C 2539 tum Ewmm Ir i OPPOSH C OhwaS 0 Vac re positively charged have no charge are negatively charged l nucleus protons neutrons of protons Atomic number of carbon 6 has six protons electrondoud and SIX electrons 5 It39ll New Fungun m VW in metUi VO S isotopes have the same atomic number isotopes have 6 6 6 different mass numbers 13C 13C 14C isotopes of carbon a 201 PRISM EWCBUOH Inc ak Review his gtK I gist39iii oi Electrons in an Atom spiLx Patrcai C 79x Jquot17 First shell Second shell Third shell Fourth shell Atomic orbitals s s p s p d s p Lf t 2H6 CHEM 2410 Page 1 Second shell E An A y I First shell Third shell Fourth shell H 2 H 6 Atomic orbitals s s p s p d s p 1 Number ol r Maximum number 7 0t electrons 8 18 La lx OLA6V ehell d i elmlhi rmcivi The rst shell IS closest to the nucleus 4 Oar A TC Lwarw pkever The he atomic orbital is gheli Ciileoo the 39 Within a shell 0 2034 Pearson Education Inc 39 ithe Atomic Orbitals Ix lt 2S lt 3 lt 35 lt 3 lt 3d highe energy e 2014 Pearson Ewcation Inc Atom Name of element Atomic number Is ls 229 229 23 3s H Hydrogen l T He Helium 3 H P 04 0 ws so m 190 lizc 1 Iczuricrvtvc Li Lithium 3 T1 T i D h 039 3 Tm CHQ I Q Bc Beryllium 4 T l T l C Carbon 6 T l T l T T N Nitrogen 7 T J T l T T T 0 Oxygen 8 T i T i T l T T F Fluorine 9 H Ti H H T Nc Noon 390 Nu Sodium ll T1 Tl T1 T 39 An electron goes into the atomic orbital with the lowest energy No more than two electrons can be in an atomic orbital n electron goes into an empty degenerate ezourearsmewcavw quot1c orbital rather than pairing up Ex 3 h iroqeh J aka becomc mow 3 lithium has lost 39ow 06 ea a e 0 e N an electron 7 l 33 Y V CHEM 2410 Page 2 Li a lithium atom Na a sodium atom 0 201 Pearson Em MC lithium has lost an electron gt L1 e a lithium an electron ion gt N e a sodium an electron ion KM YLWI In luv g kr low a in i 90V 6quot L7 a 4 4 Ver 0kan 6 lo IN alec Ho nej owliv I39l i l OLA V Sine l beComeS more able Ghee gives vc af Mil V V Y QClV ElCCIl Vo hcamplVl39l 1 l Gvom L 12 R T ivom B 0 T 1 i6 he Mosl Cltc h ome eclivc L140 5 a fluorine atom a chlorine atom 6 2014 Pearson Educm inc 3 gt an electron e gt an electron fluorine has gained an electron a fluoride ion ICZIQ a chloride ion H a hydrogen atom 0201 Person Education the H gt a hydrogen atom 3 gt an electron stable because its outer shell is empty a proton H a hydride ion equot an electron able because its uter shell is filled CHEM 2410 Page 3 044 become m OVC L393 hi K Oer Gkhi 0 c L39gt CQle 41 mke 5 0xan high cl cl ronfaac VH V H chu o wrhcr s he HE becomes more amide once alzes c quot CKS 4quot ha03 ns W39a39 91 Na jlz Na3 17 Na 91 Na jlz sodium chloride C ZON Pearson Educamn Inc sas WOUOfSens Sod VS c7ng OUo in ago Cpoak subS VahccS CVxl SGd OL ic e i mc39X uurc gt G 2014 Parson Ecunahon Inc Does 3H gt H N H I H ammonia TE 4H gt H C H H methane Lewis Structures 9 2 14 Pemson 500028500 Inc CHEM 2410 Page 4 1 qu on O N E C s n e inc SleaoneS Pad 0 6 am repycszrw one PanS H 2 a Li Be B C N O F I 0 15 20 25 30 35 40 Na Mg Al Si P S Cl 3 09 12 l5 18 2 25 30 i K Ca Br 396 08 10 28 E increasing electronegativity I g C 2395 A ionic polar nonpolur bond covalent bond covalent bond K F39 NuCl39 O H N H C H C C O 2014 Pearson Educates Inc 1 lent Bonds AA39oA par ckl 5 5 5 5 5 5 chat36 h wax molecules l lni hel H H a LloH x Lox6 5 5 gt dipole womenF L slde 0 side the negative end can Show overa VOO rl 39l HCl ofthe bond M Qments Bond Dipole moment D Bond Dipole moment D H C 04 C C 0 H N 13 C N 02 mom Powx COVCM EFH H O IS 7 0 07 H F l7 C F L6 H Cl ll C Cl 15 130 COVOK YT H Br 08 C Br 14 H 1 04 C l 12 the n m o 2014 Pemson scum m CHEM 2410 Page 5 LiH H2 HF ion KC 4 Polax CovalehA npc attracts attracts positive negative charge red 0 orange 0 yellow 0 green 0 blue charge c 2014 Pearson Emcalion Inc a 0amp5 e 9 6b Formal Charget 2 6 4 bonds 39 V g or Formal Charge G 2014 Pearson Eaucaoon Inc 5K Memo V126 39 nds and Lone Pairs H j N l l fI zl quotquot quotquot39 ofbonds 4 4 I I of lone pairs 9 2014 Pearson Education Inc CHEM 2410 Page 6 M4 7 3393 T f quot 5 E VL 39 two covalent bonds holding atoms together are called a double bond o o three covalent bonds holding atoms together are called a triple bond Hquot Hun B HH Hg3r HgggH HcgH HI H NggN H H H H H dwlolc world I mpl I I I lt3 I c 00 H l l3r H l H H 9 H H IT I39Tl H H H H H H e 2014 Pearson Ewalum Inc Determine the total number of valence electrons 5 6 6 6 23 Because they are negatively charged add another electron 24 Avoid O O bonds Check for formal charges at rz oz 99 N Q f eq 9 incomplete octet O 2014 P9380 Eatcanon III E H II H H H H C 39 C H I CHgC HBICH HZCHClCH or 39Hrcl HCH szCH H Br H H Cl H Br Cl vaHIH H tl c39 l c l n or CH HICl l HICH H or CHCH4CH 1 l H H H H H H H H H H I I I I H C C CC C C H or CHCHCHICHHCHCH0HICH or CHMJCHCH I HCH 1 I l I CH OH H H CHtH OHH Ill H I39HJH H CIH H Cl I H or CHCHCICH3gt1CH3CHOH or m nlcchICHpH H H CHH 0H CH H II II H H I I 70 or THJTII IL H THIOH I H II II IIquotII Hl l39 c39 r c H or CH HCHCHICHn2 H H H CHH 02014 Pearson Educatequot lnc CHEM 2410 Page 7 gtllt OCrle l VLJx 6 Qegomahce ercs 6 390 0 n 9 HI I Z ll 03 A I 5 1 7r3391p Q A quot A 39 I H T 139 I i H or cunxcuxuzm 1 II H m ICHI H HCH H o CHI H HCH39H Ih T 391 T 7 I 13 1 1 IL I 34 kahuna have 41 recognize dOLUole W4 HJ HjCClh ur H CHJTX IL or lh39H r 39v ll 0 Iht lL H l39ll 0r 39u39u39u39uu ur lht39ll H39H nuwui nn nr 39II39II39II or 39n39u39xm 11414181an or 11 I14 04 1L nr ll ll lh 6 201 Poison Educatan Inc 512 Orbital a 1 k hole where 6 can o 25 orbital node not shown node shown e 201 P9350quot EWW Inc giOrbital Have 39 EIhases nodal plane 2p orbital computergenerated 2p orbital 9 2014 Pearson 50163000 Inc CHEM 2410 Page 8 Q 20 Puma Educaton In Potential energy 0 u n c I o o a o 9 n o o u u o a o n o o n o o a n n c o n o o o c u u o o I H H H I H C O gt O 1 atomic 1 orbital 0201 Person Education Inc 39 105 kcalmol 439 kJmol bond dissociation energy bond length c 2014 Pearson Education Inc T 074 A lnternuclear distance 7 CHEM 2410 Page 9 Over Okp bW orbi39mds quot39 0L and an Hbondi39r OVbHul 100 gorm m bends musi I02 606 avorcgbB SCCI W gt V6 icaliy C 39 33953 pl 494 a glsmmbine quottriaii ll ogjoular Orbitals n destructive combination of atomic orbitals D s 7 N 0 wiiwmd an electron in an atomic orbital I x l 1 1 atomic quotr 339 1 atomic orbital It orbital f electrons in a constructive molecular orbital combination of atomic orbitals l Energy gt O 2014 Pearson Barnum1c mot6 hodfs higher craggy x I I t Ir r I r K 1 Energy 2p atomic orbital 2p atomic orbital O 201 Poison Education Inc 1 5 M re El ectronegative T the Bonding MO Ml 39 9 l a O r 1 39 yl 4 39 h I c r r39 I 3V a t Energy I i I l I I l gt 7 t I p atomic orbital of carbon p atomic orbital of oxygen Q 20 PMBM Education MC CHEM 2410 Page 10 le Ne all 4 C H bonds are no identical T a 0 7 WW 0 me ane of methane of methane map for methane 45 know Seomehles 2 MalCS c 2014 Pearson Eoucanon Inc He Mixed to Form A A i Oi39rbitals l l l a I w I 13 l3 l3 gt 57 sp sp w I OCV OlYHC orb mls V x A i 4 hybrid orbitals are formed I An sp3 orbital has a large lobe and a small lobe the s orbital adds to the lobe of the p orbital the s orbital subtractg from 3 20 MMquot mm m the lobe of the p orbital I 0 hybridization I I l Sl Vz Sl pl Carbon is The tetrahedral bond angle is a V G 2014 Pearson Educm lnc 771 jnl Ethane CHEM 2410 Page 11 ethane C H bond formed by sp3s overlap i C C bond formed i by sp3 sp3 overlap G 2014 Pearson Educm in aquot i llcahCS jzrn Ethane 0 VCV 1063 i C H 1096 H dca iH H HIquot perspective formula ballandstkk model of ethane of ethane spacefilling model of ethane electrostatic potential map for ethane 0 201 Pearson Emcatlon Inc 39 7 p f Orbitals T39f B39ond r v A a r x V 39 Energy sp3 atomic 1 sp3 atomic orbital 1 orbital a bonding molecular orbital c 90quot Pearson Ewcanon In I I 9433 A CHEM 2410 Page 12 at mem5 ethene ethylene I I17 IL I hybridization I I I s39p3 5p s p3 l 3 hybrid orbitals are formed giThree sp2 Orbitals 39 Orbital 339 b IR the p orbital is perpendicular to the plane defined by the sp2 orbitals t0p View side view 0 20 PONSM Educatm Int 39 0 bond tax 37 531 l C quot 39 39 I 44 Ell 2quot xr la bond formed by MI 0 bond splspz overlap 0 MT g a 6amp5 ml ovala maplamv H1217quot H ll l a double bond consists of ballandstitk model spacefilling model electrostatic potential map one 4r bond and one 139 bond of ethene of ethene for ethene 2014 Poznan Educator Inc u t 15 V 0k4 hasquot xiiiLLL QJML6 CHEM 2410 Page 13 KVA MF 39 039 Q 05 H CEC 83 ethyne acetylene 1 p p p hybridization I I p p 39 5 5 quot quot quot quot 0 20M Poison Education Inc e 2014 Pursel Emuuon Inc 3 a bond lumed by b 130 sp s overlap 39 gt l 39 i r bond fanned by spsp ovetlap aw orlollals 180 Alec u 0 0520 11392 a triple bond consists of one ballanwstlck model spacefilling model elettrostatk potential map a bond and two 3 bonds of ethyne of ethyne lat ethyne e 2014 Pursel Emullon Inc CHEM 2410 Page 14 e 2014 Pearson Ewcalion Inc bond formed by spz s overlap ll quot Cl la angled svde vrew top vrew ballandstick models ol the methyl cation electrostatic potential map for the methyl cation m ggag H MC PO r 016 e moleCucle w Oulol spzs overlap x 3 H H Veh bl0ll 0 32 ll Hz angled rode view top View ballandstlck models 01 the methyl radical electrostatlc potential map for the methyl radical ozoupearsonsoucammm L gt MOICCUkl NI MDPOG I m 6 Hn lS changes we acmeFry 041 moBCUUC Lcroelncdnra0 V lool5 an lcs quot lone Pourquot mlces more Spam han olher bonds lnl molecule is sing IncbridlZCa bond formed by sp3s overlap u l H 10 CH3 ballandstick model of the methyl anion electrostatic potential map for the methyl anion 5 2014 Pearson Education Inc died Valence Electrons O 39r eLeBOnds in NH3 SPquot m bridiz zd H III H H ammonia l l l Tl p p S I nitrogen39s valence electrons I 0 2014 Pearson 60m lnc CHEM 2410 Page 15 3 hybrid izm l l l 39 I I I 39 h brid zatlon I 1 I I I y I SP3 SP3 SP3 3 A A 4 orbitals are hybridized 4 hybrid orbitals are formed bond formed by the overlap of an sp3 orbital of nitrogen with the s orbital of hydrogen N H NH ammonia ballandstick model of ammonia electrostatic potential map for ammonia 9 2014 Pearson EOUCW Inc a I in A39 tavn VA n A blue GD H Yea c v H quot39H H 10950 NH ammonium ion ballandstick model of the ammonium ion electrostatic potential map for the ammonium ion 6 2014 Pearson Educanon lnc Periodic Mick PactFern down Pl overlap of the s orbital overlap of the s orbital overlap of the s orbital overlap of the 5 orbital of of hydrogen with a Zsp3 of hydrogen with a 35p of hydrogen with a 45p3 hydrogen with a 55p3 orbital orbital orbital orbital 7 l V V 0 Hul HC HBr H l l tOr lf weaker Sift 0 Her lohaar 8 2014 Pearson Educmon inc 43939i i Strength of a 2 CHEM 2410 Page 16 36 Strength of a L4 39 WangHm l lcr g l h 4 Lvio verso Hydrogen halide Bond length Bond S I39englh A kcalmol kJmol H F F 097 I36 571 H Cl K 1275 I03 432 It H Br N 1415 87 366 b H l l609 71 298 l 8 70 Puma Emullon Inc H H H H 5 H Hquotquot39 C H C C H H H H H number of atoms C is bonded to 43 32 2 hybridizarion of C sp 5p sp 1 l bond angles 1095 120 180 6000 540 um 39 molecular geometry of C tetrahedral trigonal planar linear 2014 Pearson Educaoon Inc w39 cii gt DEgbl39eibond 1 0 1 n ll 5 x 1 1 0 2014 Pearson Emcauan Incr CHEM 2410 Page 17 0 2014 Pearson Emuuon Inca COum th bonds 2 10hr Pairs as Tes Gusts Horns 35 5pquot I II t n I 39 a Ilrrx uz NNn H v N quotquot59quot in Mr g39Q Wit 39 39 1 Squot l I I Al SIquot 3 J A lquot I I A Iquot l I 5 e 2014 Parson Eauwron Inc gtquotA 7 urn l i l nNquot 39 J If Ii 9 6 I h quot tf n m4 0 20M Passer Educarm Inc m ore s QhaFaCjcr Sh o rer nro has m ovc Chiero neiScxHve strongest bond weakest bond shortest bond longest bond CXH As H CKH sp sp2 sp3 50 s 333 s 25 s bond strength increases as bond length decreases The shorter the bond the stronger it is 8 2011 Pearson Emulmn Inc CHEM 2410 Page 18 8 7014 PIJI39JUI Emulion Inc greater electron density in the region of orbital overlap C C C H rll The more 3 character the shorter and stronger the bond 0201 Pearson EOUCM 1M 0k 5 grader in the Orbital 39 mhe Bond Angle o o 1800 H1095 H H 120 H m EAH ELC C C If 1 H H m 505 bond angle increases as 5 character in the orbital increases H The more 5 character the greater the bond angle 02014 Peason Education Inr Bond Angle 39 HQ Strength Molecule quot bridlniliun Bond angles lxngth of Slmnglh of Length of Strength of of carbon bond bond I bond 39 ll bond l l kulmul klmull l munmm clmull It I l39 quot V mu 5 r 54 on 177 l in mm 42 II M ethane H II w 120 L33 1745 730 H 1 107 413 H II when Z w 1w L20 3304 om mm mm 553 9 201 P8350 EOUCW lM CHEM 2410 Page 19 The shorter the bond the stronger it is The greater the electron density in the region of orbital overlap the stronger the bond The more 5 character the shorter and stronger the bond The more 5 character the larger the bond angle G 2014 Pearson Education Inc 53 Than a a Bond CC K strength of the double bond 174 kcalmol strength of the spz sp2 a bond 112 kcalmol strength of the 77 bond 62 kcalmol a 77 bond is weaker than a 039 bond 2 2014 Pearson Emmlion Inc mm J Lililll i f of Molecules the 2 bond dipole moments cancel because they are identical and point in opposite directions the bond dipole moments cancel because all 4 are identical and project symmetrically out from carbon carbon dioxide carbon tetrachloride p O D p 0 D 2 201 Pearson Emulm Inr CHEM 2410 Page 20 9 39y i 0f Molecules the 4 bond dipole Cl moments point in 391 X the same general direction rth quoty 0 quotnun NumH H V 39 H 4 X X X H H chloromethane water ammonia 21370 21350 1470 caulkmm In CHEM 2410 Page 21


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