CHE-310OrganicChemistryIDr.JamesLyle;office

Click to edit Master title style,Click to edit Master text styles,Second level,Third level,Fourth level,Fifth level,*,CHE-310,Organic Chemistry I,Dr. James Lyle; office: NSM D-323,(310) 243-3388 or 243-3376,office hours: MWF: 9-10:00am & Tu: 8:00-9:00am,1,Web page:,2,texts,:,Organic Chemistry, Morrison & Boyd (6th),Supplement to.,Morrison & Boyd,(optional),Supplement.,Model kit,3,Grading,: traditional,no curve,!,A=100%-93%, A-=92%-90%,B+=89%-88%,B=87%-83%,etc.,Daily exams = 100,4 exams 100 pts = 400,final exam = 100,homework,required,600,Daily exams,No make ups! Drop two lowest scores. Begin at 10:00!,4,Daily Homework:,Required,!,(hold until called for),Cheating: Dont do it! The penalties are severe.,Turn off all cell phones and pagers!,5,Organic Chemistry; difficult, challenging! “memorization course” (NOT! wellmaybe),body of knowledge + application of theory!,How to succeed?,1.,look over,the text before lecture.,2.,listen,carefully to lectures,3.,read,the text (take notes),4.,do the homework,(twice.?),5.,review,6,Organic Chemistry,- the study of the compounds of,carbon, their properties and the changes that they undergo.,Descriptive approach -,nomenclature,syntheses,reactions,mechanisms,.,7,First: review topics from gen. chem. important to o-chem.,atomic structure,subatomic particles:,mass charge,protons,neutrons,electrons,nucleus,: protons & neutrons,electron shells & subshells,: electrons,1 amu+1,1 amu 0,0 amu - 1,8,atomic number,= number of protons in the nucleus of the atom (different for each element); Hydrogen = 1, Helium = 2, Lithium = 3,.,also the number of electrons in a,neutral,atom,Iron = 2626 protons = +26,26 electrons=,-26,net charge= 0,9,atomic mass,= mass of an atom; sum of the weights of the protons & neutrons.,But, not all atoms of a given element are identical.,isotopes,- atoms of the same element with different numbers of neutrons.,10,examples of isotopes,prot.neut.%,H,1,1 099.985,H,2,1 1 0.015,C,12,6 698.89,C,13,6 7 1.11,C,14,6 8 .,Cl,35,17 1875.53,Cl,37,17 2024.47,F,19,9 10100,11,atomic weight,: weighted average mass of the atoms; combining weight.,electrons = energy shells & subshells about the nucleus.,shells = 1, 2, 3, 4, .,subshells = s, p, d, f,orbitals,= region in space where an electron of given energy is likely to be found; no more than two electrons of opposite spin per orbital (Pauli exclusion principle).,12,maximum number of electrons per subshell,:,s 2,p 6,d10,f14,13,order of filling,1s,2s2p,3s3p3d,4s4p4d4f,5s5p5d5f,6s6p6d6f,spectral notation,: 1s,2,2s,2,2p,6,14,Fluorine (at.# 9) 9p/9e,1s,2,2s,2,2p,5,Chlorine (at.# 17) 17p/17e,1s,2,2s,2,2p,6,3s,2,3p,5,Bromine (at.# 35) 35p/35e,1s,2,2s,2,2p,6,3s,2,3p,6,4s,2,3d,10,4p,5,Iodine (at.# 53) 53p/53e,1s,2,2s,2,2p,6,3s,2,3p,6,4s,2,3d,10,4p,6,5s,2,4d,10,5p,5,15,valence electrons,= electrons in the outermost,shell,Fluorine has 7 valence elect.,Chlorine has 7 valence elect.,Bromine has 7 valence elect.,Iodine has 7 valence elect.,16,PERIODIC CHART OF THE ELEMENTS,I VIII, , H He , 1 II III IV V VI VII 2 , , Li Be B C N O F Ne , 3 4 5 6 7 8 9 10 , , Na Mg Al Si P S Cl Ar , 11 12 13 14 15 16 17 18 , K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr , 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 , Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe , 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 , Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn , 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 , Fr Ra Ac , 87 88 89 104 105 , Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu , 58 59 60 61 62 63 64 65 66 67 68 69 70 71 , Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr , 90 91 92 93 94 95 96 97 98 99 100 101 102 103 ,17,periodic chart of the elements,metals,&,nonmetals,families,(groups) of elements,alkali metals,(group I),Li,Na,K,.,alkaline earths,(group II),Be,Mg,Ca,.,halogens,(group VII),F,Cl,Br,I,.,noble gases,(group VIII or 0),He,Ne,Ar,.,group number = valence elec.,18,Chemical bonding (classical),chemical bond,: force that holds atoms together in compounds.,ionic bond between,metals & non-metals,covalent bond between,non-metals & non-metals,19,definitions:,ionic bond,: a chemical bond formed by the,transfer,of valence electrons to achieve noble gas electron config-urations, resulting in ions held together by electrostatic attraction.,covalent bond,:,chemical bond formed by the,sharing,of valence electrons to achieve noble gas electron configurations.,20,ionic bond example,:,sodium chloride,sodium = Na, atomic # 11,1s,2,2s,2,2p,6,3s,1,neon = Ne, atomic # 10,1s,2,2s,2,2p,6,if Na loses 1 elect. then it will have a noble gas elect.,config. like Ne but will be charged, +1 ( 11p/10e ).,= Na,+,sodium ion,21,chlorine = Cl, atomic # 17,1s,2,2s,2,2p,6,3s,2,3p,5,argon = Ar, atomic # 18,1s,2,2s,2,2p,6,3s,2,3p,6,if chlorine can gain an electron it will have a noble gas electron config. like argon but will be charged -1 (17p/18e) Cl,-,sodium chloride = NaCl,orNa,+,Cl,-,22,covalent bonds,Lewis Dot representations,HBe,:,Cl,Ne CO,H,2,O=H,:,O,:,H,see homework! review your gen chem text!,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,.,23,. . . .,CO,2,:O:C:O:O=C=O:,N,2,:N:N:N,N:,HCNH:C:N:H-C,N:,. .,H,2,COH:C:O:H-C=O:,. |,H H,24,atomic orbitals,s,p,d,etc.,25,hybrid atomic orbitals,s + p = 2 sp hybrids,s + p + p = 3 sp,2,s + p + p + p = 4 sp,3,26,Hybrid atomic orbitals:,sp = linear; 180,o,sp,2,= trigonal; 120,o,sp,3,= tetrahedral; 109.5,o,27,VSEPR,(valence shell electron pair repulsion),prediction of hybridization,number of ligands (X),plus,number of unshared pair of valence electrons (E),equals,number of orbitals needed,what type of hybrid orbitals are needed,28,eg. H,2,O = H,:,O,:,HorHOH,2 ligands + 2 lone pair = 4 orbitals,AX,2,E,2,sp,3,tetrahedral, 109.5,o,water is a bent molecule with bond angles of 105,o,.,.,.,.,29,VSEPR,AX,2,sp180,o,linear,AX,3,sp,2,120,o,trigonal,AX,2,Esp,2,120,o,or “bent”,AX,4,sp,3,109.5,o,tetrahedral,AX,3,Esp,3,109.5,o,or “pyramidal,AX,2,E,2,sp,3,109.5,o,or “bent”,30,We can use the VSEPR method to predict the shape and bond angles for simple covalent molecules.,SHAPE,is important!,review gen chem text!,Do,the homework!,31,PERIODIC CHART OF THE ELEMENTS,I VIII, , H He , 1 II III IV V VI VII 2 , , Li Be B C N O F Ne , 3 4 5 6 7 8 9 10 , , Na Mg Al Si P S Cl Ar , 11 12 13 14 15 16 17 18 , K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr , 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 , Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe , 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 , Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn , 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 , Fr Ra Ac , 87 88 89 104 105 , Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu , 58 59 60 61 62 63 64 65 66 67 68 69 70 71 , Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr , 90 91 92 93 94 95 96 97 98 99 100 101 102 103 ,32,Polarity,Covalent,bonds,are polar when the two atoms sharing electrons have different electronegativities.,eg. HCl,+ -,a charge separation or a dipole gives a polar,bond,.,. .,O,2,:O=O: has a non-polar bond,33,Representation of dipoles using vectors,a) magnitude = length,b) direction = positive, negative,A,molecule,will be non-polar if the vector sum of the bond dipoles is zero; eg. they cancel one another.,A,molecule,with be polar if the vector sum of the bond dipoles is non-zero.,34,Determining polarity of covalent molecules:,Lewis dot structure,VSEPR, hybridization shape of the molecule,dipoles for polar bonds,vector sum of the bond dipoles,vector sum = 0 non-polar molecule,vector sum, 0, polar molecule,35,CO,2,:O=C=O:sp linear,vector sum = 0,non-polar molecule,H,2,O,.,HOH AX,2,E,2,sp,3,tetrahedral (bent),.,vector sum,0,polar molecule,!,36,CH,3,OH,Both C & O are sp,3,hybridized.,The bond dipole vectors do not cancel each other and the molecule is,polar,.,NB: must know shape to determine polarity!,37,Inte,rmolecular forces. Attractions,between,molecules.,ionic attractionsNa,+,Cl,-,(very strong)Cl,-,Na,+,dipole-dipole attractionsHBr,BrH,hydrogen bonding ( H attached to N,O,F ),HO-HO,| |,H H,van der Waals (London forces)BrBr,(weak)BrBr,38,intermolecular attractionsstrongest,ionic attractions,dipole-dipole / hydrogen bonding,van der Waals,weakest,ionic bonds = ionic attractions,polar covalent = dipole-dipole attractions,non-polar covalent = van der Waals,39,Cl,2,CO,2,H,2,O,CH,4,KBr,non-polar covalent = van der Waals,non-polar covalent = van der Waals,polar covalent = dipole-dipole &,Hydrogen bonding,non-polar covalent = van der Waals,ionic bonding = ionic attractions,40,bonding = shape = polarity = physical properties,physical properties:,melting point,boiling point,solubility,The stronger the intermolecular forces the higher the mp/bp. Ionic substances have significantly higher mp/bp than do covalent substances. note: mp/bp also increase with increasing size.,41,Prediction of mp/bp (relatively high or low?):,Mg(OH),2,CH,3,OH,CH,2,O,CH,3,CH,3,ionic = ionic attractions,polar = dipole-dipole + H-bond,polar = dipole-dipole,non-polar = van der Waals,mp bp,350,o,C -,-94,o,C 65,o,C,-92,0,C -21,o,C,-183,o,C 89,o,C,42,Solubility,“like dissolves like”, water soluble? must be ionic or highly polar + H-bond,(hydrophilic), water insoluble? must be non-polar or weakly polar,(hydrophobic),Most organic compounds are water insoluble!,43,Acids/Bases,historic:,acids from L.,acidus,= “sour”,sour taste,react with metals, H,2,react with bases water + salts,change litmus red,react with limestone CO,2,examples: HCl, H,2,SO,4, HNO,3, HClO,4,44,historic:,bases -bitter taste,soapy feel,react with acids, water + salts,change litmus blue,examples: NaOH, Al(OH),3, K,2,CO,3, NaHCO,3,45,Lowry-Brnsted Acid,- a substance that donates a proton (H,+,) in a chemical reaction.,Lowry-Brnsted Base, a substance that accepts a proton (H,+,) in a chemical reaction.,CH,3,MgBr + NH,3, CH,4,+ Mg(NH,2,)Br,NaOH + H,2,SO,4, H,2,O + NaHSO,4,base acid acid base,base acid acid base,46,Lewis Acid, a substance that accepts an electron,pair,in a chemical reaction to form a covalent bond.,Lewis Base, a substance that donates an electron pair in a chemical reaction to form a covalent bond.,- +,BF,3,+ :NH,3, F,3,B:NH,3,Lewis Lowry-Brnsted,47,Rule:,acid/base reactions must run “down hill.”,stronger acid/base, weaker acid/base,H,2,SO,4,+ H,2,O HSO,4,-,+ H,3,O,+,stronger stronger weaker weaker,acid base base acid,H,2,O + NH,3, NH,4,+,+ OH,-,weaker weaker stronger stronger,acid base acid base,(note direction of reactions),48,Within a,period,of the periodic chart, acid strength increases with increasing,electronegativity,:,CH,4, NH,3, H,2,O HF,Within a,family,of elements, acid strength increases with increasing,size,:,HF HCl HBr H,2,O,in the halogen family base strength decreases with increasing size:,F,-, Cl,-, Br,-, I,-,51,Will H,2,O react with NaSH as shown below?,H,2,O + NaSH, NaOH + H,2,S,Will the following reaction proceed as shown?,HI + NaCl HCl + NaI,WA SA,no, H,2,O HCl,52,Isomers -,different compounds with the same molecular formula.,example: C,2,H,6,O,CH,3,CH,2,OHCH,3,OCH,3,ethyl alcoholdimethyl ether,bp 78,o,Cbp 24,o,C,53,