Chem 31 Class Packet
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Chem 31 Class Packet 1 Periodic Table of Elements 2 H He 1.00794 4.00260 3 4 5 6 7 8 9 10 Li Be B C N O F Ne 6.941 9.01218 10.811 12.011 14.0067 15.9994 18.99840 20.1797 11 12 13 14 15 16 17 18 Na Mg Al Si P S Cl Ar 22.98977 24.305 26.98154 28.0855 30.97376 32.066 35.4527 39.948 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 39.0983 40.078 44.9559 47.88 50.9415 51.9961 54.9380 55.847 58.9332 58.6934 63.546 65.39 69.723 72.61 74.9216 78.96 79.904 83.80 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 85.4678 87.62 88.9059 91.224 92.9064 95.94 (98) 101.07 102.9055 106.42 107.8682 112.411 114.82 118.710 121.757 127.60 126.9045 131.29 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 Cs Ba La* Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 132.9054 137.327 138.9055 178.49 180.9479 183.85 186.207 190.2 192.22 195.08 196.9665 200.59 204.3833 207.2 208.9804 (209) (210) (222) 87 88 89 104 105 106 107 108 109 110 111 112 114 116 118 Fr Ra Ac† Rf Db Sg Bh Hs Mt (223) 226.0254 227.0278 (261) (262) (263) (262) (265) (268) (269) (272) (277) (285) (289) (293) 58 59 60 61 62 63 64 65 66 67 68 69 70 71 *Lanthanide Series Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu 140.115 140.9077 144.24 (145) 150.36 151.965 157.25 158.9254 162.5 164.9303 167.26 168.9342 173.04 174.967 90 91 92 93 94 95 96 97 98 99 100 101 102 103 † Actinide Series Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr 232.0381 231.0359 238.0289 237.048 (244) (243) (247) (247) (251) (252) (257) (258) (259) (260) 1 Organic Chemist’s View of the 6 H C 1.00794 Periodic Table of Elements 12.011 3 6 5 6 7 8 9 6 Li C B C N O F C 6.941 12.011 10.811 12.011 14.0067 15.9994 18.99840 12.011 11 12 13 14 15 16 17 6 Na Mg Al Si P S Cl C 22.98977 24.305 26.98154 28.0855 30.97376 32.066 35.4527 12.011 19 20 6 6 6 6 6 6 6 6 6 6 6 6 6 6 35 6 K Ca C C C C C C C C C C C C C C Br C 39.0983 40.078 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 79.904 12.011 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 53 6 C C C C C C C C C C C C C C C C I C 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 126.9045 12.011 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 6 C C C C C C C C C C C C C C C C C C 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 6 6 6 6 6 6 6 6 6 110 111 112 114 116 118 C C C C C C C C C 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 (269) (272) (277) (285) (289) (293) 6 6 6 6 6 6 6 6 6 6 6 6 6 6 *Lanthanide Series C C C C C C C C C C C C C C 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 6 6 6 6 6 6 6 6 6 6 6 6 6 6 †Actinide Series C C C C C C C C C C C C C C 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 12.011 Orbital Shapes and Size s orbitals 1s 2s 3s p orbitals d orbitals Hybridization: Nitrogen: .. .. Tetrahedron HNCH Pyramidal N H2NCH3 3 (or Trigonal Pyramidal) CH3 H H H 3 atoms bonded to nitrogen H o 3 107 plus lone pair: Need 4 orbitals sp Methyl Amine Oxygen: .. .. Tetrahedron .. H3COCH3 O Angular or Bent H3C CH3 O . CH3 2 atoms bound to oxygen H 3 CH 105o plus 2 lone pairs. Need 4 orbitals sp 3 Dimethyl Ether Boron: Trigonal Planar F F BF3 120o BF BF F F 3 valence electrons Can only form 3 bonds. H Boron Trifluoride side view Need 3 orbitals sp2 Sulfur: .. .. .. Tetrahedron S . H3CSCH3 S . Angular CH3 H3C CH3 o CH3 105 6 valence electrons- 2 lone pairs H Dimethyl Sulfide Can only form 2 bonds, plus 2 lone pairs sp3 Need 4 orbitals Orbital Picture Drawing Practice For the following compounds, draw an orbital picture showing the s-bonds and lines and the p- bonds as overlapping p-orbitals. Are the H’s in allene and cumulene coplanar? Are the H’s and the nonbonding electrons on oxygen in ketene coplanar? H H CCC H H Allene H H CCC C H H Cumulene H CCO H Ketene Orbital Picture Answers: H H H H CCC CCC H H Allene H H's are not coplanar coming out H towards you H H CCC C H Cumulene H H's coplanar H H CCC C H H coming out coming out towards you towards you H H sp2 hybrid CCO orbitals CCO H H's and nonbonding electron pair are not coplanar H coming out coming out towards you towards you Skeletal Drawings in Organic Chemistry Rules: 1. Carbon atoms are represented by the ends of lines or the junctions between lines without using the chemical symbol, C. The lines represent the bonds between carbon atoms. 2. Hydrogen atoms attached to carbon atoms are not shown explicitly. Sufficient hydrogen atoms are assumed to be attached to the carbons so that each carbon has four bonds. Be sure to count the correct number of bonds - double bonds count as two bonds and triple bonds count as three bonds. 3. All other types of atoms (e.g. O, S, N, Cl) are shown explicitly. 4. Hydrogens attached to atoms other than carbon are always shown explicitly. 5. Nonbonding electron pairs on atoms are not typically shown. Sufficient nonbonding pairs are assumed so that each atom has a full outer shell of 8 electrons. Note- at times carbon atoms, assumed hydrogens and nonbonding electron pairs will be shown for emphasis. Examples and Practice – Convert the following Lewis structures to skeletal drawings and convert the following skeletal drawings to complete Lewis structures. HHH H H H C C C H H C C C H H HHHH H H H C C H C C H H HH H H H C H H C H CCCC H H C H H H H HH H H C H C C H H C C H C H H HCl H H C H C C C C H C H H H O OH or O O H H or OOHO OH N NH2 HH Skeletal Drawings in Organic Chemistry Rules: 1. Carbon atoms are represented by the ends of lines or the junctions between lines without using the chemical symbol, C. The lines represent the bonds between carbon atoms. 2. Hydrogen atoms attached to carbon atoms are not shown explicitly. Sufficient hydrogen atoms are assumed to be attached to the carbons so that each carbon has four bonds. Be sure to count the correct number of bonds - double bonds count as two bonds and triple bonds count as three bonds. 3. All other types of atoms (e.g. O, S, N, Cl) are shown explicitly. 4. Hydrogens attached to atoms other than carbon are always shown explicitly. 5. Nonbonding electron pairs on atoms are not typically shown. Sufficient nonbonding pairs are assumed so that each atom has a full outer shell of 8 electrons. Note- at times carbon atoms, assumed hydrogens and nonbonding electron pairs will be shown for emphasis. Example and Practice – Convert the following Lewis structures to skeletal drawings and convert the following skeletal drawings to complete Lewis structures.