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Organic Chemistry I

by: Columbus Kerluke

Organic Chemistry I CHEM 2010

Columbus Kerluke
GPA 3.83

Yu-Lin Jiang

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Yu-Lin Jiang
Class Notes
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This 26 page Class Notes was uploaded by Columbus Kerluke on Sunday October 11, 2015. The Class Notes belongs to CHEM 2010 at East Tennessee State University taught by Yu-Lin Jiang in Fall. Since its upload, it has received 15 views. For similar materials see /class/221419/chem-2010-east-tennessee-state-university in Chemistry at East Tennessee State University.


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Date Created: 10/11/15
1 Structure and Bonding Based on McMurry s OrganC ChemSL734 6th edition Chapter 1 Organic Chemistry Organic until mid 1800 s referred to compounds from living sources mineral sources were inorganic W6hler in 1828 showed that urea an organic compound could be made from a nonliving source Heat gt H2N NH2 NH4 ooN Ammonium cyanate Urea 2004 Thomson Brooksu Cols i Organic Chemistry Today organic compounds are those based on carbon structures and organic chemistry studies their structures and reactions Includes biological molecules drugs solvents dyes food additives pesticides and others Does not include metal carbonate salts and other simple ionic compounds inorganic 3 Organic Chemistry C I He J Be Li B W 39 F Ne 7 8 7 Na Mg A1 Ar K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Kr Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te k I Xe Cs Ba La Hf Ta W Re 03 Ir Pt Au Hg TI Pb Bi Po At Rn Fr Ra Ac Rf Db Sg Bh Hs Mt 2004Th0mm008 11 Atomic Structure Structure of an atom Positively charged nucleus very dense protons and neutrons and small 103915 m Negatively charged electrons are in a cloud 103910 m around nucleus Diameter is about 2 x 103910 m 200 picometerspm the unit angstrom A is 103910 m 100 pm Nucleus protons neutrons ERR olunu around missus m t39upiul In orbiting L39It l39ll lllh 11 Atomic Structure If Nucleus protons neutrons Volume around nucleus occupied by orbiting electrons Atomic Number amp Mass Number The atomic numberZ is the number of protons in the atom39s nucleus The mass number A is the number of protons plus neutrons All the atoms of a given element have the same atomic number Atomic Number and Atomic Mass All the atoms of a given element have the same atomic number Isotopes are atoms of the same element that have different numbers of neutrons and therefore different mass numbers The atomic mass atomic weight of an element is the weighted average mass in atomic mass units amu of an element s naturally occurring isotopes 12 Atomic Structure Orbitals Quantum mechanics describes electron energies and locations by a wave equation Wave function is a solution of the wave equation Each Wave Function describes an orbital w A plot of 12 describes the probabililty of finding the electron The electron cloud has no specific boundary so we show the most probable volume The boundary is called a probablility surface Shapes of Atomic Orbitals for Electrons For the existing elements there are four different kinds of orbitals for electrons based on those derived for a hydrogen atom Denoted s p a and f sand porbitals most important in organic chemist carbon atoms have no 0 or forbitals Thumsml BlaneLCU39A 10 Shapes of Atomic Orbitals for Electrons sorbitals spherical nucleus at center porbitals dumbbellshaped nucleus at middle c All 5 nthital A p orbital A d nrhita 11 Orbitals ancl Shells Orbitals are grouped in shells of increasing size and energy As shells increase in size they contain larger numbers and kinds of orbitals Each orbital can be occupied by two electrons Pauli Exclusion Principle 12 Orbitals and Shells First shell contains one sorbital denoted 15 holds only two electrons Second shell contains one sorbital 25 and three porbitals 2p eight electrons Third shell contains an sorbital 35 three porbitals 30 and five 0 orbitals 3d 18 electrons 13 Orbitals and Shells 3m shitquot i 3 it i 391 1 E paclty 13 re ectmm 3 5 quotEnd Shem 2 p Ja Ili ammcity B elEttrmms 2 s 151 shell furammrity E Bl 39l 14 pOrbitals In each shell there are three perpendicular p orbitals px py and p2 of equal energy Lobes of a p orbital are separated by region of zero electron density a node A 2113 orbital 3 A 2 orbital A lpy orbital Three 2p orbitals 15 13 Atomic Structure Electron Configurations Groundstate electron configuration of an atom lists orbitals occupied by its electrons 1 Lowestenergy orbitals fill first 15 gt 25 gt 2p gt 35 gt 3p gt 45 gt 30 Aufbau buildupquot principle 2 Electron spin can have only two orientations up T and down i Only two electrons can occupy an orbital and they must be of opposite spin Pauli exclusion prnCpe to have unique wave equations 3 If two or more empty orbitals of equal energy are available electrons occupy each with spins parallel until all orbitals have one electron Hund s rule 16 Electron Configurations TABLE 11 Ground State Electron Con gurations of Some Elements Atomic Atomic Element number Con guration Element number Con guration Hydrogen 1 Is v1 Lithium 3 25 i 1s H 21 i i 3 H i Carbom 339 2x Neon 10 Es H ls 13 H as up i 1 an s L w L i H Sodium 11 28 A1 gun 13 210 H ls 3 24 H 2004 Thomson Brookstole 17 Electron Configurations Atomic Element number on guratiun Hydrogen 1 Is 4 3p Carbon 6 2 ls 3 39 4 up H 399 EIDdJUJH 11 1 18 14 Development of Chemical Bonding Theory Kekul and Couper independently observed that carbon always has four bonds Friedrich August Kekule 19 14 Development of Chemical Bonding Theory van39t Hoff and Le Bel proposed that the four bonds of carbon have specific spatial directions Atoms surround carbon as corners of a tetrahedron Note that a dashed line indicates a bond is behind the page Note that a wedge indicates a bond is coming forward J H van39t Hoff 20 Tetrahedral Carbon Bonds in Band receding plane of page into page Bond coming 9 out of page A regular x I tetrahedron A tetrahedral carbon atom a 2004 Thomsam moks Gala 21 15 The Nature of the Chemical Bond Atoms form bonds because the compound that results is more stable than the separate atoms Ionic bonds in salts form as a result of electron transfers Organic compounds contain covalent bonds from sharing electrons G N Lewis 1916 15 The Nature of the Chemical Bond Lewis structures show valence electrons of an atom as clots Hydrogen has one clot representing its 15 electron Carbon has four clots 252 202 A stable molecule results when the outermost valence shell is completed octet eight clots for 2nOI eriod main group atoms two for hy rogen 23 Number of Covalent Bonds to an Atom Atoms with one two or three valence electrons form one two or three bonds Atoms with four or more valence electrons form as many bonds as they need electrons to fill the sand 0 levels of their valence shells to reach a stable octet 24 Number of Covalent Bonds to an Atom F 9 91 gr V W One bond Two bonds 2004 Thomson Brookleole Three bonds Four bonds 25


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