ochemreviewfinal - Julian Casabar OCHEM REVIEW Chapter1 o...

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Julian Casabar OCHEM REVIEW Chapter1 o 1.6 Resonance How to Draw curved Arrows and Push electrons Know how to interconvert structures by moving pairs of electrons and charges and double bonds Resonance – structures are common. LOOK THEM UP!!!!! @#!@$@$!@$ Curved arrows = bond to adjacent atom or Lone pair to an adjacent bond Preference – Filled valence shells Maximum number of covalent bonds. Least separation of unlike charges. Negative charge on the more electronegative atom. Important for protonation with acids because the greatest structure dictates the site of protonation Chapter 2 o 2.1 The Structure of Alkanes CnH2+2n and sp3 Hybridization Sp3 hybridization = 4 valence electrons equal hybridizaiton Shape – Tetrahedral about carbon – 109.5 bond angle o 2.2 Constitutional Isomerism in Alkanes Constitutional isomers – compounds with the same molecular formula but a different connectivity Butane vs 2-methyl propane – both have the same amount of carbons and hydrogens. How to draw them o 2.3 Nomenclature of Alkanes IUPAC system – Meth, eth, prop, but, pent, hex, hept, oct, non, dec, undec, dodec, tridec… Primary – bonded to one other carbon, secondary – bonded to two other carbons, tertiary – bondd to three other carbons, quaternary – bonded to four other carbons. o 2.4 Cycloalkanes CnH2n – Unsaturated Puckering reduces torsional strain but increases angle strain. Boat. Chair, twistboat o 2.5 The IUPAC System – A general System of Nomenclature Know the rules and how to apply them
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o 2.6 Confirmations of Alkanes and Cycloalkanes Butane conformers, chair, boat, twistboat o 2.7 Cis, Trans Isomerism in Cycloalkanes – How to convert planar cyclohexanes into chair cyclohexanes stereoisomer – same molecular formula, same connectivity, different orientation of atoms in space. cis,trans isomers – stereoisomer that are the result of the presence of either a ring or a carbon carbon double bond cis – same side trans – opposite side 2D to 3d chairs Stereocenter – an atom, most commonly carbon, about which exchange of two groups produces a different stereoisomer. When looking at 3D cyclohexane – same plane = trans, different plane = cis which is the opposite of a 2D model o 2.8 Physical Properties of Alkanes and Cycloalkanes Nonpolar hydrocarbons. BP Trends Low molecular weight alkanes – methane to butane are gasses Higher molecular weight – pentane, decane, casoline, and kerosene are liquids at room temp High molecular weight alkanes – paraffin wax are semisolids or solids Chains have higher boiling points Hexane vs 2,2 dimethyl butane – Hexane has higher bp and mp o 2.9 Reactions of Alkanes Oxidations of Hydrocarbons CH4 +2O2 CO2 + 2H2O Chapter 3 – Stereoisomerism and Chirality o 3.1 Stereoisomerism Isomers – different compounds with the same molecular formula
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This note was uploaded on 03/20/2011 for the course CHEMISTRY 310m taught by Professor Iverson during the Fall '08 term at University of Texas at Austin.

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ochemreviewfinal - Julian Casabar OCHEM REVIEW Chapter1 o...

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