ORGANICBIOCHEM 2 CHM 3218
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This 5 page Class Notes was uploaded by Brigitte Wyman on Friday September 18, 2015. The Class Notes belongs to CHM 3218 at University of Florida taught by Jon Stewart in Fall. Since its upload, it has received 13 views. For similar materials see /class/207012/chm-3218-university-of-florida in Chemistry at University of Florida.
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Date Created: 09/18/15
CHM 3218 Fall 2008 Starting Points for CHM 3218 These are some of the key concepts that you should have mastered from CHM 3217 or CHM 2210 amp 2211 If you are unfamiliar with any of these consult the relevant chapters in your text or see me as soon as possible Since many ofthese concepts will be extended and applied to biological systems it is important that you have a rm grasp on these before we cover too much material in CHM 3218 I Alkanes o Conformational properties of linear alkanes 0 Ring strain 0 Conformational properties of cyclic alkanes II Stereoisomerism o Chirality and optical activity 0 Cahn IngoldPrelog RS nomenclature for absolute con guration 0 Fischer projections o Diastereomers III Haloalkanes o Substitution by bimolecular reactions SN2 mechanism 0 Substitution by unimolecular reactions SNl mechanism 0 Elimination by bimolecular reactions E2 mechanism 0 Elimination by unimolecular reactions El mechanism IV Alcohols and Ethers o Acidbase properties of alcohols 0 Alcohol and ether synthesis by substitution reactions 0 Epoxides V Alkenes 0 Structure and bonding o Alkene synthesis by elimination reactions 0 Alkene synthesis by alcohol dehydrations o Hydrogenation 0 Addition of HX and cationic reactions of alkenes 0 Addition of halogens VI Alkynes 0 Structure and bonding VII Conjugated Pi Systems 0 Structure and bonding resonance VIII CHM 3218 Fall 2008 Allylic systems Conjugated alkenes Benzene and aromaticity Aldehydes and Ketones Structure and bonding Nucleophilic additions to carbonyl groups Enols and enolates Aldol reactions Conjugate additions to enones Acidbase properties of dicarbonyl compounds Claisen condensation Acyl anion equivalents IX Carboxylic Acids Acidbase properties Additionelimination mechanism Acyl halides Acid anhydrides Esters Amides Interconversions of carboxylic acid derivatives X Amines Acidbase properties Imines and enamines Reductive amination CHM 521 3 Fall 2003 The Top 10 Rules for writing correct reaction mechanisms Reaction mechanisms using the curly axrows formalism are one ofthe most important tools for understanding 4 39 39 39 39 39 both 39 39 39 The following 1 ni 39 larger and r L ram t nun 39 the sti11must obey the laws of chemistry and physics Sadly there are no magic steps in biology 1 A andnutnuclearshz s H CH3 H H CH N Fe H dH 39 H 3 H cH g H cH H H cH3 H H CH3 H quotHHa Ht H o gtlt H CH3 g H cH3 2 An anqu should be drawnfm each band halbreaks mfmms 3 wfm 4 Each event v 39 39 atdi erent times as ifthe 39 39 It is equally 39 L 39t they were separated in time EH3 9h H cHJ c jochJ cHggu H cH W cHech 5 It I mtpmtam 0 Clearly dzpzct all zmzrmzdzates m a reacnun hawsz7 zt I usually not necessary A V r 39 39 39 39 quot 4 unconnected structures CHM 3218 Fall 2008 6 Atoms that have non zero formal charges should be marked with appropriate charges To make the positive and negative signs easier to see they are often circled Correct Lewis Dot structures are essential for keeping track of formal charges CHICHZ CHICHZ CH CH 7 Do not use a circle to represent the 7 electrons in an aromatic ring or an arc to show delocalized 7 electrons While this shorthand is often found in the chemical literature its use in writing mechanisms will lead to innumerable problems in electron bookkeeping 9 0 CH Km 2 lt gt CH ZACH 2 8 Be sure to show all valence shell lone pairs of electrons for atoms involved in a reaction Doing this will automatically make you aware of formal charges carried by all atoms 9 Do not use condensed structural formulas for the parts of molecules that are involved in the reaction Bond making and bond breaking involves specific bonds and specific atoms not sets H H n 9 gt OHSgH 53 H c 3 Incorre OHSp A H H o quot CQCHBrCHS gt gtlt OHSQH 13 e H CH3 CHM 3218 Fall 2008 10 Arrow tails originatefrom the mid point ofa bond ifa bond is being broken orfrom a specific lone pair not from the charge symbol Arrow heads should be directed at the mid point of an existing bond if a 7 bond is being formed or at the symbol for an atom if its bond is being broken Arrows do not originate or go ying off into space H rt I CI r I399 H o H39s quot HQ Q 5 H H H 6 quot9 6 H e HO H gt HQC H
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