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by: Malcolm Glover


Malcolm Glover
GPA 3.85


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Class Notes
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This 37 page Class Notes was uploaded by Malcolm Glover on Tuesday October 13, 2015. The Class Notes belongs to CHEM 2060 at Louisiana State University taught by Staff in Fall. Since its upload, it has received 43 views. For similar materials see /class/223111/chem-2060-louisiana-state-university in Chemistry at Louisiana State University.




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Date Created: 10/13/15
AlkeneIAlkyne Reactions ADDITION amp ELIMINATION Hydration amp dehydration examples of addition and elimination reactions involving alkenes in previous chapter ADDITION REACTIONS Add39n Name Mechanism HquotXquot hydrohalogenation electrophilic addition quotX2quot halogenation electrophilic addition HOH hydration electrophilic addition H hydrogenation addition I I i 6me NIoINIo Al 1 82692 IOIIO Al IOI 90m m 628 0 Al L L 2on m m I 628 O I m N N 2on A 0 Iolo I Some Electrophilic Addition Mechanisms V EHz CHZ inf gtH23 3H2 H V HCI H H2C CH2 HT O gt H U H C CH2 0H2 gtH2c3 CH2 2 HZC iDBr l r gt m HZCX CH2 Br gt HZC CIEH2 o o I I Br Br Br Br omonium ion Bridging ion occurs with chlorine too Bromonium or chloronium ion hogs all of the space on one side of both carbons Forces bromide anion to approach from opposite side of double bond What difference does this make Often cannot tell from product that bromonium ion intermediate was formed Sometimes you can tell however Example cyclohexane reacting with bromine next page Br Trans addition to double bond makes trans product diequatorial What about addition reactions which don39t form bridged cations When a carbocation is formed as an intermediate which of the two doublebond carbons gets the stick and which is stuck with the charge carbocation H HBr gt H3C CH2 CH CH2 H3C CH2 CHZCH2 39239 H HBr POSSIBLE PRODUCTS H Br Br H H3C CH2 CH CH2 H3C CH2 CH CH2 This product is major product Why is this Markovnikov39s Rule Carbocations like to have lots of carbons around them just like double bond carbons do Carbons are usually very social atoms They like to be attached to other carbons especially if they are slightly unstable double or triple bonds or very unstable carbon intermediates Exception Carbanions are the antisocial beings of the carbon world They don39t like having carbons bonded to M Exception to this exception All carbon atoms including carbanions like to be bonded to double bonds or benzene rings Double bonds will be discussed later in this chapter in Sections 54 and 55 on Resonance Stabilization of Reactive Intermediati Benzene rings will be discussed later in the course A good way to sum up stability rules for carbon species is this Carbanions are antisocial They don39t like to live next to other carbons All other carbons are social They like having other carbons around them especially if they are unhappy unstable because they don39t have their four sticks or are part of double or triple bonds and have accessible electrons vulnerable to attack by predatory acids It makes reactive carbons feel safer to have neighbors except antisocial carbanions Double bonds and benzene rings are the movie stars of the carbon world Everybody likes having them next door m antisocial carbanions Iw 01on E0 0 01w 1 r Oltm OgtNwOZ Oltm OgtNwOZ Oltm OgtNwOZ Imlt O mltmm 992 mm UOZ OEOltltU ltm ltgtZ Skip Section 52 Addition Polymers Addition polymers are created by reacting certain alkenes with either Lewis acids create carbocations or peroxides create quot radicalsquot If a very small amount of acid is reacted with some pure alkene usually called the monomer molecule then a carbocation is formed as discussed previously If there is such a small amount of acid around that the carbocation can39t nd the anion which came from the acid then it will give up trying to nd eyeballs and settle for reacting with another double bond on another monomer alkene molecule instead This will create a new carbocation with twice as many carbons in the molecule as the original carbocation The larger carbocation will hunt for eyeballs again and probably have to settle for reacting with another alkene monomer making a still larger carbocation etc Eventually a carbocation will get lucky and nd an anion with eyeballs to bond to making a large neutral polymer molecule but by this time a really big molecule will have been created The same process happens with alkenes and per oxide quot catalystsquot except that intermediates are radicals cyclops mDOmOgt Om gtltmm A OmA OFm Al OmA m IO N A olxooof POLYMER ETC H3c j 393 CH3 gt 3 b 3 CH3 2 39J CH3 Allylic Intermediates H2coH CH2 lt gt HZC CHCH HZCCH 39oH239 lt gt H239o CHCH H2coH oH2 lt gt H2C CHZCH Carbon says It ain39t so bad having only three sticks if I can share my misery with my neighbor INOHOIIOIN Qltm ltm gtrxmzm IonOIIOIN oltm ltm EAsz INoHOIIOIN oltm ltm EAsz INoHOIIOIHOIN ltm ltm ltONm ELAsz When two alkene groups are neighbors although they are safer more stable than if they are alone strong Lewis acids and peroxides can still prey on their electrons Since neighboring alkenes can share their misfortune when one of them gets attacked and winds up with a carbocation or radical carbon reagents which normally add atoms to each of two carbon atoms in an alkene can instead add one atom to a carbon in one alkene and the other atom to a carbon in the neighboring alkene This kind of reaction is known as 14 addition to a pair of neighboring double bonds 14 addition adds atoms to the first and fourth carbons destroys one double bond and moves the other double bond to the position between the second and third carbons in the 4 carbon chain mfal HZC CH CHCH2 CI EZCCH CH C H2lt C HZ CHZCH C H2 Wm HZC 39 39CCH CH2 CI39 H HZC CHZCH CHZ CI HzC CH CHCH2IIIO2 gt g 12 12 CHz CHLCH H2 H2c CH CHCH2 HZC CHZCH CHZ CHz CHZCH CH2 0 notice two 4carbon units connected with double bond I between second and third CH3 carbon of each unit r ETQ ETC peroxides or Lewis acids HZCZC CHZCH2 r l 14 additions CH3 quotisoprenequot H3C eCH CHTCHeCH CH7ETC CH3 CH3 RUBBER Vulcanization Natural rubber has double bonds at every fth carbon atom in the polymer Sulfur reacts with some of these double bonds in a freeradical process and thereby links together many different rubber molecules into a massive 3D network turning rubber objects large enough to hold in your hand into single humongous supermolecules Ozonolysis A way of breaking alkenes down into smaller simpler molecules which are sometimes easier to analyze CH3 CCH CH2 CH3 gt 00 OCH CH2 CH3 Dr aw molecule with double bonds erase double bonds and replace each double bond with two carbonyls O 0 ll H3C C CH3 and H C H are ozonolysis products of what alkene To solve these face the carbonyl oxygens toward each other erase the oxygens and double bonds and replace with a single carboncarbon double bond Homework 5390 What alkene gives ozonolysis products below ICI H C CH2 CH2 C H 2 CHgCCH3 0 O SKIP SECTION 58 Carbohydrates OMIT 144 GENERAL Biomolecules all perform multiple functions in the body Most of these functions can be viewed as being either architectural or energyr elated Although all four major classes of biomolecules covered in next four chapters of text have functions fitting into both of these broad categories largest quantity of carbohydrates used for energy storage Blood glucose and glycogen in liver and muscles are carbs Read about Type I and Type II diabetes text p 410 Carbohydrates invented by prokaryotes as energy storage molecules a couple billion years ago Empirical formulae of simple sugars CnH20n Carbo carbon and hydrate water Complex carbohydrates formed from simple sugars by dehydration loss of one water molecule for every sugar sugar bond formed Empirical formula CnHZOm where nm number of sugarsugar bonds Carbohydrates are partially oxidized hydrocarbons carbon and water Burn colder biochemically than hydrocarbons would more controllable CARBOHYDRATES MONOSACCHARIDESOPEN CHAIN Monosaccharides all have 1 site of unsatur ation CHZOI1 empirical formula Have either one carbonyl or one ring Aldoses and ketoses Monosacchar ides either aldoses or ketoses In openchain form Fischer projection Moses have ehyde on one end and CH 2OH on other Aldehyde drawn on northernmost end of Fischer projection CH 2OH on south side of Fischer projection Moses have ketone carbonyl group somewhere in middle of Fischer projection Have CHZOH on both north and south ends Ketone is placed as far north as possible in Fischer projection CH0 CHZOH HO OH OH O OH HO CHZOH OH 5carbon aldose aldopentose HO CHZOH 7carbon ketose ketoheptose D and L sugars IfOH group on rst crossbar from bottom in Fischer points right east sugar is a D dextroright sugar If it points left sugar is L levolcft sugar Numbering Northernmost carbon numbered quot 1quot and southernmost carbon has highest number Number from top down CH0 CH2OH HO OH OH 0 OH HO CHZOH OH a Daldopentose Ho CHzOH an Lketoheptose MONO SACCHARIDESHAWORTH STRUCTURES A monosaccharide molecule can form a cyclic hemiacctal or hcmikctal with self reaction between carbonyl and one of its alcohol OH groups To generate cyclic structure from Fischer projection use following system 1 Number the Fischer structure top down 2 Make ring by attacking carbonyl C with the alcohol 0 which makes correct ring size count 3 Draw ring so that included 0 is either due due north odd ring size or on northeast side even ring size of Haworth structure 4 Draw updown bonds to ring C39s 5 Number ring carbons so that anomeric C was carbonyl carbon in Fischer is on due east side of Haworth Number clockwise around ring most sensible convention 6 Attach OH groups to ring carbons m in Fischer is Q in Haworth and vice versa Mnemonic read from left to right and up to down 7 Reverse convention for carbon just left of ring oxygen in Haworth structure This is C bearing 0 which attacked carbonyl carbon in Fischer If carbonyl was attacked by CH 2OH this won39t matter carbon not chiralcontains two H39s in Haworth Otherwise locate the E on this carbon in Fischer and place with opposite convention in Haworth can39t place OH it39s now gone 0 attached to anomeric carbon 8 Locate OH on anomeric C according to whether you want on or B The on and 3 convention is determined by the highestnumbered chiral carbon in the ring on means OH on this C was originally on same side of Fischer projection as the OH produced from carbonyl oxygen 9 Locate all other groups attached to ring carbons so as to conserve original Fischer chirality 10 For carbons attached to anomeric carbon or ringclosing carbon look to see whether remainder of Fischer projection ows in same direction up or down away from these carbons as original Fischer projection If so use original Fischer projection otherwise reverse OH positions EXAMPLES CH20H CHO OH OH OH HO 0 OH HO OH OH CHZOH OH Make 6membered ring alpha anomer HO CHZOH Make 5membered ring beta anomer To reverse this procedure 1 Number C s in Haworth structure Any C s attached to anomeric C east of O which outside of ring get lowest numbers Number until you hit anomeric C then go clockwise C39s attached to west of O reversed carbon get highest numbers 2 Now set up Fischer projection numbered top down and put ring OH39s into correct positions according to convention upleft downright Remember to invert chir ality for westside C 3 To specify a Haworth structure as aldopentose ketohexose etc fir st look at number of anomeric C east side of 0 If number1 then aldose otherwise ketose M of sugar is m of C39s including C39s attached to anomeric and ringclosure carbons east amp west side of O in Haworth projection POLYSACCHARIDES Glycosidic link occurs by removal of water from two OH groups attached to two Haworth sugar structures To determine designation of link ie oc14 number the connected Haworth structures to determine numbers of carbons linked together by oxygen bridge Write down these numbers and place on or B in front of whichever number s isare anomeric carbons Remember on or 3 refer m to anomeric carbonsnothing else Now generate link designation using following examples Oil 32 becomes 0cB12 ocl a2 becomes ococ12 ocl 4 becomes oc14 1 B4 becomes B41 Common Polysacchar ides NAME LINK BRANCH FOUND amylose oc14 none starch amylopectin a 14 ac 16 star ch glycogen a 14 a16 liver cellulose 3 14 none plants Skip discussion of nitrocellulose and rayon p 428 Read section on blood types on bottom of page 430 in text


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