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Class Note for CHEM 3331 with Professor Albright at UH


Class Note for CHEM 3331 with Professor Albright at UH

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This 35 page Class Notes was uploaded by an elite notetaker on Friday February 6, 2015. The Class Notes belongs to a course at University of Houston taught by a professor in Fall. Since its upload, it has received 19 views.

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Date Created: 02/06/15
Milli minions uiiiienes Let s first talk about the kinds of reactions in general 1substitution C Y X gt c x Y 2 addition cc XY gt C C In general alkenes undergo addition reactions They do so in a specific way that is related to their bonding 0 7 bond two loosely held electrons 9 d quotquotC39e phquote 0 weaker than 0 bond 2 good nucleophile 1 cc E N gt W I I carbocation 1 intermediate Ch t 8 39 2 electrophlle aper UC39GOPhlle Less common is C C E H E gt NC gt r c I H avoids carbocation both electrophilic bUt Strained ring and nucleophilic character In each case the alkene s n elctrons act as a Lewis base There are many reactions in this chapter but the same features keep reappearing Chapter 8 A Addition of acids HX 1 overall reaction x H I I C C H39x gt39 C 0 actually we ll see x Cl Br I I I that X can also be a whole lotta other things 2 mechanism there are actually two different ones a ionic addition the most common I l Il Hacifgf CHS ow The ac he Hrs nergy lor ralerdelerr nlnlng Reaction progeess The first step in the reaction mechanism leads directly to orientational preference Markovinkov s rule the hydrogen atom from HX goes to the less substituted end of the alkene The reason for this is as follows There IS only one cation possible when 23dlmelhyJ2bmene ls proxonaled by Her lll H c CH H c 3 3 J I 00 gt c c CH3 Hjc CH3 H36 CH3 m me unsymmemca system H is me more stable carbocexion ma Veads 0 product CHSCHE 35 2912 539 CH gt cH OH I OH 2 1 2 2 C CHSCHZ H3 Hac v i Temary carbocalion CZCH2 more slable H20 u 51 CHDCHQ y DHCH g I 39 HSCiC iCHZ H30 I CH2 4 A m nmary carbocanon less stable b free radical addition this is somewhat more complicted oln general it is not synthetically useful i overall reaction H Br H30 l li Br 1 Ci CH1 I 3C C C 2 F107 OR I H36 a peroxide CH3 The product of anti Markovnikov addition of l liBr ii mechanism smw R R A R Fl chain initiation R 3 R H Er Steps 4 13139 Ficf chain Step4 33 664 E3 33 3 H propagation 6 Recycle to Step 3 and start allover again iii orientation antiMarkovinkov the hydrogen atom gees to the most substituted carbon of an alkene B Addition of HOH hydration of alkenes 1 overall reaction OH H catalyst 0 Note This is exactly opposite to the elimination of water from an alcohol to form an alkene that we saw in the last chapter So WHAT S GOING ON HEREll 2 mechanism exactly opposite to the dehydration reaction to form alkenes Chapter 8 8 An oxonium ion An alcohol 3 orientation MarKVinkov additiOn protohatlo n o CH2 H30 H30 nnore stable ternary tertButyl alcohol cation intermediate C Addition of HOSO3H H2804 and hydration sulfuric acid bSOEQH 6H HO SOE OH H30 H20 0 SC H20 H Ethyl hydrogen sulfate Ethyl alcohol 0 industrial application 0 substitution of H20 prob 8N1 Markovnikov orientation MerCUFiC acetate D Oxymercuration demercuration HgOAc H 0A R g C HgOAc H9OAC2 R x R R 00112 C CH2 c CH2 lt gt C CHZ Hao H k H H mercuratlon H OH2 addition l A mercunnlum on u R HgOAc R HgOAc I deprotonation H 13 ng gt H CII CHZ H30 0 OH n H H OHZ 10 Ring opening by breaking the Initial isolable weaker carbon m ercury bond product 12 demercuration t L39 7 sequence 135 i ONOTE There is the overall addition of H20 in an antiMarkovnikov orientation Chapter 8 11 E hydroboration using BZH6 or BH3THF 1 structure of reagents This srructure cannot be B ZH6 because were are onliy 12 erectrons ava able for bonding in this mollecu e and this formulation requires 14 AND quot39 616 H 39 H H B H 6 electrons electropositive B around B 39K empty P A0 H39s are nucleophilic LEWIS ACID Chapter 8 12 2 overall reaction excellent choice for synthesis BH H BZHG 39i39 I 2 I cc gt C C gt C C B or 2cc I I3 BH3THF H202 39OH H IDH BOH3 lt39 lt 3 mechanism amp orientation 32H6 H BHZ a CC 39c39 or BH3THF H BR HVBRE H BR Dquotquotquotquotc39cquot D 0415 gt ll l3 CHsCHQCHQCllr H D quot D D quot quot D CHBCHBCHQCHZ H CH3CH2CHQCH2 H Transition state Chapters 0 syn addition 13 c c 2 gt ch 0 CH0 HJC 0 anti Markovnikov orientation OH The inniax printch is anothervigonal boron compound notice that we have traded a 87R bond or a BOR bond R repeal 16 R slepsabove 039 two times 0 H H20 A I R 3 RiQH mom RBR B Boric acid 14 4 overall orientation This compound is the product oi overall antielVlarkovnikov CH CH CH3 addition ofwaterto the alkene o 2 CH 0 H30 H30 oH 8H3 CH Hzoz HQ CCH2 gt gt oH cH2 BQH3 H C B CHSCHQ CHZCH3 CH30H2 CHECH2 CH HZC CH Three molecules of alcohol CH3 CH3 A irialkylborane 5 let s compare with hydration DH HOSOZOH l m HBC C CH3 H30 CHBCHg C CH2 Markovnikov addition Cll3CH2 H C OH 3 1 Blls l39 CH CH2 2 HOOH HOquot CHSCHE AntiMarkovnikov addition 15 F Catalytic hydrogenation H2 CC Pt Pd Ni surfaces Using or Rh Ru organometallic complexes H9 00 No reaction H3 C C n C C PdIC I lnsoluble H H heterogeneous catalysis H 020 2 p C C RhCIPhsP3 l I Wilkinson s catalyst H H Soluble P Q homogeneous catalysis Chapter 8 16 stereochemistry at surfaces syn addition ID D 2 550 4 c Pro2 c CH3 CH H30 H30 945 cis Adsorbed Adsorhed Detached hydrogen alkene alkane I quotC V HrCg 71H V I H i c Metal surface 39NEta Maize Chapter 8 17 G addition of carbenes and carbenoids II 6 CH2l2 ZnCu Ionl2an CH2 carbenoid Simmons Smith reagent 23239 CHZIZ gt Zn CuCl Chapter 8 18 filled lone pair Carbenes Lewis base six electrons around carbon empty p A0 Lewis acid H I H I E H C 2ccquot LeWIs base I I1 H 2 C c c 19 H Addition of halogens 1 overall reaction X2 Ill39 I c c rgtgtlt ogtlt xCIBrI 2 mechanism cyclic bromonium ion 7 Br Br Br rquot gt c I Br note relationship to the addition of carbenes Chapter 8 0 net stereochemistry then is trans addition trans1 Vz Dibrcmo cyclopentan e 3 halohydrin formation very related reaction Br c k CCIA I Br Br Br I i i c c o c c c 2 1 i Br Br Er oH 012 i c c J J c39 c CHJOH I i i c c C OCHS hapter s 21 The general case I A chloronlum Ian A specmc exampka deprotonation deprotonallon Cha pter 8 22 l Epoxidation 1 normal reagents 0 l l Rc6H F CCb39H H o H a Hydrogen oxide A carboxylic acid Tri uoroacetic acid water i C H c u H R 9Q FSC 9Q H o H Hydrogen peroxide A peracid Trifluoroperacetic acid normally R Ph or 2 overall reaction CI 0 Iquot u I 39CC39 COOH 7c 39 Cl MCPBA I C OH Chapter8 23 Cl 3 mechanism E C quotWEI 8 w a C C Chapter 8 o 0 G Am H 9 c o 390 quot He 09 epoxide An oxirane CFS oxacyclopmpane 24 4 Ste reocherl istry The general case cis Alkene Howlsquot u CQWH R Cis Epoxids CFECOOH cis Epoxide A s sclIic exam la Chapter 8 KrarIs Epoxide 5 synthetic uses of epoxides H20 1quot H30 i HD 0 Z 5 1 H H20 1H9 30H I u n An epoxide A 12 Womanglycol The mechanism of epoxide opening in base H H 0 39 393 0 Ho 5 5 8N2 protonation p H9 YQH gH QH The mechanism of epoxide opening in acid H 5H2 H HO HQ 0 protonation 0 8N2 deprotonarion gt gt gt H30 A H20 A 939 H H 9H H25 H25 Chapter 8 26 J syn hydroxylation with 0304 or KMnO4 1 overall reaction OH OH o 0 OS H202 0504 or cc gt O O gt Na2303H20 oMno M O 39 cc it 0 O gt cc HZOI39OH Chapter 8 27 2 mechanism o K 52 0 O K 0 b39 Mnlt Mn 2mg 0 d 9 U 2 9 J o S forget about 2n step 390 o O O 00 C CE 00 p C C A cyclic osmate ester 3 stereochemlstry General cases 0 b 6 6 Mn K H6 cSH Qs quot Hb39 b39H 6 H25 5 b39 H20 39 T C C Mn02 39 gt c c H20504 xc c QH M32503 I 12 Glycol I 12Glycol Not isolated Can be isolated but often is not Specific examples H9 KMnO4 HO 0304 H20 gt gt gt CHSOHHZO C Nazsog NaOH2o c HO o 0203 H0 85 96 81 H KMno4 I R 4 a problem or two a Os is the most expensive element b KMnO4 oxidation goes too far 0 9H 9H Jk R C C H gt R R KMnO4 n o R39JkH gt KM n04 H Ozonolysis CC 1 overall reaction 0 0 2co 03 c o MeZS Chapter 8 29 2 mechanism A forward 13 di polar addition reaction A reverse 1 S dipolar addition reaction A s eco nd forward 13 dipoiar addition reaction Chapter 8 30 3 synthetic uses General mes Speci c examples W u I Summary 1 Alkyl halides gt Hx H x Allure highly substituted halide is formed Nlarkcvnlkov addltlon x Br cl or I 3r Alkylboranes 4 Alcohols E Haw H also conC EH H0 HZSO4 add More highly Substituted alcohol is formed Nlarkovnikov addl on H 8H2 repeat 3 3H2 OH H20 3 H0 The number of hydroboratlons depends on he bulk 01 the Less highly subsl uled alcohol is lorrnEd alkene boron becomes anachsd to the less subslltuted antklvlarkovnlkov addltion end of the alksne Cha pter 8 32 2V Alkanes R R H F t C 0 g R cl Iv cl IR2 R R 4 AICDI IQIS F F 39T T 1 H 0A 2 C C Q C R C C I 2 NaBH 1 R R HO H CH Markovnikov additior L no rearrangements 5 Aldehyde R cc H n 1 03 2 CH S 2 C O r 3 2 H Chapter 8 6V Bromo alcohols and chloro alcohols R R R X CZC RC39J3R also straight R R HM addition of X2 anti Addition X Br or Cl 8 Cyclopropanes R R CH2 oio CH2N2 R o oR h39 or A R R R R cis Addition for singlet carbene but both cis and trans addition for triplet carbene 13 Oxiranes epoxides R R o C FECOOOH R R C l quotEC Cs R R R R syn Addition Chapter 8 34 11 I 2Gycos R R T T 00 R C C R 2H20 I I R R NazSO HO OH synAddmon H R R R tKMnO cc gt H C C R Z HZOHO l I H R HO OH synAdd39nion R 0H 0 HOMO Rc cR 4 i R g C R H R H0 R annAdd ion 0 H OH R R H0Ho 7C C gt R II T R R R H0 H anIiAdduion Know all 0 the mechanisms we covered in this chapter Chapter 8 35


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