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Finishing up chapter 6 and starting chapter 7

by: lhall8

Finishing up chapter 6 and starting chapter 7 Chem. 301

Marketplace > Radford University > Chemistry > Chem. 301 > Finishing up chapter 6 and starting chapter 7
Organic Chemistry
Professor Bibeau

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Organic Chemistry
Professor Bibeau
Class Notes
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This 12 page Class Notes was uploaded by lhall8 on Monday October 26, 2015. The Class Notes belongs to Chem. 301 at Radford University taught by Professor Bibeau in Fall 2015. Since its upload, it has received 48 views. For similar materials see Organic Chemistry in Chemistry at Radford University.


Reviews for Finishing up chapter 6 and starting chapter 7


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Date Created: 10/26/15
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quot V 7 1 I 9 w xcicx 3 3 mach C J f L H CHsCH1 Tl 39 39r E quotHi Ha I eryduo enamiarmrs perspectiive farmulas CHj Cm H 3 Bi 39 arr H Br Br39 H CHgCHJ CHRCHE Mm mntiomers Fiszher proiections 65 Br 8 999 pf ge oquot 7yr x o 4 1 I 0 5399 1quot f 59 9 41 ix I Bx V quot 101 A H Y vJ 0 RM 006mm E222 wadge dash q w a quott f 3 v39w fl in r 0 L1 G H a W f 39 r r n 39r 39 V r f a fr I I r l Ir 7 o 7 V 31 I V F E a E a if a I L L is aka Fquot I a I f 5 Lg If I I l 4 l i by he termi al 1 an internal j 1 Br CH3 alkyne 7 alum H a I a I 39 I a I i FHEFHj r CH3CH HCECCHECH3CH3 CHgCHCEggIIZCHEBI HCECH EHl ui aen CH5CECCH2CH CHJCHCECCW 3 4 5 h 7 5 I N 39 f 39 Ithan I bJWM lpentrm SWEZchlmdroctyne FMSmthyl Bhuyne Common nuts4m mm m m 39W39M m VM39m quot not 6 hroma7chlaro4 uctyne not 6bmmo2methyl3hexyne because 2 lt 6 because 1 lt 2 r r 1 wr a m a 1 J I A 1 l J39H quot E K m bf Fm 39 g 2 E r W 39I r r a r V 5 quot r r Fe n r quot 7 A 1 E r 3 r r squot CH1 EH1 T h S 4 3 2 I I 7 2 3 4 5 fquot 7 CH C C r 0514 quot EH 12 quot c 39 Eu 7 I CH3CH5 CHCH2CH2CECH CH2CHCH2CHECECCH3 3 H 39IT Wm ih d ifmm E mai wff gt l pten 1yne 1 hemen5ane m m or not ZheptenGyne natEheptenZyne cm allure IMH he I dim because 1 lt2 because 1 lt 2 CH2CHCHCECCH3 I 39 2 j 1 5 I5 3hutyi1 hexen4yne 5 a p e a 3 F r quot Q E 573 if the longest continuosz chain has carbons but the 3carbon L L It i a I 393quot chain doesno tmntam both functlonal groups therefore the mmmund is named as a hexeny39ne bracause the longest continuous themtentaining both functiona g39rQ39ups has 6 carbgns N H nan 5w 12 37456 654732 I CH3CHCHCECCH3 HCECCHQCHZCHECHE Zhexendiyne 1 hexen5yne not 4phexe n2nyne not 5hexen1syne A J a N i 1 I J a 34 h E W e V 39 K135 all 1 1 Ll MM 5 When the same number is Dbtained for both the double bond gets the lower number prwerimrirhkcao D 0 gt NE gt EEC the ouble bond given priarity over a triple bond nary when there is a tie CHaL Hm 53 I HnCCHe quot104 HCE39CH 34 CH n H 1 eIhane cum ethyl 7 TIEEHFCH 421 CMCHEm 47 CHeCECH 133 CHwECIICH 0 CH ierImagcnzm l Cligi ClI Cl JCIIgcrZCHCIL grimen 5 CH CHE111 quot M r r cuga n m mica CH 6 c 39 39 r z39Pum 139939 I W 39ymum1 Em 2 amquot i Immune Iahnmne Marlyn quotof 139Pmpen39339 I CH1CH33 U 3 m ma5CH riICHmi2 30 camugcnrzcacrr 19 pearsnu lapanm 11th C II cumCH 657 imeHfI I i I CH 515 C h 39mjijlf CH 7 I hexane lrhnem Emmyye JCH2C139IC CF39ICHS CH3 N I cucumcrn 37 Grummanm 2 ds Znhmene 39 Luigi 1 H 7 0H 02 he C39HJ39HCHCZ HN 09 m H2rT CH 55 Mannid MVP Kb 9quot 39 39 39 mmIhuirnr Emlyne 31 r a 3 l j iquot 1 39 a I 39er a L i If 1 39 5 39 9 r r 9 1 1 5 l p r 2 t r gt39 5 f a 39 i 1 I i at 1 1 4 r i l 391 1 i I 1 Ln r 1quot l 5 h quot o 3 1 Iquot rquot H 1639 ii 3 1 11 hi i w w I u p 391 A 739 Ii 39 EH ZZSr law 1 m 7 fr 7 g g X 1 ql 39 4 rr 7 139 lgdi er c in stabiliti s of the trarlsitimi 1 an al kym is less r states is greater than the difference in 1 39 reactive than an alkene stabilities of the reactants 39 a v r z 39quot 7 q 7 r E rr bond rmed i F A EPFP QVT BF a 39 1 wiompiex 139 gquot fi aiicynei FY39ind 39c ffkdmm E i l 7 alkyl cation I E aikyne 7 ahiarl i neislpss if alien39s l li h f a e 1 39 T a 39 Progress of the reactiuzn TI The triple band is composed of a sigma bond and two 7 bonds W 39 A v 1 4 w PM Va 3 r 1 39 v i I J MRIquot v rquot r quotquotw 39 ka quot2 i V quot quot quotquotH t a hwwn w me a u i kg mngpv Q D r 71er Kw L L l i39 39 RCHBCH Hufm RCH CH quotI RCJLEHI 4 Hem Ra ser I Uquot 1 339 9 an alkyl cation quot39 J a vhyli cation H D E s Lid L 1 F g 17 quotamm C 3 C q j a aw 7 a 3 I 4 Addition of an electropmue Addition D fan electropmue a to an alkene to an aikyne V E N L a E H H 6 V 39 L f m m a lm W Qg bggg F QE J1 2E E El E7 W 239 4 V 7 73f sigma ha 2 r m4quot E39l1 C R I u itquotEL quot1 quot39LEL E EP r v f aquot 1 1 r x 1 w H H 394 a E R my F A 39 I 39 I name a secondary a summary a primanu ma pfimmry m Srhmign carbonation viimyth n m urination maria minquot whom 14 Evidence for the formation of a arrcomplex a arcomex Equot CH3C CCH3 t1heelectmphiie 1439 39 adds hefe 2butyne Ha mac 2mm 7 a CH3ETCHCH3 CH3CH2CH3 J H E31 77 i a geminal 3 I 39 I 6 7 H VJ dlhalme h x 1 1 W quotHIE f F 7 x taquot 4 iii x V 7 l L I 939 A L Cquot r W I I a 5 I 739 7 a r rquot I g I g j ff T m 4 i J s 1 3 2 L i g i E 9 i f a 339 7 Lin J si N J U a quotg A u r ff V the electmphile 3 adds here 7 539 v 4 a r CH CH CCEE CHJCHQCECH L HSCHZ CECHE 39 339 3L 39 imam Cl39 2bmmoig 1m V n a halosubstituted alkene f 7i A h u n5 F5 39 Em g x Intimates primary secondary sharing of Larbocjaticn maria 1 LTFEE39J hiD l39le Ix chlka rine tr w Mthdraws RCTH CH3 shares a U1 r mi LH electrons payof z ind actively C1 electrons Hquot added to the mare H39 added in tha less carbon substituted urban 1 quotii w CH CH CCHECH CIiC 11CECCH3 HBr a CH H uchcnj 3 ll 2WD eucgss m a 3quot 239 I39m 11dit oropentam 33ngme m 39 r 391 339 39 r r 39139 v 0 CHICHJCECCHS Ema CHECHE C CCHJ cHz z guineaE I 1 5 m Br 1quot 5 Br 5 r 1 JCH CH ECH mac ITH THE CH3 1 t Br Hr m 31quotquot Equotquotl quotW H v l C mg quot mquot 5 1 I 7 3 W Ni 9 a i fl I 1 in jtvg I the J n 39quotI A En 39 relative reactivity H CHECHg T RCECH gt RCECHE alk ene alky e m withdraws electro s 1 induc yaly Dials substituted al kene This explains why if only cane equivalent cf HCI is used the reaction stops at the halosubstituted al kene r w u E E j CH3cm r39Iztl LCH2m3 gt RC ECH gt 10263 2 CHBCHZC ECCHZCH3 HBr HERVE excess 3 r asymmetrical a 34 15 7 internal alkyme 747 39rmm e 1 I g M V k I f r I a I f N H1In alltlili I a g h iL a m a l I I 1 7 it m w v I 39 V f I I v I r w I L s gt 1 L41 i I L a 3 x a a a d I quot 3991 11 P quot 1i If a w r a g I quotN 39u k a If 52 quot 391 It i u i 1quotquot 39 rJ39i 9 it i f i i 39 t 3 r fquot i 3 3 3 E 1 eierttrophile g iadds here Hgso4 1butene csjcnzcaw PM 35 Emmi an enai i as 7 39 r tit quot t CHgfIHZCECCHECJh H20 2504 a symmetrical Internet arlllyne mics sz H20 2504 339 unsymmetrical Internal atkyne HIE CH ij ECHI 39 r wHg ingL u i Q CHgCEIL CH 4 R35 1Fquot 39CC HID xi P b H e g g gggg g mm Wimted ethane 9BBN 9 barabicyciot3i3JMontana RZBH RZBH should be used with terminal RQBH can be used with internal atkynes 7 LO i I t Reta Hummer r t Laftw i if enol tautamer 9 E quotii i 2 V 7 7 A V 4 1 i r i l I tautominzatmn e i it i39 I aquot E i 1 i i i E r t quot 39 r s quot s quott g I I g g p I l L M I I Ii WE Q H 5 CHJC E 139 ii it H J antral lone 39 quot39 H r Hm CHGriegchHzcn3 CHBCHZCTECH H20 g CH3CH2 TE CHJ CH an anal a ketone Gt CH3 CH3CH2CH3 mica A Because terminal alkyries are less reactive time rate of the reaction is increased with a mercuric ion cataiysta M r 39 r f 1 i r I I 3 i I n K 1 l 3 it I i g i in t a r r m y l 39 d I m r r e if it 0 Ci lg i ifH 311mm r t h i a F t g I a is i L E l IJL39I I I ill I In n w J 39 I I J I 1 t I I I i I I i J I J I i 71 I i 4 K gal 4 i L 1flltwtlikial L I UM H l i I I alkynes 391 l p i a 1 a mu I K E H quotW 79 s r x r r Y ltigt L 39 UH ii I r CH3CHCH CHJCHECH 7 7 an aidehyde 1 H FHrmCH EiEH PM LH3LH2EHCH2 HECHZQH i H alkyne Ik quot CHSC CH2 CH3CCH3 a me alkane a ketone an aitkyne is Kimmieni toan afkane 11 E II 5 F p i 25 a a i 4 31 Temina lalkynes form aldehydesi a 1 T glwr39w I H 639 f L 39 ram wu Internal alkynes form ketones 315 d H g If gt quot 411 3 339 e quot Jquot 39 gquot 2 5 39 iquot quot e r A 1 i F k i a quot i1 i 1 r CH3COO 2Pb2 w gs p H w r 7 r i lead l acetate 39 l additibn has occurred H L CH CH C CCH H CC Kt W1 3 g 2 39 3 2 catalyst w 11 7 2 W CH3CH3 CH3 M 1 i 1 LJLJ L a cis Zpentane quot3i sodium givcs MWquot 93quot me m 39 up ans ec arlf upmsekmnn 31inng I 3 r 7 u Iy 1 I 7 WW H I L i 39m V 156 39 i H 7 I l I 9 L 1 M 39 fruciml fgiwl EC y my cirn we Lmt fiI Z39bmym I 3 H K II 1 VF I f i Iquot g p EH a J r r r I I I 7 j iv ii 7 transsz butene 39 Burkattain E lc a gill r 11 aquot quotI l 1 Fa relative electronegativities of carbon atoms 051 t 39 5 t I h L 1 Iquot 39 a a I i a a 1i i 1P I 1 i 39 H 3 a I u r f r I rubyquot re it 4 Q 3 pa4quot r Q a 4a 551 J L 1 I a new 35quot I J i N If 39 w 7 9 t I r a a 5 C 1 RCECH RCECH NE T amide iOn stronger base I RCEC acetylide inn weaker base weaker acid license acid F quot71 39HJ HH 93 FL w it 2 weaker acid hydraxide anion Weaker base t e CH3 C1H3 ethane puffa gt 60 RCEC39 acetylide anim E130 stronger base 3 sifonger acid f


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