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Exam 1 Study Guide (Montague-Smith Fall 2015)

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by: Carianne Powers

Exam 1 Study Guide (Montague-Smith Fall 2015) CHEM241

Marketplace > University of Maryland > Chemistry > CHEM241 > Exam 1 Study Guide Montague Smith Fall 2015
Carianne Powers
GPA 3.4
Organic Chemistry 2
Dr. Montague-Smith

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About this Document

Included topics were taken directly from Dr. Montague-Smith's Exam 1 preview sheet that he provided through ELMS. Good luck!
Organic Chemistry 2
Dr. Montague-Smith
Study Guide
50 ?




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This 21 page Study Guide was uploaded by Carianne Powers on Monday September 28, 2015. The Study Guide belongs to CHEM241 at University of Maryland taught by Dr. Montague-Smith in Summer 2015. Since its upload, it has received 277 views. For similar materials see Organic Chemistry 2 in Chemistry at University of Maryland.


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Date Created: 09/28/15
CHEM241 Exam 1 Study Guide Based off of the Exam 1 preview sheet provided by Dr MontagueSmith Mechanism List Dkes Ader rm Glow adder vxn WI 0 diene d xenwn39 e DSSECJ der W H a fa J a 0 lt u 5 O H I buadiene emwene Pms m is under neHa conkm and has 0 high acaava on enerqv H 03L 0 sveed Mags up 032 lll 6w p nq C N cN ED e I E cis A 39j 1 9 5 C acN dona nq CEN T r5er cis CN 5 6 CN 39 j a T K emn domers mus be S39C tS fut CH3 39uns39ude groups up 0uslde groups down Electrophilic Aromatic Substitution Fwsr damnime t3 Nomadic O b flT bonds CCC i pmmr 9g atoms 39m r39tna Ltml b 9 n WM 09 SYQ 0V 5 SoNe 40F n 39 Ltn Z rune it n meqer mm 39 Mtius the me Q MmdiM E Q A O mq om h no S bung pomov wwSkar dmm 011 L gaps A make elecmpmte Q h ottuck en Equot tom carbon H E E Q a stabmze b resonance hm LB dem renorte 0 vecwer ammoc c r39mq codmwh39c Gene r39uc Mechan39tsm form eecvophtte 99 4206 EXK K n 096004 i 9 fShovxrgt L devote on 2 1 9 a tau 9 gt2 gt G Bromonation Br 96 FeBr3 assume momsfrm on Mechorixsm L make etectmpvide 9 e 2r P3fr aFePar3 Br Br FeBr3 BAD 2 TI oMuck quot a lt9 e 4 Br 9 U159 Par FeBrB F2 Ba good emflng group 9 3 smbmze by momma H H Br 6 H J H WH far 9 G LL depm reha re 9 Br Fe 5g Base Nitration O H No f l HNOS ul Mechan39xsm l make aecwbpmm Ox 0 e O O HOSF39OH 4 o cg LEE 6 quot 1 Sea WNW O 2 quotfr a ocK H r 3 ya N20 II O1 9 9 3 sm deaQ by 030 name X A a lt9 9 o N50 W D 09 9 09 09 1 depvo ren Me Sulfonation O FUMI39W u e W oe a 303 v 0 H30 I b E 30 7 505 QM Meohamsm make ELECHDPMC n W HO OH HO S OH TL Jam39s anhydrous and o o ream wm cs wa rer e B HO Q Hzo D O l O AZSO k 20 H20 3 stur o lid dealWNW 2 IT oHocK it 0 1 depro mnade 5 esononce TLC ShOW OK YQSORQ WCQ I e 30va an he exam S O Desulfonation e S03 HgOGD gt A G L H Ollz Essentially in desulfonation you are using the 6 So 3 electrophile to remove a pi bond and create a G H positive charge on the ring The 803 will then stabilize the ring by detaching itself using the d negative charge on the third oxygen FiedeICrafts Alkylation R Cl 1 a Q p403 Mechamgm meze emampMe 43 e B R Q quotA C 3 9 R C AC3 a R mam CarbO IC a on cutkrbphne 9 21V a oack zmvmm3 Wdeprmenu 9 NR H R K HClACl O 9 3 f 3 resonance FriedeICrafts Acylation 3 0 RgCl AC3 2 H20 Acyl Meohm sm I make emcmpnile quot ACs Ci 6 9 9 R gEV a R C C AlCl3 9 R CEO ACL lJ acy um ion L G39 dedmph39de 2 TV Mack R czo 9 CW 6 Raepwkm re 0 A03 I gt n H O 8R H C Z 0 aresonance H30 0 OMIT Directing Effects 2 All carbons equal 3K EUT Vxer s an a achmm Br Br 39 03 Fumm 5 onhon HQSOL Br orJrho 4 para W5 0H7quot 0 Pomquot mea 4 5 quot 3039 Br mm so3u N01 0 L 0 E Directing Effects con39t 5 I E O 0 0 HOW 5 V E 0 vs M ae 93 mam1mm posi fNe quot one poixr ANbloR charge adgocem 0 r39mq neqowe charge 0 0039 new 0 r39 n N 5 l g Y 09 I M1 36 i Mechamsm O P Uwedwon 60 6 oatk3 OCH2 OC 3 i e gt i more 395ka df fa Q lower AE 1 JEmcher rxn J ocaj 600 OCH3 E 2 6 more reSbnance lt gt FOYI TS i BUT mew 60 00 00H OCH a 5 2 Mew 39bxredion 90 Gquot O C90ICIDO QOEID O QO O e lt5 4 g 6 H i 2 a G 3 IN CO NWRST 0 c9 c9 o o a 1 3397 i i0 i i 2 v 019 Radios OCH pro dud nixhare 4 9 powou usunutg vredom modes NomaM pom 393 oero ooPn occur BUT 5 oanr nq ese pud b0h pvoduc rs down 2 O gt omus mm a Ac vo ion IS Deach uo on 2 6 A 9 deud gtgtgtgtl D j e mdu ltltltlt 0 directors exeepi Hodogens Acmo on M o39 ecors AND 14voqu Deac va on Mm ple Subs r uens M N01 N02 19 an 30 H 04 2 L1 739 39 2 N 7 R unog 7 OZ HMO CH3 A CH3 A 0 cogH cooH 733 e v 7 COOH 3 Br cooll 0 OH oocmmped Z 9 N02 TM A las Few rxn NR NO 2 1 5m 3 HO 273 NQOH HZ mo2 ozN N02 cu3 OH OH 2 O noz Noz 2 mmna U kvgk I z w P No VmW 1s 0 6 w Xmmwlt mzu Cl LT 69 6 Ammoa39wc and a 69 deove Jena Q mos soooe 9 O OH O now 6 H nvxceo3 quot lt LG 9 NU W W 4gt W Fa 6N1 0Tc5 0 W 09 W NZ OTcS 2 L l 1 E7 o 90a oa Benzylic Radical Addition Br rN VXI gr 9 23 l G39I39HOCHOH my ET 8 W p Q Br f BF 5 Br Z propaqo onB gr LEV e BrBr 3 Ammunition H BF H AM a e r 9 2 5 H H UNSTABLE H BeS r option 1 quot7 V 9 9 w ow CarboCodion C 3 Br Br nv FAsT O e a esonomce Roes oplaon chromaHQ O N Br N Emmosuccimmme N ll gr m ROOR O Nucleophilic Aromatic Substitution NAS Medxamsm F Nu FM E2 a 2 H QM La 939 C3NO N 06 N O F Me isienhdw Comm k v Phenols R A on OH OH Doesn39t behave like a normal alcohol J O 02 N02 06 Phenols are great nucleophiles for 8N2 rxnsl gt 2 9 esonomce loans 8 N02 lcric acid Phenmole 2le 9 0H 0 R Ma Q 2 R All 0H 0 0 Quimone l COOH ll 5 o 1 KM Ol Ol39 Toms Vquot N KMan 3K0 2 lb 40210 1gtlltoL l


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