Miey (fab ce por Oler er OF 1. Give the principal organic products for the following reactions. ° AA LDAcse * OC 4.1 equivalent LDA Le ¢ ene brre 2 Se sai kaill WD \ Joh clenince an V Nhe Gronede —E b. Oo . (E HT equivalent RS) HO’ OHMOBE ' ° Be on We Je a © ea ioe - my os ITE Cc C9 1, 2 equivalents S ow (Crstgo) WA ( ‘OFt co mo TET \ “» ce 2.H20 cy “ Ne No, NH2 _ on Se rE Nucleo@v s\ve ave vane Subsh Wher1. (continued) Give the principal organic products for the following reactions. aN \ of L \ ' ° 1,.LDA rN > 4 . 2 Br 7 { — , Gbr 3.H,0 9. or a Yl h. 9 ‘excess Et(OH/H* va ( 7 ——— o O tBuNHa/H* cy kets i 1. NaNH, Y —— Ne = ar S< /\é wo 3. HzO, pH72. For the following pairs of reactants identify the ELECTROPHILIC and NUCLEOPHILIC components and the identity of the product. Note, the actual nucleophile and electrophile may be an intermediate that is formed after reaction with the reagents shown in step 1 of each fenstorman «a (Qu) a Mi 2 © o~ gt er Wr ae 3.H20, pH7 al 4. NaOH b. o 2.0, 3. HO, pH73. When naphthalene is treated with Cl, in the presence of FeCl, the major product from the reaction is product A and the minor product is B. Using the mechanism of electrophilic aromatic substitution EXPLAIN the product outcome. Your answer must include a detailed stepwise mechanism and a discussion of the stability of the intermediates formed in the reaction. The carbon framework of naphthalene is predrawn to save you time you just need to add the chlorine substituent, the double bonds and the charge. Fecl 4 eee a. aca . cl ZN QV “CO CO ® o complex 8 ay sh io c = cy CY) CE 7 @ ed for A Two Wee o complex . Cea cantata tte Oeomglex C) preverve arowahe ebb Nigaten A one Othe (woo mos \n cons Gor B. ovoualeerty is only prosreed Ga AD} S veronrnce shrrcianes. vod will be han more skeble O- complex 30 A TEaL Gros huis Keel enerat waitermedi obs4. Write the complete stepwise mechanism for the following reactions. Show all electron flow with arrows and include all intermediate stuctures. ar a ‘ot HO ~_OH fr a O dehydrating agent to remove HzO O Hilo fr. HO 4 oye ow orl \ es ¢ id Heo PV o ROLE AL 0m ——+ — -40 (@ rm 7 (2 0. ow Ly °. ° . cS — ca = fe} 1. Excess, OH b. ¢ Figen ov ‘OEt ( 2. HO, pH 7 \ Ze Wo \ om Oo © 2 Cp ae" aa er}sheps ere jul the reugsedt ‘wane Pemaod 4. continued Oo @ RB Briers i Mechanism must account for formation of meta-substitued NO» product. eg RB Cas TR, Z ip — 6 — . ra ax na So oe Subsviubon O of @ be N82 yan veroarnce Swuckinss UL heck +u0e Of S complex is on adveceul alom . @ KR on sce canaol conibute lo Ire shobilily HeY com p\eX4, continued ee 1.PhgP + a= e. 2. nBuLi Br 2 3. | (oc oem, gi oF PPh om es \/BO 3 wn core —}cr ey eh x at |— f% ez = Cre teien H = co + PhiP=O 1. NaNH2 | 4 WO: On OG, —- Oar5.Design syntheses of compounds a, b and c. The pool of carbon-containing starting materials that you can use are shown in the square brackets, You may use any other common reagents. a b. OH c. Oo 7 Te V o Santlesi, « Grignard Yea 2 Me? MB, Boas Ss es on Na 26294 aa Was,