4 nk Dritial Concpls & Reveur Problens v ; Organic Chem Alcohols / ethers / Chis /sulfides le OL Name tg: Bea dbeucteres OH a. 6) ; Coad preseryctive) 2H (menthol) : flavoe B- 2 4 ret @) tis — 2-Usobu: cyclohexanol § trons ~3- chloro eyclopentanol & 4 ~phengh— 1,5 — —heranediol 2, Shou the reaction 4 crc -molecale prom pro sblems tothe KG Oy oxide zing reagent, Showd Be nat tarrick produc § no, action” may. he a gessbee 5 ans, Sor diols. eat both, alcohat gecge A Sheu the reaction of tack, tolecale proms problem, */ (with. He S04 tebalys€ aa & debe dara ton reagent, Shaw both products 4 pick major product cf there. (OS one, Ser the diols, two ene | apply the reaction to bath, akcohst Cisne wantion’ meg be a possible anstsas) | (Orly Ewe products par the Lidls since one y the | alenhols cen produce only ss pocsithe foulke bond)2@ Ou koa YOK 2,6 dhe - ene -butyd - 4-metigh- 3 se sphenoh &. tod 2-tsopropye — t- methyl eqclohexanoL 8 -broimo - S~(S -Lsepropykegeloher ye)~ Alo ~ dimethek ~3-nonanok S— propyl LA octaneddok OW 2) oH £) g) HOLA Crk , s 8 a ee 2a) no reaction - b) K.Cr, O4 : weet Lo ‘ OH ™~ 8. j K2Cr0. Q! ~ a OH ~Y 4) te Keng Sot HO A| © | He pH © no stereacher.! Me fe eso, Oye * 2H ee Oo + 8 a ce ORD oO He so, ® ® wtP i we 280 ® Zo . a 1 OA? pL ALLS QPEL Strplet tyclopentyl Replyk ether systematic: I> cyclopentonsheptone Cor heptorg eyclopentane) 1 ha, by, PS Ay S-chloro#~ proporg ~ 1,-octaduene O Oke hig 2 , Hoehlore -®-athye-8- 1 ® T heptanethcok bo ONAL batys phenyh suri, Sa). “NON moderati: poloee on = strong Lipol: wv Rayhrogen bonding hegher 8. P * shong dipole w H- Gonding mech etm ane mora 6) NN ont ¥ Hagler ®.PY both “hans Sea | on force 44008 | When. molecates hae Sout fare types Highr MM “hig BP 8 oe strong dipole w H bonding Oesu = moderate Aipole@ OH Lo Ce ‘\ stereochemestieg. 2.2) Kke0y ho. longer ey wn meet, puny \( teigonal planar () i Keno, “ 3. &) hovulin 6) He H, 2804 gs « b H SN OH (ase neigh boeing HS ave Shown) ~ Mat aS imap. Ogee He Ha 5 et 30, © DO maj RL 8s CON SLE + oR OL no storeschent Ceigel iplanor ( H2S0q | b) eS majo be | on ruleas qeven.@ 1 Nene a) Drone C name by single method : 9 schematic metho) a “ by, wa-r 9 “yh me SH a) cero Cstmpte me that!) S. Whack, gf te ftw0 Congouende has higher hocking Poca 4) re BW oy 2 Coot * Same Mam) by Sok ge OH t (erg Actforenk 4) Sy crn" on Ousa s lboth x Same Mm) b. Fou a,b Fe from problems, aeleck ihcch, % Hee theo Compounds is more doluble in water, 4.) Draw tee dteccture $ name the 2fher formed 3~ pentansd plaw |~ brome butane (in baele solution) b) Gear steuckwes | ndme the three others whic con ~ he foemel en a Solution A Q~ prath ethane tort (= butenet Cplua aecd catty st) *Gemple sq stem) 2, Shao a two slep Syntheais (2 reactors) fr, Leck 2 2. 3 2.8 a SS SN by Hats cH, —* CHy¢~0H gre an a om ag® bie hen beet solability s-matok, force types (See *s) Hao = yn, = steong dipole uy tg drogen boading BOK matches N20 the beaut ~ more soluble “Sou fee less non-met che tg deoescecn portion has ts move soluble us BOB “) cr matches HeO the beet = more soluble © @, si! 2 4 @ 14 oS o2e2@ > Aho eo a XR 8 + OH © . 6 <0 an butory pentane bye OAD Oy , lL dink a= Cagle inteye ethyl) ether umrou | Cr@ ONAN boxy 2 ~egle pentyeethire ether Q+® ON . dhbutyt ether : ‘ OH : ea ee HS UL ete, RL : + iy Heacn, HEE? pe crkou HO Toy 3504 i Ho eyo Gee TY pe 4 vA et AA Be abo : Y tee OG 7 Ts,