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Chapter 12 (Aldehyde Ketone and Carboxylic Acid)

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68 views37 pages

Chapter 12 (Aldehyde Ketone and Carboxylic Acid)

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Om Shrivastava
Copyright
© © All Rights Reserved
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CA+ 12 i Date A A Getonl anfroucon) 7 KR alldohyets Ketoru. Paap Conborqlic {Wor ___fig v_ AN Ch Sig [are oa a2 Y=0_ ey, Sey Ny Oy _Ciycho __cigcomis nena. CAswoy OO ie re - c =n Wa — c= cy bed =a ttn z a4 Cc OH Fretaldslydo _ Arahans. Formaldalyb- Fake acid #4 Jf 8 [>on 1 ~ H+ oe OER il c= ce] Eo [Oa GPx Ccl/Br] T) ae co} wW ee? Ce & pc-Ch — OC = EN = B Bwmebyhraldahyd, \ =ul= 3 tome bukanal 2 | | evi — C= CMa cN: o il Acetone Propan- Q-ona wy Tu r a Obs CNS Axeto phonsrs_ pRe 0 = 1- Phony| ethan-|- ene + TESS oO 4} : eh > NoZ 3 CN: =) Paopio phonono— oO ti EU = 1 Phenyl propan- 1-one [Zia CaN Benao phenene_ Sa ~ SO = Ait -Siphony| methan - \rons Cig-e-W ON: = Arteta) hyde, a mu = Ethanal. or ethan-l-q|- - ° ! J “Cg Ca- CH CN = Propional dahil - urs prpanal ~ has Ns _P_ 1 ts = Cry SH =O = Sha . yaa a - — ____4-bnmo= rail ep ana ' _ OC = 4 = O1= oy s 4 3 * a Pent-a-en-}-a] or Pent-a-enal ore cyclohanane Canbal dabyda, ae 3- mathyl cuclo pemtanans “09 FI _g,y=Bimathglperrtan 32h Chom =e =e . 4 te : # Canc fy anal : = —c- Ci - oxbpentang __ is 4 : a a+ : 7 3—a—_t ; comb alde —~__OHC=cy, —CH_— CHa - CHO Prrpane —112/3~ toi carb aldthgte / at : _ cuo — rose No. [_] AF : — = _€ Hewo.C = Formaldehydo— - - - = = methana) = - = —— — = CAyCHO CN: = Arataldahy da ae i “oO: = &thanal ma _ ae Gra)gcH CHO => C= CH= CHO CN = Jobubpaldal yy ur =a uty Cgc Gers) CHO D CHy-C CHO_ CN. = A Matheney T , beg Prpiongldys \| Dux Mutiny Propand ROEHL HD TN: =Naleraldshyds_ a-u? = pentanal : (Hg =H-C10 CN = Aaolein | TU = prMP- Q-enal AZ CD Maga, CN. = Methyl n-pwpyl Peton a l oF Tb = pentan- X- — [oped =C= Oly Hg Hs e “— oe . 4. 7 ¢ c c ~¢ —c-Cy-M _s | i 4 b ! Aa, Uy —#F | ¢ =_Stis-prpy| Yotono z I Tus Q4- Pimetylpentun- 3-on_ ~ oO 4 # (C)gC= Heo Ww > Wy- goed =H Bp Len: Mesityl orice mG , | Tues 4-metnyl pent-3-en-Q-on eee y a Se CN Sy ttl qoaverale Tw = 3. ‘afr eyclahansne coral dahyds a CN: = phthalduhyde. cuo TV = BRensone -1/2- dicanbal \dlohy do ; Ho CN. = M- Brimobenzaldshyd— ar IU = 3- BrMobenaaldehy do_ _ & : ae CN: = A>Methyleyclehaxaneno tag matlab ta [intext 12-4] Braco te struduus of ths following Compounds . ca- metro; ayy Preplonelelahyle di) 3- laydrongssranal_ 1 tH cH —d ry : Gant pucget H I ( Gi) a- Hydroxy yclopentane Carb aldshyls (iy) A-oxopentanal C tt a 7 CWy-C= Ma ilac-H_ Hea : sy 438s : (0) ise had ketons _wi4: Fluoyn acetophenone ° ——— if " Z ae - a : “4 : - Formic ad | ee | = Mtho noic acid — ss Cony CN: = Arctic acid __¥¥ xo = Shanice acid _ ee CHCl Coo CN: = Propionic acid “et Iv = prpawic acid _¢ ~ CaO Coy CN = Buturic aciq 4 xy: Butansic -acig Cre cy wey >CHs—OY CDW CN = Seobutyric acid Wy atu-:=Q- nai. Aci WOC- CY _EN-= Oxalic acid Z's _€thanedi ofc acid Yor (2), Coy > Ulutaric acid Ew) - HOOC-CHa Coy CN'= Malonie acid Tv" = erpane dioic add Hoo CMa)e GH > _HOvG - Uy ~O, Cou Ne succinicacid : ers Butane diaic acid Tu. = pentam diotc aacid _— “one Cig)g,o04 > CN: = Adpic acid — | D+ = Hexana dfoic acid H 4 Hove Ca Gown) -Cya wr > HOV=Gh= Gy oy, cau, 3 er (a Te Cu = Phthalic Og aa uo. = ‘Ben aine as icant Ie acid ponean oS Phenyl acebic acid. : Tvs = d-preylethansic acid Tntext 12:6 |. chive the TUPAC names of th Following co pounds 3B 2 y _G) ph Cig Cy GH > Ap 2 Oa ry a soe acid Ty LGaiac soak z f= = OL Coey_ - Us, 3- coal a-enoic acid wh) £ pao 2- mahal wclopertane Ganon Ng =e ot ou 6 Tinitr benseic dif N02 1 -Resenmund Reduction _ * QQ stephn ReacHon So _— * 3 Stand Reactor - _ SE: Caatterman~ Fach vi2acton. : Ss. 2. Pesluchian ey Siani-y (tli -(- ee vara ayy ms -Othts Modo 1 EEE ar =<) : +0 RT Ha Pa, Bsy\ a i ae chloride. ‘ 2 a —— Se 3e oF M3 = 1aalcluhydls Teluie a = _ Benzene COvHe| | LS se oe ooo Ma, 4 eno Se 2. eo Ses Gutahy 2 __ | Ke Hao seaeaeat aie | Repay dl eoride _ we YO ~ Er me CWO Fi (Side chain chloiinats 1 |) Kee hHao8 | croateress 2) (ete = gag —— i x (nob TepRetonas ong) I raed rare Reation | &. From Nitils + RMgX : i Avy) thlonds + Siadey| | nv Cadmium pio tata Se ES TEC Prealation Ronis | Arete or} _ ___ @ aa So BS Pai Qe OWp-CEN + CN3- i aral) —= Cig =e avrg _Strylinitales ——_crignoad Rangent [wt __| Oa | So Wy-c=0 — : — oe Acetone . @ Pe Blaciig-c- cl + Ciy-¢d- CH 2 0H —{ Paglerh oidsa AN biog ca Cadmium heed Cl _ | Be ’ Chogenation 0) Aleshals —__. Oxidahon _o} | Alcohels _ Hydration of _/lteynes 13 Qasholysis of _alKanes _ Aengdroytabtion - > oxtdatiory __ = a ° Mh fa { Asis eet * 7 5 CHa-C=0 FFs - -4 arr. Os =< co o- Te “or fis — 1S pone senna ak | . ene| {ata enol keto i = — he CU = CH atesow toa 5,01 "aotorwion Boe 4 ; Op, — CS Og rl aay ig ny") Sy 2 — 7 oa eh yop op pp POP \) Gaathiy Ojezini & a “ot ft nla “yo - _ Nao _ i a ~~ Corgc0) (Cro) i oe ethana) Petra es 03 2g usp) Tz] cma Ch Mo, "0 CHO = _Bub- one Figo _eMana| _ “2 remain] abe a na oa to bring about ths follow —trancfosm ations” G) Hexan-1-0] © hexanal Cha Oa C2 Wy -CH2 -O ay Cig CHa la Ma CHa (HO *« (h) yshhawata to oydsteranen — oF ox Qi) p- Fhiorotelusna top Fluorbenza|dahyds & two C o's Crbalan2s Za : S) W308 a ; (€tenq) E a (iY) etmanenitik to ethanal ee open SOS cea rage no. [—] |) ate (2. Gaatk ® filly|_Aleahel to _preenal= oo pee | R= a “(Mg rcs > cha= Ol CAO \ Ay TT t _W') Put-a-en to ethanal DD NDUR ERR cd Last: <\ ara =O ) (eons: Cas sta gt ~ to OOF ae) oe fo ee err cue - Cz i "Pi eo — > — qe — I | - | __— _ 6 G wath) ( fom, Cerjgnand Reagent a “= m_A° Alesho| 3. Fam Toluine/ Alia beni - 42 by ty dnlysis of ac duivatives As fom ee (Cox Oat RIYA) og — fee Por a @cSo + Suge Sete Se eee Oh -beo Ethawic acid _ aut acid (2: Fm 1° Alwhal Ci tlohel + Sonus Reagent) OO OW Saat Cis C04 7 \ _ a - Thay Gro sch ° ard | alrasinmn emmy, oy doy a Hao” “Cr03 F HAS°4 f _ Feb ea Tapa Sa TT 7 anborglic 0 acid! 26, fant itor Fp Ces ee —_—— Page No. SP y on 1G Lesa 2 om Fem Toln [aby benzene “a es a : a ee _ tle emo y ih oi a “Gq — in a a — Gensaic_acidi _ *# __}| a =a ~ Lee — fo emg FS ~ i I a oe prpy| benzene —_v : ea Lae Hydrolysis _q} nid _doniveliver Meo rg? Rane — 7 ot P ( eon, C=NMg is | GC reer ie 2A [ito : a, : & (Prmide) = = O-e—o} 1/ G2 NM2 Pais — SW oe ot Nig {| vo 1 C of Cq2-O-e-“ Ms | Gea =c] : Te 2 A —_ ot tig ey frengsg| chit — Ku An gree) a [ ? x0 d | {re O=q 0H y ~ TT 0s OY} - ey _— i ; PR +Hcl eS 1 : ot - : react 1°. I — ligne Ne ~ — [ee Ce =e OM a Ciitatic “acid re ft - CY -C [= hag . | _ = Wav i : i VV ame | compte 2 : : 7 ays Ome OF CaByITE C3. CN ere’) emanic aed arid 4 SN _pantia t 4 ery] Niki. Patel cig -N¥5_ ani ‘ qt ernana mids (A Nee Ce a = CHy-c~ 0} + NH 7 8 ir = A = sai Tape — — acid | y || Date _ 16 Gaat j ; [esate 0) Aotite. chomical_vvactiows to | abgect the fellovsing cnc mua Gutan - \-ol_ to Budanoie. add _ (Mg Ciao tHe anon fa _ Jj -phonyjethavic ag Thi ; -Nitpbemoic ac % a @és . sosito brine i | pene 7 coy 1} | ee ] 3- Nit = acid ngs thi) ; a ( &) Smttylasatopnensna $0 benains=bit-dicatongic _o - _ Ac) Teg i oo eI} Blk erin y AN _ BE ee _ ee sa ___ cb0}y 7 G-Mhatieg| dcato pRonats Benpene-4- co ote aid * WV) Gclohexene to hexane-6—dioic add — erm. y A aon A fa y 00H (i) “Butangy to budamic aad Oo —05-Ca Cig =F a BORO =d oy Tn Ee FFI Thtert 124] Shaw Yow each of Ha faosing compound Can be Converted to benssjc a t q [ETP Che CH fiery are * Bengoic aad Rs ee Rive) Arabophsnens. Ben3eic_acid ee ma mes CR - Benzaic ac} Be leery me 2s Shee ET Beaaaic ac} demmen,, ~ 3. Oxidakon jes{tret ee Wl Fig 4 Halo-foxm est - “5. Alds|_Condonsabion | Coss Alda al condingeien v&- Cannigsqrn Reactor) mia 7 T- EASR oF Benzal _ - R. fridic of Conor yfic acids . WA. Heating effect a Conbsoxi hic acids _ LAO’ SoteiMcation oo} civboxylic aids CAL NPSR Of Corboxyl'e acids. “12 Reaction with NY2 ob Corgopslic acids ig. Reduction of Corbuxylic acids. “414: KEM Se conbomslation ) YANG. WZ : i VAG EASR of ~ Bengui{e Aud. 7 s foaaass ts — he aunie ars OF — gro j | goo} et a a a Hotel Bensoic acid dent undgo © .c. Reaction bees by ab deactivatipg Natura ang Altls(Fect 3 (otal page NOL | favis acid) gets bounded tp carboxy] groeer ; ANP A (Nuckophilic frelition Pagction) <- Reduction _og-_1M\tehela/ wy gpocacls Se Wi 2 —Pcls- — coe a ——— = Owl a - Arcety] chlor do Arai aig FO CC] { Cette chond ) (@theneic acid)|__Socla— CHa Coc] ¥ fy" @teaking. effect of Corberylic fd CHa; f oH Pos /A Ou i = anc | + Ta Ethane } ti -¢ oy __HO/A O,— ¢ anbydnda U : ‘ Viet” ~ T @. conatealien Conboxylic_acid + Aleiele — eaten) ; mM r CH3-C fea) =b_ CH g-0f,=== Cie OCH aC. _erhaywic ethanol acid + Hoo —@: feacion etth Nig (Hrmmanig) CM, Covi it Ont NHo Ethansic acid Ethang mids Tepe acd ei e— 2p G : ath 6 oan Reduetion Of Canboxylic acic by LiAlly, louie # oO Bate BME , CP3cooH 7 = — Chg HOH Leo _ | Ethanic _ athano| = acid + , # GD) Kalbe Electho)ysis turned (KER )| Seconter lai CW Con ———¥ NTO aH > Erna jo = 1 othan @) 2) 7 # (B) Hell-volhand ~Zalinsiey (awa) | Halogenahen 2 CHaWoy —y CH - Conk 2D | { dy | Ethansic acid ete chloe Carboxylic acid s05a—F : “pL Ouscd.o| Anbydids CNSOH [Cry cow Cis] Sate fc a Amid Pcls/Pcl _ | \ “Ciscoe rad ented I \ ET ANY { \ CreecoH : | _ \ Nao, Gao —_ a : : | \ Chet fad eMgeNcey(RVZ) =nng, Hd i - OB. oy = ~S fi F Co KOH OF ethylen ee Ete ee NG! use, ar Cade Cis =o = Oh Cie Ua CHa, ‘2 plabtin Arab | te LF cane: Navy COE] © fing. [ston ro ' on t J Bedok). _ 7 eee : 7 Se] Nao - K _ on® _ qe =4 produc is ee He a i A On AL — A — ree ee || Date_ ae Ga fa - CHO. = _ a - —ESO eofic Nacy Sy Preducr =? @ fy or dil Nao (ox) tT Keone ith — + \eoy y athoast 1x Baby), [oye NaoW - A C¥aChO =i tel Product =?% So* ep a Hor eb} crn eect > Oi oe + heat oH oe —_ cy fen, — p08 = CH OT ade | BR ry =H I Aldo| - men ot b -Muaturet ‘| Beat || —— are Date 93 Gee abe ciycocds + dil Ken —. Product =2 [ _}— : | _ 4 got Sy ¢ : Cla= c= Ole THO =C- Oa, oy tal FT Chace O13 ° Ay cya == s - Wo {| ° ae cao (x74) “CH= EC ata! (BH) x, B- unsadurebed — Condsanry| Campeurs} | | ~ (dj Tot] perrk-B- en“ 2-0 | ao mn ‘i —ter product =2 prpanal_(Prional dabags) Va = = + cy —— | ‘ot 7 | ft {I . ee at 2 I ¢ HET -H “> CH Ch CH= zed | y= Oy = Ho A 1 / 2 . 4 ‘ aor’ poonsokhalt — D ah] Tonmee| | _ Coon] compet : —_—_——_; —__—_— of fay] porta-enel _ Ss hae a + aldadydss + dil HAC) c il Sih alec i re a ; ‘\o" , ‘ [-—— ae ——¥ = Meco r=? G).Cis CHO 4 sole OH ety pred ag os N te a oe $f Ciel td THO Cgc H\t OO CH Mg ao >} on) _& fos + oy 1} y Op a= J [ose cH =< -¥ a oy | [C—O | 4 \ Date = - as Pp i) oe oe — C= Gy ORO pda = % A =o S a * _ = YC __ i aye ar 4 yt Hy a or a a —a ou? md - ~Mo- ay with =] 1°) v e ey, cdtackig Sida Oy —¢ 2) ma \ / { A (ee) ami honor oy _ ¢ aN eh ot B- ovoaturaled comer): compound -{.3-Bieheny| pre-2-en- Lone. 4 2) 1 Ls On - ; —————— 7 —) CHs cuo_ + CHa co Aa a Fe ot ani Ee x %& Cans Date © HA iui Addition RoacHen) SEO Ciiulphiter— S05H "7 1 Addi Hon Camp pig) a Hemi ketal ScHn-z e » Sthalene gtyu) HOH, i CBS, 20 Ete 12 HI, B Oa ena Wo— Oh, WO a aS : ‘ luted tearal Cp O-a ws eS RM. Amine oN —~<5>-Nog Noy —— fe N } OH > NROW HYdixs) amin Nia Neo I Dy-dne 6 Nia > Tiras PRE nad am, tia M9 LODE Way Semin a phen) Mydtegimg 9 /U-GNP = QiU- Sinitwphoy|hdrasing.) ! 27 CG aah) a ies DERN (Emi ts — NR = ce RT as RS a er : a - - a ~ | Ha \OV — Val Tt | r grr anina—“—o i [= Fan Wig 5% 7O= NM, mein gaaiha Hiren 17 filesinyds/ Hetore. — | i gn =W Ey | Fa Pa , mete I} | [ - | 4 H2N =n LO es DE ORS] | img ete Binitn phan) Wi . ° Fe NNN R ea A= rE Semicon’ 4Zora -b_Ha N= emiconasjda Etntect 19-5 | Posdict the products ofthe folloviy actions: =e +HO-NM aie (tae ws I oO HOR ra a . wy CY Ag We LT 7 j i. y® (iy RoCH=SCy= CHO FH —c-N-Bn > = f TT 7 ROHS CHE SN NH SEN 0 } i (© O Sy + We CEN OR OY RT So, cca nit, ease | vt : 7 Page No. [| a |] , ( | [Hees Brendes 19-73] (wre Based) Gd) oh eel thon ths fal fampaunda ——-—} fice din dof thai fa es ra a vines Se --Prepanal propane. Gulatane real ~ Cth Oia) i, ea - C=0 ae HOR as aK 7 Nu © we | PP Ee As Steric effect (Hintrancs) {Meneases bo ny n UL hi | sith difficulty Qulavane *2 Prpare ie < Prepana) Sth ARPS Thenaasing orden vi Fy towards Nuclvopltllic: Aetdi tiav) Reaction ) Bensaldokads p - Talualdehude , p-Nrho bensaldible, . Go : o . ie Os — renin steric _= #¢ bad hindrance. a effect OW) dinwaser "eat eave 7 [ Gwe) Change on _Conbe| Corbsy —] hones aoact poms ik “7 ; sky oF ensolchbyl I Toneasing erd ‘e} waactivitd toons Nuclephitie" ih 2a © saathy) duy/ketonss By FMn04/ KaGra0- ans ¥ Tollens’ Reagent ke Feblngs ane a 3} _ Clg CHO. —————7_ Cig, Cwo}} Fier Feat] 84 ‘lla’: Paager [apnoea Siw Ni tf f @ ~ cus cng CE» + ym + Hoo + Ha gtranal CH, gilven mio. fotug? CH, COMMS ae x Prpan-2or { 4 let | Cay, Cason) + sat) “> fl) Aldoby des ~~ / Sodium potaxium | extept-avemati c __hartareate, If Aldara | ( re Benaalaahyity CLO | Che cno =a Ca,L: Chun? + Yoo ___|| _ Aldatydo © Ped- Brown pet —____— tyO— 7 : COO ————B XX _X_ ie eek on® i yoo Oy XK - } on? Page So 36° | Det a A [Reloform Tei] By Xp 4 Naoy CNgox: - fat Key CKor). —Xa= Za{ fo) ch _ 5 finy cy C=O} =0y ear = o Oh-0-4 = Ca Pe fe _ ioabade chlore Fare ante), eae ji a cust = er CHBra 4+ bs he Ketone EY pmaform (Bmen) Cs, o, — 5 hw Xxx (Y3- Okt Ry OS XX ney eee wih Obaee CHa-OY ~0H peer Fe FRY (ror) l “Yalloo pp - = Text i — —~ en's | _Febling’s Halotorm |_~ | Arete 7 , = |" I | xX x —=— |“ tt Bensaldahyda | x x Oo at Gaathi) hs — > CW, Fea ———— ee _ ee chtowfom ay, Na Example 24. An_oxganic campound (A) ctth_mejeculon ey Chimie acd ) aye (Qc (Beng 100 i we eo Berdse 12-6 Jan | —| HAQVID ely { KAY IST —F Ro Pee wo. [| 32. Ga, | Date __ (© [Ree sea ap Grbac Rall] (fq) Q)_ Reaction with matals/ alkalies - Ny eed Le thet) eT Zee ons fe St tee Nawegs oy Aa? +(@24) Z = age nee Ob ¢— oy =F. Hine 0 v ————S VE mete ee A mee 2 Aro. suid ion Tl J ald : i te 68 [Conberylak | \ lon / Lo: == ! ee eel I 0 oO Ewa co Os ise CN SS Y ° a , ; (Zu) stabilise ERG Sestaby isa I Conor ion Conbiy| ato jon — py withidran| by £ve) I g Eve) Chasse —_ Chany. . ee Te aed sung J acd Tas Tncagayyy docrr sans eas Id Bred CV MF CN NOa Cc | re Cc . — - el —ai aS Cclycpoh S CH cuclacoor)y Noa gence) — NC Og Ge FCA, Coo C] Ul oH coy “HORWY CiCHgdlgawon > CesoH> | 3 Guat _ CMS CHRURYS, CY, OUD Olga or} 4 Encaccsing ord, of acidity : al pe . —b_s Cea C1 apn | aN \RO7 acidic arhueryfy — ohh Cg J o-y — } 1 At . P on gee dewnsasey = : | Trovessing AC) acidic. | | 4 ges Panis an | ) | He —& beni A Nite ~ = ac _ bengeic ac a 7 age ho. _} » 3 Ga __tahich_ acid of each pay Noun hors toad ot s+ te be. “Sige ; = ard Cig | C4 — _ w OE Cay and CligC] CO H _ | ed ree a - GY Cig E Cy Cz COQA and Cgc EC co.n opr we So Ck ts - [Bua Exercise 12.12] and 18-20 aa ke —— (st) Cis CH, CH Comy CL) | a | . 7 or— Cg Cy. CHa Choy Gr) h be E weg fe - (Oe = oj =o) I bits . Sang ath 7 Oh OCW Coop (Y) Oo } ee ee | Page No - a acid ae a) - —. Co _——, J. Nihebengeic_add a ay an _ 3,4 - Aininobensoic acid ea i N °2 Y t 4- Mather bengnic_aad iS | ® OCH . roan . “Sanaaaigh qeidic Shon st . BFR B.) [e eaing Th Goiling Point} Point x dipsle- dipele inteact, { »Tn_Crennal .-for compara al Ma Hytiecanbin_< Et his aw 2. Sobilify X= — ; flop © atoms - 36. ¢ OAA Date __ oo a HM abana tag ete pnp anal iste Pope a oe Absa Cy C0 CaO 0 O1,010C | UscDOH CO any Thay BP [Example 12.2] Aa ing—cempounds lg rs th Measaiiyg thay Oza Ma CHO, CHa. CHa CHa OH CyWs=0-G ic (DH ! Gr) Gr) * etn, Sa cis is i fs in Aldehyde A cahl CHa Oa ta Og | 4 ‘@) Hydyo Corbin) Baa a | Tnvasasi 4 ord gf BP. — intext j.3] trang. ths following compound —— ine y O iy @P- — — Oy. (Ho SM Oaad Ohs0 Oke C3 We CH r @) __ &> @&) fiidohyds Alelul et Hy drocaby) | wire? ar : ee se ee eee < Cire -Y Bensaldakyd- prpavia! Ze ies oachwe- “* More veactive. towards ruicophilic tooad Nucleophilic addy Hon veactor addition vaactive_ Dus fo clecraastor) in polarity by vaonnance—_{n” bergaldahyda_ Yoto Emenciss JQ19 12:13 Tae ——

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