BAI TAP OA HOC UU CO Tai ligu danh cho: * Hoc sinh chuyén Hoa. * Sinh vién cac truong Dai hoc. # Gido vién Hoa hoc. 08 © 2009Li 966.60 $ a Héa hoc hitu co la mét trong nhitng b6 mén rat quan trong trong linh vue Héa hoc néi riéng va pham tri Khoa hoc ty nhién néi chung. Tuy nhién hign nay, cdc tai ligu tham khdo vé bai tap héa hoc hitu co la khong nhiéu. Vi vay viée tang hop céc tw ligu dé cd mét tai liéu tham khéo bé ich va dé tiép thu hon la vige rét can thiét Bai tap Héa hoc hitu co la mt tai ligu duge bién soan dya trén vige tong hop lai tit nhiéu ngudn tw ligu khdc nhau theo tig chuyén dé dé hoc sinh, sinh vién dé ndm bdt, Tai ligu gém hai phan: Phan bai tap theo ting chuyén dé va phan hwéng dan gidi. Cac bai tp trong tig chuyén dé dugce tuyén chon ki luéng nhim muc dich dim bdo cho cdc dang bai tap khong tring lap va hoc sinh, sinh vién cé thé tiép can nhiéu huéng ra dé khdc nhau tie cling m6t dit ligu kién tite. Bai tap Héa hoc hitu co’ bao gém hai tap: - Tap 1: Gém bay chuyén dé twong ting voi n6i dung thudc phan dai cuong héa hoc hitu co va phan kién thie hoa hitu co tie bai alkane dén cetone (theo chucong trinh héa hoc phé théng). - Tap 2: Gém cdc phan tir acid carboxylic dén cdc hop chat di ving. Ngodi ra con minh hoa thém m6t sé bai tap nang cao tang hop cdc chuyén dé. Vi la tdi ligu tong hop lai cdc bai tap nam trong cdc gido trinh, sach tham khdo bai tap hitu co, cdc dé thi hoc sinh gidi nén dap an cho tieng bai khong thay doi theo dap an cita ting tai ligu tham khao. Vi vay Bai tap Héa hgc hitu co khéng phai la m6t tai ligu do mét nhém tac gid bién soan ma chi la tai liéu tong hop cé chon lea tie cde nguén te liéu 6. (Téng hop tir nguén Internet — copyright © volcmttl@yahoo.com.vn).Bai tp Héa Hitu Co — Tai ligu danh cho sinh vign cdc trudng Bai hoc a a ee Part: 1 HIEU UNG HOA HOC On Om Sip xép cée nhém nguyén tir sau theo chigu ting din higu img twong img, biét trong cau a thi R ndi trac tiép véi S. a, Higuimg—eia: (1) -SR (2)-SOR (3)-SOR b. Higuimg—C cia: (1) RNCO- (2) RNCGNR) - (3) (RNCE'NR2) — ©. Higuimg +C cia: (1)RCO-N(R- 2) RCENR)-NR- (3) RCH-NiR)- Bai 2: Dya vao hign tugng cOng huéng, viét cong thite gidi han (néu c6) cita cde chat sau day: a. CH-CH-CH,-Cl, &. CoHS-CN. b. p-NOs-CoH:-NEb. 4d. Colls-CHs. Giai thich tai sao nhiing vi tri o- hay p- cla hgp chdt CsHsCH)C!l tuong d4i gidu dign tir trong khi 6 tai cée vj trio- hay p- etia CoHsCChs thi thigw dign ti Bai 4: Dya vao higu tmg dign tit, hay so sénh tinh acid cita cée chat sau day: a. CsHsOH (1), pCHs0C¢H,OH (2), p-NO;CsH,OH (3), p-CHsCOC¢H,OH (4), p-CHsCsH1,OH (5). b. CHsCH:COOH (1), CICH:COOH (2), CICsH4COOH (3), IGH«COOH (4), ICH:COOH (S) ic chit sau theo thir tye gidm dn tinh base: < ™ < NED NER Bai Oo 2 6) a Bai 6: So sinh tinh acid cha cée hop chat sau: (1) (CHs)sC-COOH ; (2) CHSC! (3) CH,CH,CH=CHCOOH ; (4) (CHs);CH-COOH ; (5) CH)~CHCH;CHsCOOH. Bai 7: So sinh tinh base cita cée hop chit sau: Yr Se NH: NH? sh @) 4) (3) ee — Copyign 6 200 toismllasaboe con a “aBai t8p Héa Hifu Co — Tai liéu danh cho sinh vién cdc trudng Dai hoc ete te ie en ee a a ae ae See Bi jguvi ta nhin théy ring alcohol tert-butylic tc dung ngay lap tite véi acid HCI dém dic dé tao) thanh tert-butylchloride bén ving trong khi alcohol n-butylic trong ciing diéu kign phan img rit chm, Bai 9: Xéc dinh higu tmg cita cc nhém thé sau khi lién két véi gée phenyl: Cl, -C(CHs)s, -CHO, -NO2, CEN, ~CH,CHs, =N(CH)s Bai 10: Dya vio hign tong cng hudng, viét cong thie giéi han (néu e6) cua ede chit sau day: a. Aniline, €. Vinyl Bromide. b. Buta-13-diene, a. Acrolein. Bai 11: So sinh d6 bén cla cdc ion sau: a. (1) @CH.CHs, (2) ®CH(CHs)2, (3) @C(CHs)s b. (1) @CH.CHG, (2) @CH.-0-CI & (1) C{CH)s, (2) @CHsCaH, (3) @CH(Cots o Bai 12: Xée dinh base lién hgp cia cdc acid sau theo quan diém cia Bronsted: HO, CoHsNHs0, (3) ®CH:-NH-CH, CHOH, 130". Bai 13: So sinh d6 dai lién két C-Cl trong CHyCH,Cl va CH)=CH-Cl. Gidi thieh. BAi 14: Giai thich sy ting dan nhiét 49 s6i ciia cdc alcohol sau: Alcohol CHSOH CHs0H CHO Nhigt 49 801 CC) 6 BS O72 138 HOH BAi 15: Cho ba gid tr nhigt d6 sOi: 240°C, 273°C, 285°C. Gan ba gid tri trén vio ba dong phan o-, m-, p- cua benzenediol cho phii hop. Gidi thich ngin gon. Bai 16: Giai thich sy khae nhau vé nhiét d6 sdi trong day céc chat sau: Q) @) 118°C 11PC 256°C 187°C ‘Bai 17: So sinh kha nang tan trong nude cia cde chit sau a, (1) HO(CH;),OH, (2) HO(CH;)sCHO, (3) CsH:CHO, b. (1) CelisNHsCl, (2) CelisNHs, (3) CoHsNEb. Bai 18: Acid fumaric va acid maleic ¢6 cac hing sé phan li nde 1 (ki), nde 2 (k). Hay so sinh cde cp hang sé phan li twong tmg cia hai acid nay va giai thich. Bai 19: So sinh nhiét d6 néng chay va tri sé pK, cita 2 acid sau: He, cooH os, “ H aM; H \ OCH (1) acid iso-Crotonie (2) acid Crotonic — — Z Gonvish © 309 Timmins w we ee eeBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc tru‘dng Dai hoc mare te ae — oe ee ee ok BAi 20: Xéc dinh tim base manh nhat trong céc alkaloid sau: aaa ee sy wl Ow? eo CHO Xo -OCOCH, HH cy CoocH, Vindoline Nicotine otthotthott hott tte tttottottoost**ost#tost#tost*tontthogtttostt cs tog Part: 1 HUONG DAN GIAI Bai 1: Sap xép theo chiéu ting dan higu img dign tir: a. (1)@)>()>6)>@) b. 2)>()>G)> > (0. Bai S: Chiéu gidm dan tinh base: (3) > (1) > (4) > (5) > (2). Bai 6: Chi tinh acid: (1) <4) <8) < (5) <2). Bi base: (3) > (4) > (5) > (1) > Q). Bai 8: Xét 2 phan ting sau: ting da Chigu gidm din tr (1) (CHs)sC-OH + HCL 5. (CHs)s 11+ H20 06 vain tc phan ting lav (2) CH;CH,CH:CH>-OH + HCL —! 5 CHsCH2CH,CH)-Cl + H,0 c6 vi 'e phan img la va Co ché phan img di 1a Sy' hay Sy? déu trai qua giai doan tao carbocation. Carbocation cing bén thi phan ‘img xay ra cng wu tién, Se div; >> v2 la do carbocation (CH3}sC® bén hon CH;CH2CH2CH) nhiéu, igu nay gidi thich da vio +1 cia (CHs)sC® én hon nhigu so véi +1 ela CHsCH2CH2CH2®. Bai hi lién két v6i géc phenyl thi NO2, -C=N gay higu tg -1, -C - Clay higu img -1, +C - -N'(CHs)s gay higu img —1 - -CHO, = -C(CHs)s gay higu tmg +1 - ~CHCHs gay higu ting +1, +11 BAi 10: Cong thite gidi han: a. Aniline wh A b. Buta-1,3-diene: — “CH;-CH=CH-CH>- ‘CH,-CH-=Br ©. Vinyl Bromide: 4. Acrolein *CH_CH-CH-O- Bai 11: So sinh d6 bén: a. B)>@>(). b. 3)>Q)>() © 3)>Q)>(). Bai 12: Xét bing — — Z Gonvish © 309 Timmins «aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc tru‘dng Dai hoc ete te ae ee ee ee oe es oe acid HO ‘CoHsNHS CoHsOH HO base lign hep On CeHsNF CHO" HO Bai 13: BO dai lign ket C-Cl trong CH>-CH-Cl ngin hon trong CHy-CHa-Cl vi: + CHs-CH)Cl 6 higu mg -L AN 8 A = CH= CHCl Ngoai higu tmg I cén c6 thém higu img +C lam giam dé dai lign két C-C1 (lam d6 dai lién két CCl ngdn hon lién két C-C] binh thuéng ding théi lam lién két C=C dai hom 46 dai ign két C-C binh thuémg) Bai 14: Do ca 4 alcohol déu tao cé thé tgo duge lign két hydro lién phan tr nhung do khéi lrgng phan tir cohol ting din nén nbigt 49 sdi ciing ting din. Bai 15: Ta cé ba déng phan o-, m-, p- clia benzenediol OH Za CI Yo oH (1) 240°C (2)273°C (3) 285°C on on (0) c6 lign két hydro ndi phan ti nén nit d6 s6i 1a bE mht. (2), (3) déu cé lién két hydro lién phan tir nhung lién két hydro cia (3) bén hon ca (2) do it bj cén tré ve mit khéng gian. Bai 16: = Taccé nhigt d6 s6i cia (1) < (2) la do hai chit nay khéng tg0 duege lign két hydro nén nhigt d6 s6i phu thude vao khdi Iugng phan te - Lai c6, nhiét d6 sdi ca (4) < (3) la do mae dit ca hai chat déu cé lién két hydro lién phan tir rnhung lign két hydro cia (3) dang polymer cén cia (4) dang dimer. Bai 17: Kha ning tan trong muée cia a. ()>Q)>@). b. (1)>G)>Q). Bai 18: Xét cdc chuyén héa: woo woo a -ooc H ‘COOH =H" H ‘coo -W H coo" F Axit fumaric Fr EY ‘coc. coo on =e = “S = ar oo Sa wn ait mali Copyign 6 200 oismllasabes con a aBai t8p Héa Hifu Co — Tai liéu danh cho sinh vién cdc trudng Dai hoc a ee em ann ee So me oe ee ee = ky(M) > ki(F) ld do M cd kha nang tao lién kér hydro ni phan tt, lign két O-H eiia M trong qué trinh phan li thir nhét phan cyc hon so véi F va base lién hop M’ eting bén hon F- = ka(M) < ke(F) la do lign két hydro ni phan tir lam cho M' bén, kh nhuéng protone hon so véi F*_ Ngoai ra, base lién hp M" lai kém bén hon (do nang rong tong téc gitta cde nhém ~COO™ lim hom) base lién hgp F*. Bai 19: So sinh - _ Nhigt d6 néng chay eta (2) > (1). + Tinh acid cia (1) > 2). Bai 20: Xe dinh tm base manh nhdt | £ NOH CH; COOCH, Nicotine Vindoline = Alkaloid 14 cfc base tir nhign, tinh base t§p trung tai di t6 N cho nén nguyén tit N cng gidu electron thi tinh base cing manh. - Véi Vindoline thi N(b) trong nhan indole cé tham gia qua trinh cng huéng nén nghéo electron hon N(a) nén tm base manh nhat cia vindoline 18 Na), - V6i Nicotine thi tinh base cia N(a) va N(b) gan bang nhau tuy nhién N(a) tham gia vao qué trinh céng hung cho nén tam base manh nhat eta Nicotine I N(b). lotthotttrottHotthotthot hot hott toot ttostttostttostttostttostttost*tostttos Part 2 DONG PHAN 1 wc ‘Béng phan cle ‘Béng phan trans iu tao cia cae chat sau: 1g phan a. CsHio (chtta mét vong). CoH b. CsHuOH, a. CHCl — — Zz Gonvish © 309 Timmins aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc meee Se we ee ee ee es es ee At nao sau day 6 dng phan hinh hoe, goi tén cdc déng phan d6 theo danh phdp Z, E. a, (CH):CH-CH=CH f. Cao su thién nhién b. CHs-CH-CH-CH; g Nhya Gutta-percha © CH-CH @.— C3Hs-C(CHs)=CH-CHs i, 1,2-dimethyleyclopropane € CHs-CH+C=CH-CHs h CHSCH: I-CHs ya theo gia tri momen luting ee eta fe dng phan hinh hoc, hay cho bit trong cde chit A, B Bai sau day déng phan nao la cis, dong phan nao la trans a. FHC=CHF ha=0D hs = 2,42 D b. CH-CH-CH-Br a= 1,57D. bis = 1,69 D & ppNOMCeH-CH=CH-Colly ha =3,11D is = 4,52 D Bai 4: Nhitng chat sau day cé thé tn tai bao nhiéu déng phan lap thé. a, I-phenylethanol b. 2-chlorobut-2-ene © 1,2-ibromopentane. Alanine, Trinh bay cdng thite chiéu Fischer va xéc dinh céu hinh tuyét déi cia cdc déng phan c6 céu tao sau cH, oH cooH b rE ‘Na BO 4“ 4 @ O) © : Vist cng thite chiéu Newman dang bén cia: a. (CHs),CHCHCHs, b. CH)CH+CHs, — CH;CHO. Bai 7: Chat A 1a mét acid hitu co cé néi déi C=C va khong quang hoat. Tuy nhién A cé déng phan hinh hoc va co céng thite phan tir la CsHsO2. Khi hydro héa A thu duge sin phim B cé tinh quang hoat, Xac inh hai chét A, B va viét phuong trinh phan tmg xay ra. a, CH;COCH,CHs, b. CHsCOCH,COCH:. &. CoHsNHCONHC&Hs. Copyign 6 200 oismllasabes con a “aBai t8p Héa Hifu Co — Tai liéu danh cho sinh vién cdc truding Dai hoc ete te em ee ee a a a ee ee ae ee BAi 9: Hay ghi déu * vao bén canh nguyén tir carbon bat déi va xéc dinh cdu hinh tuyét d6i ctia Serine, H _ Pe IL KO Adrenaline, Menthone, HON A ? os NY <0 Ty l ‘CHNHCH, wen cH, cHOH HO SN én, Serine Adrenaline (Corticoid) Menthone Bai 10: Viét céng thite dang hé bién va cho biét loai hd bién trong hai tredng hgp sau: a, Cyclohexanone. b. (CHs):CH-N=O. Bai 11: Xéc dinh céu hinh cia A, B (dang cis, trans) va viét cau dang ghé twong img H H Gp oS A B Bai 12: Cho cdc phan tmg sau: (1). CsHsCH,CH(CH3)OH + CISO,CsHsCHs-p "> (E) + [a }p= 133° H (2) (E)+CH\COOK — TsOK +(F) (Ts laki (3) (F)+ KOH — CH;COOK + C6HsCH,CH(CH;)OH. [aJo =-32,2° a, Xéc dinh cdu tric cita (E) va (F) va cho biét phan img (2) thudc logi phan img gi. u viet tit ela -SOsCsHyCHs-p) b. Cho biét phan img thay phan céc ester logi nhu (F) trong méi truéng kiém véi sy hign dign cua 1,0" nhu sau: RCOOR’ + H,0" <2 RCOO"H + R'OH Dya vio cdc két qua trén, hay gidi thich sy thay déi déu nang suat quay cye [ a Jp clia alcohol ban dau vva sin phim. Bai 13: Viét tit ca cdc déng phan ca phire chat [Co(bipy)sCl:]" véi bipy la: O<2 Bai 14: Quang phé hap thy dign tir cua formaldehyde c6 ba cyte dai & 295 nm, 185 nm va 155 nm. Néu cho formaldehyde te dung véi Hy e6 xtic téc Pt thi ba eye dai ndy cén khéng. Gidi thich. Bai 15: Viét cong thite cau tao cac dong phan mach hé co céng thie phan tir CsH4BrCl, c6 dong phan quang hoe va chi c6 mot carbon phi di ximg trong phan ti —— - Copyright © is waismaavahoa sa «aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién cdc trudng Dai hoc etre te ae ee a os aa ae Bai 16: Styryllactone duge phan lap tir thye vat. Viét céng thite cdu dang cdc cp déng phan déi quang va goi tén styryllactone theo danh php IUPAC, HO Bai 17: Khung carbon cia cdc hop chat terpene duge tao thanh tir cdc phan tir isoprene két ndi véi nhau theo quy tic “dau — dudi”. Vi dy, néu tam quy ——F ude: (dtu) CH:-C(CHs)}-CH-CH, (dudi) thi phan tir o--mycrene duge két hop tir 2 don vj isoprene. Dya vao quy tic trén hay cho biét trong céc chit sau a—myerene diy, chdt ndo ta terpene va chi ra don vj isoprene trong khung terpene &6 on po Acoron HO Axitabietic Podophyllotoxin Bai 18: Viét cong thie Fischer cita céc eb Bai 19: Viét céng thite chiéu Fischer cdc déng phan lap thé ca acid 2-bromo—3—methylsuccinic va chi ra cdc c§p déng phan ddi quang va céc c&p dng phan khéng ddi quang trong cdc dong phan lgp thi Bai 20: C6 ba hop chat: A, B va C no-¢_)-¢ ~Y HO ° CH A B c a. Hay so sinh tinh acid cia A va B b. Hay so sénh nhiét 46 s6i va dé tan trong dung mdi khOng phan cue cita B va C. ©. Cho biét s6 ding phan lip thé c6 thé e6 cia A,B va C. 1 — ee Copyright © 2009 volemttl@yahoo.com.vn pie ie OER 9Bai tp Héa Hifu Co — Tai ligu danh cho sinh vién cac trudng Dai hoc an ae oe ke ee es - - Part 2: HUONG DAN GIAI Bail: +t edie déng phan cdu tao: Sx242~ a. BG At bao hoa A= Sz2* 7-10 =1, theo dé CsHio 06 chira mét vong (A =1) nén la cycloalkane. CsHjo (¢6 1 vng) 6 5 déng phan cau tao phi hgp: CH, /\F® LJ Ch Hs 5 da bit ba 5x2+2-12_) 4 se. C6 8 dng pha , Cott) OH 6645 bit bao hia = 2-2-1249 nen 18 alcohol no dom che. C6 8 dng phn ©. CeHyc6A 4d. CyHyCl c6.4=0, c6 4 ding phan. Bai 2: Cac chdt c6 déng phin hinh hgc la b, ¢, d, fg, hy i ~ Véib, c,d chi e6 2 ding phan hinh hoc. - £(cis-polyisoprene) c6 déng phin la g (trans—polyisoprene) va nguge lai. én nhau nhu mot hé cé din, 06 5 déng phan, - heé déng phan hinh hoc vi cé sé lé lién két C=C H, zl =C He cus - ie6 hai déng phan hinh hoc do vong cyclopropane phing (mat c6 dink). HAH HOA CH Vz EN. CH; CHs CHs a b © B B x Bai 4: a. (A) co LC" nén c6 2 ~ 2 déng phan quang hoc, (A) khéng c6 déng phan hinh hoc. Vay (A) 66 2 déng phan lap thé. b. (B) c6 2 ddng phan lap dng phan hinh hoe. ¢. (C) c6 2 ding phan lap thé la 2 déng phan quang hoc. d. (D) cd 2 ddng phan lap thé 1a 2 ddng phan quang hoe. meen ie we = Copyright 2000 talonlasaimsoonta toBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc aaa ee (a) (28)(38)-dichlorobutane. (b) Acid 2R)(R)-2,3-ihydroxy-2,3-dimethylbutane4-al-I-oic. (©) 2R)3S}-2-bromo-3-chlorobutane. CH CHO CHy H cl HO CH, Br H cl H HO Hy cl H CH; COOH CH3 @ (b) © BAi 6: Viét cng thie chiéu Newman a. (A) 06 2 dang bén: b. (B) c6 1 dang bén: e, (C)c6 1 dang bén: Bai 7: Al CHsCH=C(CHs)}-COOH B la CH\CH,CH(CH:)-COOH. Bai 8: ‘Sng thite hé bién a, Hé bién ceto-enol cita dang ceto CH\COCHsCHs la cée dang enol CHsC(OH)-CH-CHs ; CH;-C(OH)-CoHs b. Hé bign ceto-enol cla dang ceto CHsCOCH;COCH; 1a ede dang enol $(OH)-CH2-C(-O}-CHs ¢. H6 bién ceto-enol cia dang ceto CsHsNHCONHC,Hs CHsC(OH)=CH-C(=0)-CH ; CH» la dang enol CoHs-N=C(OH)-NH-CoHs + Copyright © 2009 Taizmavahoe com ReBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc -—— = a xxdc dinh edu inh tuyé ~ HO Ne R oO H re ~CH, CH; R Bail ng thire dang hé bién a, Cyclohexanone, Hé bién ceto-enol OH aN — So NS b. (CH3),CH-N=0. Hé bién nitro-axi H,C-CH-N=O0 <= H,C- ¢-N-On | CH, CH, Bai 11: Xac dinh cdu hinh cia A, B (dang cis, trans) va viét cdu dang ghé tuong (mg = Bla trans-decalin = Céu dang ghé ota (A), (B) aes ad (a) @) —— eh Copyright © 2009 volemttl@yahoo.com.vn roBai tp Héa Hifu Co — Tai ligu danh cho sinh vién cdc trudng Dai hoc meee Se ae ee i ee es - e- Bai 12: a, Gia sit alcohol ban dau cé [op = +33° 6 cdu hinh R => (E) cing cé cau hinh R vi phan img khong xay ra tai C’ ma tai O, trong khi 46 (F) e6 edu hinh $ tai phan tng xay ra tai C’ + Gia sir edu tric ban dau ciia alcohol 1a: CH; ol H’{ >on ALC) = Cu trite cia (E) li: Cu trie cia (F) la ii CH; al - HH] ots {> CHCHs CgHCH Ag -O0 - Phan img (2) 1a phan img Sy* => san phim alcohol cia phan tmg (3) 06 céu hinh nghich véi cu hinh alcohol ban dau. b. Phan tmg (1) va (3) khong lam nghich edu hinh, nguge lai phan img (2) c6 su nghich déo cdu hinh do phan img xy ra theo ca ché Sy* Bai 13: Quy usc biéu dién bipy bing mét cung Idi, CY i a oF cis Cl Trans a. Bong phan cis, trans: b. Déng phan quang hoe: Bai 14: Ba cye dgi hip thy 295 nm, 185 nm va 155 nm twong img véi sy chuyén dai dign tir mite ning lugng: nn’, > 0°,x—> n. Khi téc dung véi Hy/Pt tgo ra nhém OH nén lién két x khOng e6n, do vay ba eye dai khéng cn, —— ee a Copyaiht © 2009 Taizmavahoe com aBai t§p Héa Hifu Co — Tai ligu danh cho sinh vién cdc trudng Dai hoc Seem te ae = ee i ee Bai 15: Déng phan quang hoc: H : H I 1 I CH= cual | are CH=CH \ Br 1 Br Bai 16: = Tén: $-hydroxy-7-phenyl-2,6dioxabicyclo[3.3.1]nonane—3-one fu dang: = Céng thet done von aco0 oH ra e on By HO HO LOH Ba(OH) cs # Bai 19: Ta c6 4 déng phan lap thé COOH COOH COOH CooH H—\}—cH, CHG H CH H iH CH; H Br Br H H Br Br. H COOH COOH COOH COOH o ay am av) nee w Corigh © 000 talantiasalmsoonn iaBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc eae a ee Oe @ nan) (i) dia dia dia dia amy *enan—”~«V) Bai 20: So sinh, ii thich a, Tinh acid duge dinh gid bai sy dé ding phan li protone cila nhom OH. Kha ning niy thug lgi hi c6 cdc higu tg kéo electron (-I hoc ~C) nim ké nhém -OH. 6 A vita e6 higu img lign hgp (C) ‘va higu ting cm ting (“I ; 6 B chi c6 higu ting (-1). Tinh acid eta (A) > (B). b. Lin két hydro lam ting diém si. Chit C c6 lién két hydro ni phan tt, B c6 ign két hydro lién phan tir nén nhigt d6 s6i ctia (C) bé hon nhiét dé s6i cia (B). (C) 06 49 tan trong dung mdi khéng phan exe Ién hon (B). c. (A), @) abu c6 2 tim bit déi, hai nhém thé c6 thd nim @ 2 phia khéc nhau cia vong cyclohexene va ching c6 thé t6n tai 4 déng phan lap thé. (C) c6 4 tam bat déi c6 16 déng phan. ae OL ky chs l oS Ho ROMERO HERE RO HERO HERO HERS HRS HE Sgt EF ag EE SION SEER SHEE SHE SEER CSttFCS eh _— Copsrighe 8 2000 talomlasabmsoonta éBai tap Héa Hifu Co — Tai ligu danh cho sinh vién céc tru‘dng Dai hoc ee ae ee ee es — e- OR 0 on oy? a. CHs-MgCl + CHsCOCH - & 2C:HsOH > b. CHSCIACI+ KCN > h, Pyridine + C2HsI > ©. CHsCl+ HyN-CHs—> i. CalsOH + HCHO CellsCHO + CH;CHO > fe. CallsONa + CHsl > f. CoHsOH + CH30H > k. CH,CH,CHEOSO,H)CH, + H0 > La sCOOCHs + OH > Bai 2: Xac dinh cac chat con Iai trong cdc so dé sau va néu co ché tao ra ching a, Hoan thinh so dd sau: CH3CH2CH: (A) ——> B ——> ON > A b, Hoan thanh so 46 sau: cH, CH,CH=CH,(4) 8) —>(C—@) ap u-don, @ OH ¢. Hoan thinh so dé sau: HC=CH—s(®)—> CH, GH -CH, -CH, CECH, OH OH ho biét sin phdm tao thanh trong cde phan img sau, néu co ché phan img a. CH-CHeCH: + Ch E> b. CH=CH + Bry +> ¢. H,C=CH-CH=CH, “Bee d. CcHsCHs + Clr > Bai 4: So sinh kha ning phan tmg cia ede ep chit sau: a, Theo Sx': CHyCH,CH,Cl (1) ; CH=CH,CH,Cl (2). —e + 2 —— Copyright © 2009 volemitI@yahoo.com.vn poe eee OR “&Bai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc eee te we ee ee ee b. Theo Sx: CH,-CHCI (1) ; CHsCHRCI(2). Theo Sy': p-NOCsHiCH2Cl (1) ; p-CHyOCsHiCH2CI (2) ; C CH:CH,Cl (3). Bai 5: Ding mii tén cong chi ré co ché chuyén 7-dehydrocholesterole (1) thanh vitamine D; (II) va cho bit cdu dang bén cia nd. Biét trong céng thite duéi day: R la: -CH(CHs)-(CH2);-CH(CHs)2 wel ke A Bai 6: Cho so dé phan ttng: chs am CHy a. Vit co ché phan img va eéng thite edu tao ede sin phim. b. Goi tén edu hinh cita B, C theo danh phap R, S. Bai 7: Hay gidi thich sy tao thanh nhanh chéng 2,4,6-BrsCsH:NH2 (D) khi cho p-HsN-CsH.-SOsH (A) hoje p-H:N-CsH-COOH (B) tuong tae véi dung dich nude Br. Bai 8: Hay chi ra co ché phan tg va sin pham cudi cita phan img c6ng Br, (1:1) véi nhiing chat sau: a. Acid maleie (1). . Acid famarie (2). ©. But-2-ine (3). “™ “™ H,C-C oO 2 8) Bai 9: Xét phan img thé: RC]+OH™ > ROH + CI cé biéu thite tée d6 phan ing 1a: v = k[RCI] hoje K{RCI[OH"] Hy a. Cho mét vi dy cu thé vé RCI trong mdi truéng hop, gidi thich. b. Sy dung méi gidi cia tert-Butyl bromide trong acid acetic xay ra theo co ché nhu sau: (CH,),CBr — (CH,),C* + Br @ (CH,),C” + CH,COO™ + (CH,),COCOCH, (2) Hay gidi thich tai sao, khi ting ham Iugng Sodiumacetate (CHyCOONa) thi khéng lam ting toc 46 phan img, — — Copyright © 2009 woman com aBai tap Héa Hifu Co— Tai ligu danh cho \h vién cdc trudng Bai hoc te em an ee Bai 10: Hop chit 2.2,4-irimethylpentane (A) duge sin xudt So ae a ee i quy m6 Ién bing phuong phap ting hop xiic tde tir CyHy (X) v6i CaHio (Y). A cling e6 thé durge diéu ché tir X theo hai bude: thir nhit, khi 6 xiie tic acid vé co, X tao thin Z va Q ; thit hai, hydro hoa Q va Z. Vid cde phuong trinh phan tng dé minh hoa va tén ede hop chit X, ¥, Z, Q theo danh php IUPAC. b. Ozone pha Bai 11: Giai thick: a. Tai sao phan tmg sau khong ding dé CHSCH;CH;ONa + (CH;)sC-Br <> (CHs)sC-OCH;CH,CH, b. Sin phim chinh cia phan tmg nay 1a gi va Q sé tgo than 4 hop chit, trong d6 c6 acetone va formaldehyde, trinh bay co ehé, éng hgp tert-butyl propyl ether. ¢, Hay dé nghj phuong phap téng hgp tert-butyl propyl ether t6t hon, Bai 12: Xir li a. halogen cetone véi base man tgo thanh cée sin phim chuyén vi. Sr chuyén vi nay goi 1a phan tmg Favorski: «- chlorocyclohexanone sé chuyén vi thanh methyleyclopentanecacbocylate khi co ‘mit CHsONa trong ether. Hay xée dinh co ché cla phan ting nay. ° OCH, + CHjONa 4 NaCl Bai 13: Cho cdc phan img sau: But~2-ine—“*»A (1) ; But-2-ine >A (2). Trong 46 A,B 1a 2 déng phan lap thé. Khi ché héa riéng biét A va B bing acid manh thi chang déu chju sy chuyén hhéa sau: Dong phan héa vj tri, déng phan hoa khong gian. a, Xéc dinh A, B va cdc san phim chuyén héa néu trén. b. Viét eo chi cho qua trinh chuyén héa trén, Bai 14: Khi dun néng 2-methyleyclohexane—1,3-dione véi but-3—ene-2-one trong dung dich kiém ngudi ta thu duge mét hgp chit hiu co (san phim chinh) c6 eéng thre Cj)Hy4Op. Hay viét cong thite cd to ci sin phim nay va gidi thich qua trinh tao ra né. Bai 18: Cé mot phin tng chuyén héa theo phurongtrnh sau: cH I + CH-C—H + a, Giai thich co ché, b. Néu thay cht ban dau 1a p-xylene thi sin phim nao tao thanh, Copyright © 2009 wosmievahoa com @Bai tp Héa Hifu Co — Tai ligu danh cho sinh vién cdc trudng Dai hoc ae Se ae ee ee - e- Part. 3 HUONG DAN GIAI | a, CHs-MgCl + CsHgCOCHs > (CHs)2C(-CsH3)OMgCl b. CHsCH:Cl+ KCN —.5 CH;CH:CN + Cr fe. CHCl + HjN-CHs > CH3HNCHs + HCL . CH3CH3CI + H,0 —-» CH,CHOH + HCL fe. CeHsONa + CHst > + Nad f. CoHsOH + CH}OH > CHsCoHiOH (0-, p-) + g. 2C:H;OH —>C;H;0C)Hs + HO h. Pyridine + CHel —%> [pyridine(N=}- CHT iL CaHsOH + HCHO —© 5 (o-, p-) CHjOHC CiHsCH=CHCHO + 1,0 k, CHsCHsCH(OSO3H)CHs + 1 CH;COOG:H; + OHT + HOH Bai 2: +Br, CH:CH2CH; (A) > CHy CHCHs Kobi, CH 3CH=CH) Sp ip Ey NHN a9 e [s HsCH2CH3 ate ok the CH CHCH; ee CH;CH=CHy 1 OH { Ax Sx Ei (CH,CH=CH,(A)—> CH3CHCH; (B) > CH;CHCH; (C) > 1 I Br OH CHMgcl CH, aot, S CHIC CH: D)E> CH C-GHD CH O-CH, @) 4 a évect 88 bn i HYNi HC=CH CESCHO, ) _, cH,-cH-C=C-cH -CH, = CH, - CH -CH, —-CH, -CH-CH, os iH tb 3 —_ a Ze Copyright © 2009 wosmivahve com aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc meee Se ae oe ee - e- 3: a. CHs-CH=CH) + Cl —“@° >C1-CH, ~CH = CH, +HCI b. CH=CH) + Bry +> Br-CH)-CH;-Br €, HC=CH-CH=CH) + Bry —+-9(1) + (2); (1) CICH,CH(CCH=CHL ; 2) CICHZCH=CHCHCI dd. CHsCHs + Ch S88" 5 p—CH,C,H,C1+HCL Bai 4: a. >) b. @>W) « @>@>a Bai 10" F? Céu dang bin Strans | Bi 6: a. Ca ché Ay, Céng thite cla B va C CH3C=O CH; 1. CgHsMgBr HO—|— CH ome i aio - Ts 2. Ha (A) CyHz;—| — C3H7 CaHz CH3 HBr dac Br—t—CyHs —— C2Hs——H CaH7 b. B: (2R\(3S}-2-phenyl-3-ethylhexane-2-ol, C: (2R)(3S)-2-phenyl-2-bromo-3-ethylhexane Trong nude (A), (B) tin tai dang ion lung eve: + p-HiN-CoHy-SOsH (A) p-“HyN-CoHy-SOs (A’) — Copyright © 2009 wosmilevahoa com om ee a et ne ee ee =mBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc re Se ae So en ee ee + psHaN-CeHly-COOH (B)—p"HsN-CsHe-COO™(B") Mat nhém SOs" trong A’ hoe COO™ trong Bla do: Bry > Br! + BF Enhom SO5- tit carbon ciia nhan thom dé Sau dé téc nhan clectronphile (Br°) cong vao nguyé trong A’ hoc COO trong B’, Sau dé xay ra qué trinh téch H’ dé tao thinh nhém —NHz, Nhém NH véi higu tg —C sé dinh huéng nhém thé tiép theo vao vi tri ortho- theo so dé sau: = $05 SS \ Br Br Br MH rm ] az + 2Br, a SS 4 ‘Truong hop a, b xdy ra theo co ché Ap néu tren. a. Phan img tgo thinh hin hgp raxemic gm 2 acid: acid (2R)(3R)-2,3-dibromobutanedioie va acid (28)(38)-2,3-ibromobutanedioic b. C44 céch tén céng déu cho 1 san phim duy nhét acid (2R)(3S}-2,-dibromobutanedioic &. Cling trong ty co ché Ar nhug sin phim la: (E)-2,3-dibromobut-2-ene, Bai a.Ta 06: ~ vy =k{RCI] > phan mg thé don phan tir Sy', trudng hop thuan Igi 1a halogenide bac II] nhu (CHs):CCL = v= k{RCI][OH"] > phan img thé lung phan tit Sy’, trudng hop thudn Igi 14 halogenide bac T nhu CHsCH,CH,CI b. Phan ting theo Sy! , ma giai doan (1) a giai dogn chim quyét dinh téc d6 phan tg va biéu thite téc d6 phan mg khéng phy thuge [CHsCOO7] nén ting ndng 44 CHyCOONa khéng lam thay 461 téc dé phan tng. — —+ Copyright © 2009 wena com aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc Ra le a a ee Bai 10: a. San phim phan img cH; chy ° ee 2-Metylpropen (x) 2-Metylptopen (Y) Phan tng qua 2 bude: Bude thit nhdt gbm trong tic gitia hai phan tir trong moi trudng acid: cH, HCH; cH, yc gee 21,c—C=CcH, cH; H 2,4,4-trimetyl pent-I-en ~ ir Wc —C—c=C —cHy cH; 2.,44-trimetyl pent-2-en Bude thi hai hydro hod Q va Z CH, HCH Hy Gh gs Mat me—F—g—4 —cth ch How Hy Cs cn, aio Znills0) Ry + O—=CH, H u H e [pn RsHC=0 + CHCOCH, eae ee OR Copyright © 2009 woman com aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc te ae meee ee Se ee oe a, Phan img sau khéng ding 4é tng hop tert-butyl propyl ether. CHsCH;CH;ONa + (CHs),C-Br —3€> (CHy)\C-OCH;CH,CHy Natri propoxide tert-butyl bromide tert-butyl propyl ether. Do phan img thé Sy’ khong thyc hign véi alkyl halogenide bac ba 'b, Ion Alcoholate 1a mét base manih, dé la téc nhan nucleophile nén phan img tich chiém wu thé nén san phim chinh cia phan ting nay la san phim tach E> a Andis “4 i 3 s CH,CHCHONa + H-C*C—Cl = a + NaBr + CH,CHACHLOH ¢. Phuong phap téng hgp higu qua 1a diing phan ti phan img Sy? cé nhém alkyl it edn tro hon va, alcoholate can tré nhiéu hon: 1g j a H-C-C-ONa + CH,CH,CH,Br Sx, CH,CH,CH,O-C—CH, + NaBr H CH; cH, Bai 12: Bai 13: a, Giai thich cfu hinh A, B = Do phan img cng LiAIHs la phan img cng trans nén A Ia trans—But-2-ene. - Do phan img cng Hy xe téc Pd/CaCOs la phan img cOng cis nén B 1a cis-But-2-ene. b, CochéchuyénhéaA B = Bbng phn hoa vi tri — a Copyright © 2009 woman com aBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc mae Se a or ee Se CH, Vi . CH pa eee a + cH, i cH a / \ +H on Nay Hw oF ‘cH, - Déng phan héa khong gian Hai cation trung gian hinh thinh khi protone héa A vi B li dng nhét nén c6 thé chuyén héa A ‘thanh B va nguge lai. @) cation trung gian @ Bai 14: Khi dun néng 2-methyleyclohexane—1,3-dione véi but-3-ene-2-one trong dung dich kiém ngudi ta thu duge mét hop chat hétu co (san phdm chinh) 6 céng thite C),HiaO> Bai 15: Co ché phan img a. Phan img xay ra qua 4 bude + Bude 1: Tao carbocation (CH,),C-OH +H” <=*(CH,),C-0'H, =H, ),C - Buée 2: Tao isobutene va isobutane — a Copyright © 2009 wosmieahoe com aBai tap Héa Hifu Co — Tai liéu danh cho sinh vién cac trudng Dai hoc wae ea Sake So ees a a ee ee CH, caw | cH, va NL 5 CH, hd A -y lia ace = + CH-C—H cure C J be. i cH, cH, = Bue 3: Tao carbocation trung gian cHh Ci ct C J CH, - Buée 4: Tao san phim J CH, /CH; 7 cH, 3 Be cay \ A _ = [ ‘oh tow Sy CH, CH, b. Néu thay bing p-xylene thi phan ting theo co ché Sp théng thudng vi su ldy ion hydride tir nhom. methyl Ia kh6ng thé duge, Sin phim la lotthotthottHotthotthotthotthott toot ttosttostttostttostttostttost*tostttos + hie ie eee OR .- Copyright © 2009 vlsnil ahem a atoBai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc ae ae oe ke Part 4 ALKANE, CYCLOALKANE 109s Bai 1: Tinh nhigt phn img AH cho cée phan tig sau day: a. (CHs)sCH + F: > (CHs)sCF + HF €. (CHs)sCH + Bry > (CH,)sCBr + HBr. b. (CHs)sCH + Cl, > (CHs)sCCI + HCL 4. (CH:)sCH + Ip > (CH5)sCI + HL ‘Cho biét cdc gid tri nding lugng phan ly lién két (Keal/mol): (CHs);CH = 93,60 (Cib)sCF 110,64 HF 135,84 Fy = 37,20 (CH)CCL = 8136 HCL = 103,68 coy 58,32 (CH;)CBr = 67,44 HBr = — 87,60 Bry = 46,32 (Cib):CI 52,32 ML 71,29 b = 3614 Bai 2: Hoan thinh céc phuong trinh phan img sau day: a, CHyCH3CH,CH)CHs + 0; —> @. CH,CH:I + HT => 'b, CHyCH;CH,CH;CH; + HNO; —> e. CHyCH.C(-O)CH; 2 ¢. (CHs),CH-Cl + Na —> f. CHyCH,CH(CH3)2 + Br: > Bai 3: Cho biél sin phim tgo thanh khi dun néng hén hgp khi CHs1 va HI. Trinh bay co ché va tinh todn gid tr) AH cho timg giai doan, Biét cdc gid trj phan ly lién két (Keal/mol): 1-1 = 36,24 ; CHs-H = 105,26 ; M-= 71,29 ; CHI = 87,17. Bai 4: Viét qué trinh phan img Br héa cdc chat sau voi sy cé mat ciia benzoylperoxide a, Isopropylbenzene. b.p-chlorotoluene. Bai 5: Cho isopentane tc dung véi Cl, (nh sing hv) thu duge 4 sin phm véi thanh phan ti 1g nhwr sau: 1-chloro-2-methylbutane (30%), 1-chloro-3-methylbutane (15%), 2-chloro—3-methylbutane (33%) va 2-chloro-2-methylbutane (22%). a. Cho biét san phim nao dé hinh thanh hon, giai thich. b. Tinh kha nang phan img tvong déi cua cde nguyén tix hydro giin véi carbon bée I, I, IIL Bai 6: Viét co ché phan tmg ciia 2-methylpropane va CCl; durge thye hign & 130+140°C véi sy 06 mat cua tert-butylperoxide, — a Copyright © 2009 wosmileahoe com ietap Héa Hifu Co — Tai Ii — he ae Tit eyclopropane, 1u danh cho sinh vién cdc trudng Dai hoc ee a es ee 3-dimethylbutane, feu ché ai 8: Kha nang phan img twong 46i cua cée hydro bac 1, Il, IH d6i véi phan img chloridize (phan img Cl ha) 1a 1:3,8:5 tuong img. a, Tinh lugng twong déi cia monochlorobutane nhdn dge khi Cl héa n-butane b. Tinh phan trim cia cdc san phim kha nhau. ¢. Tinh phan trim céc sin phim monochlorated (durge Cl héa mot Lin) khi Cl héa 2-methylbutane. Bai 9: Nguoi ta chuyén héa 100 g CII, thanh CHCl véi higu suit 18 40%, Sau d6 cho todn b6 hong CH,Cl vita tgo thanh tée dung véi Na dé thu ethane (Higu sudt 50%). Sau dé ngudi ta Br héa ethane, sau bi phan ting két thi thdy thu durge 60% bromoethane, Tinh lugng bromoethane sau phan img Br héa. Bai 10: Tir isoamyl chloride, hay viét so dd diéu ché 2,3,4,5tetramethylhexane. Bai 11: Viét cng thite céu tgo cia céc hyp chit sau: a, 2,6-dimethylspiro[4,5}decane b. 1,4-dimethylspiro[2,2}pentane. © Spiro[4,4Jnonane. 4. Spiro[3,4Joct-1-ene. €. Bicyelo[3.2.1Joctane. f. 2,3-dimethyl-9-isopropylbieyclo[5.3.0]decane. Bai 12: Tir hgp chat c6 3 nguyén tir Carbon, viét phuong trinh tong hgp bicyclo[4.1.0Jheptane. Bai 13: Hoan thanh céc phyong trinh phan dmg sau va cho biét trong mdi phan img, chat nao 1A chat trung gian hoat dng. Goi tén loai phan tg: a Cl SH: + CH:N2 > b. CHyCH=CH + CHal; —“# > fu tric Bai 14: Vid ng thire \¢ sin phdm ciia cde phan img sau: a, 2-methyleyclopent-I-ene + CHC —S2° 4 A =B. b. I-methyleyclopent-I-ene + CHCIBrz > C+D. Bai 15: Cho n-butane phan img véi Cl; theo ty If 1 : 1 e6 ehiéu séng thu duge hén hgp A va hn hop khi B. Dé hap thy hét khi HCI trong B can vita dit 1,6 1 dung dich NaOH 1,25M, a, Viét phuong trinh phan tmg thé cia n-butane véi Cl (I : 1) va néu eo ché phan img. b. Tinh khdi Iugng hén hgp A. ¢. Sin phim chinh trong phan img thé 6 trén chiém 72,72% khdi Iugng hdn hop A. Tinh khdi lugng cita san phim chinh va phy. d. Hay cho biét nguyén tir H 6 nguyén tir carbon bae II tham gia phan img thé véi Cl: dé hon nguyén tir H 6 nguyén tt carbon b§e Ibao nhieu Lin ee eee = Copyright © 2009 wosmileahoe com ieBai t8p Héa Hifu Co — Tai liéu danh cho sinh vién cdc trudng Dai hoc ee al ed BAi 17: Phan img gitta spiropentane véi Cl c6 chiéu sing 1A mét phuong phap dé diéu ché Chlorospiropentane (mot sin phim monochlorated): ><] + Hel D<] + ch MS a. Giai thich tai sao phan img trén thudng duge sir dung dé digu ché chlorospiropentane. b. Néu cé san phdm dichlorated (san phim Cl héa 2 lan) tao thanh. Hay néu phuong phap tich hai san phim 46. ©. Trinh bay co ché phan ing CI héa trén, BAi 18: Cho so d6 sau: i Bay Mg B xt AA > Az As 2 Ay os o ceethan ea00C a cen fcr 1500°C_ HMA By fas Ljp pp, By Cao su isoprene lant w 1" Jeon 4 Br (Fe Bry /as DE, pg 2: 5 (san phim cain) 180, 1 Da (sia phim chink) a, Viet cac phyong trinh phan img theo so 46 chuyén héa trén. b. giai doan chuyén Bz thin Bs, trong diéu kign c6 rat it Br, ngoai Bs nguéi ta cn thu duge mot lugng nhé alkane By khée. Hay xéc dinh B, va giai thich sy tao thinh By Bai 19: Hoan thanh so dé phan img sau: po D Acetone AB L5G — 1A-dibromebur-2-ene 550-600 av bute EOE | PB Cr Dy Glyceryl trinitrate sa 1 BeTeH, Me RS Wierkie’ C25 qggr D2 isoamylacetate Trong so d6 trén: Cac chat A, A), B, By, Bz...D2 déu la céc hgp chat hitu co. Bai 20: Tir cyclopropane va cée chit vé co thich hyp, viét cde phuong trinh phin img dé diéu ché cée chit sau: a. Diphenyl b. Teflon (CF:-CF2)p OPER H RO HEROES HERD HERO HERO HH OGst tastes taste ost st ost test tts A Copyright © 2009 woman com aTinh nhigt phin img AH (Keal/mol): a. (CHs)sCH + Fp > (CHh)sCF + HF AH =115 (Keal/mol) 1b, (CHs)sCH + Cl, > (CHs):CCl + HCL AH = (Keal/mol) ©. (CHs);CH + Br: > (CH3)sCBr +HBr AH = ~15,12 (Keal/mol) d. (CH3)CH + > (CHs)sCI + HT AH = 6,24 (Keal/mol) : Hoan thanh cée phyong trinh phan tg: a. CO; +120. b. CHsCH;CH(CH3)NO», CHsCH;CH)CH.NO;, € (CHy):CH-CH(CHs)2 d. CH;—CHs. CHsCHCH:NO2, CHsCH)NO2, CHsNO> e. CHsCH3CH,CHs. f. CHs-CH-[(Br)C(CHs) CH. Co ché timg giai doan va higu img nhiét phan img: CH,I “> CH, + I 1, CH, + HICH, +f ; AH= 71,29~105,0=~33,71 (Keal/ mol) 2. 1+ CHI—r H, ; AH= 57,00-36,00 21,00 (Keal/mol) © Céng (1) va (2) ta duge phan tmg: CHsI + HI —> I: + CH, ; AH= 12,71 (Keal / mol) Bai 4: a, Tacé cae qua trinh 38,000, —6u.c00n, H,CH(CH, ), 8 COOH, H,C(CH), + By —> CH,CBR(CH,),+ Be CHCHICH), + B —> CH ClCH), + Hr H,C(CH,) + Bry. —> C,H,CBr(CH,), + Br b. Co ché tong ty cdu a. Bai S: a. 2-chloro—2-methylbutane dé tao thin nhit vi trong phan img thé géc Sp, géc ty do cdng bén thi san phdm cng wu tién, ma gc (CH,), CCH,CH, cé electron ty do nim trén carbon bac IIT nén ban nhit. Vi vay sy két hgp cia géc Cl v6i gde (CH,), CCH,CH, 14 dé xdy ra nh b. Kha ning phan img twong déi cia cée nguyén tir hydro gin véi carbon bac I: bée II: bac IIT tuomg img ty 1é: 13,3: 4,4. + — ae ZA Copyright © 2009 volemttl@yahoo.com.vn 2(Me,CO), — ——+ 2Me,CO* Me,CO" + Me,CH—> Me,COH + Me, Mec + CCl, > Mey CCl, + Me,CH CHCI, + Me,C* cl + cel, (Qué trinh phat trién day chuyén cho dén khi cdc géc ty do gp nhau => xdy ra sy ngdt mach. Bai 7: Digu ché Cyelopropane > CH,CH,CH, Br—"" 5 CH,CH = CH, > CH,CHBrCH, —* 9 sin phim. Bai 8: a. C6 6 nguyén tir H dé hinh thanh I-chlorobutane (A) va 4 H dé hinh thinh 2-chlorobutane (B). Ty 1g nguyén tir ctia H (1): H (ID 1a 3 : 2. Luong twong déi cua san pha la: (A)=3 x 1=3 va (B)=2 x 38-76 Phan trim (A) va (B) la %A= 100% = 28% %B= © x100% = 72% 106 ¢, C64 san phim monochlorated khac nhau: 1-chloro—2-methylbutane (C) 2-chloro—3—methylbutane (E) 2-chloro—2-methytbutane (D) 1-chloro-3-methylbutane (F) Ta e6 lwgng tuong déi va % ede san phdm a: chit Lugng tong ai Phan trim 100% = 28% © 21,6 5 <> x100% = 23% (oy 6 1.6 : x 3.85 ES 100% ~35% © 2x38=7.6 ae 3 100% =14% ® 3x 153 100% = 14% 216 KOWiakotel EB, Me CH, GH-CHyCHy Cl CH CH-CH = Cl, “> CH CH- CHEB “CH; CH-CH-CE-CE-CH CH; CH, CH; CH, CH; CH,CH,CHy + <= a ee et = ZA Copyright © 2009 volemttl@yahoo.com.vn 2Bai tp Héa Hifu Co — Tai ligu danh cho sinh vién cdc trudng Dai hoc Reem te ae ee ee i Se Bai 11: Viét cng thie edu tao: HC. CH, (@) (b) © Hy fis cH Jn Nou ve CH, CH @) © (o) Bai 12: Br(CH, ), Br» HOOC(CH, ), COOH“ » HO(CH,), OH Br(CH, ), Br 8 soci) ), COOH S44 5 C,H,OOC(CH, ), COOC,H, — 5 mote a ott Coit) (> COOCH, Bai 13: = (a) cyclopropane ; (b) methyleyclopropane. - Chat trung gian hoat dng ciia phan tng: (a) li carbene :CH,, (b) la carbenoid ICH,Znl (tién chat cita carbene :CH2). - Logi phan img nay la: Phan tg eng hop déng vong. Bai 14: cng hgp cis vio C = C, nhumg két qua 1a ving ba canh c6 thé & vi tri cis hode trans véi tnhém CHs dé tao (A) hode (B): cl a cl a H i (A) (B) —— en a Copyright © 2009 wai aahoe comin %Bai tp Héa Hifu Co — Tai ligu danh cho sinh vién cdc trudng Dai hoc ee a oe ee a i Se — e- b. Anion CIBmC: duge tao thanh sé mat Br” cho carbene CIBrC: ; carbene ny cOng vio C= C va Cl hode Br sé 6 vi tri cis so v6i hom CH dé duge (C) hoge (Dy Br «1 cl ‘Br CH; CH, © (D) Bai 15: a. Phuong trinh phan tmg: askt s-CH)-CH-CH; + on CH+CH-CH-CIbC1 (¥) + HCL Ca ché phan img la co ché thé géc ty do Sg: sin phim chinh la (X), sin phdm phy la (Y). (CHs-CH)-CH(CI)-CH (X) + HCL b. my = 1,6%1,25%92,5=185 ¢, Khéi hrgng méi san pl m, —185%72,72 «100 d. Goi kha nang phan img thé béi Cl, cia m6t nguyén tir H lign két véi nguyén tir carbon bac II la a, =134,532g;my = 185-134,532 ~ 50,468g bac 11a b ta 6: 4a 4a+6b 100 = 72, 72.=> 109,12a = 436,32b = a, My = Mp = 165,25 = 84 gimol => A va B la déng phan cia nhau (vi déu la cycloalkane). Goi CTPT ciia A, Ba CH, (x23;6Sy S2x)=> 12x ty 84 => CTPT cita A, Bla CoH - Khimono-Cl héa B thu duge mét hyp chat duy nhat = B la cyclohexane, - Khi mono-Cl héa A thu duge 4 hop chat => Vi vay A cé thé 14 methylcyclopentane hodc A 18 iso-propyleyclopropane. b. Cu dang (gh8) bin nhat cia sin phim mono-Cl héa tr B li e-chlorocyclohexane H H A i cl u H H H H ———- eb 2 wae OR Copsriche 8 2000 talomlasabms oon ta &Bai tp Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc meee Se ae ee es - e- Bai 17: Bai 18: _—— Copsrich 8 2000 tolsmlasabasoonta B Do cu tric ciia spiropentane [a d6i ximg, cde nguyén tir H trén nhém methylene déu nhu nhau, do d6 phan img mono-Cl héa cd thé xy ra trén bat cit nhém methylene nao. Tach bing phuong php chung edt phan doan vi san phdm mono-Cl héa c6 nhiét d6 sdi thap hon sin phim di-CI héa, Phan ing xay ra theo co ché thé géc ty do Sp. Hoan thanh so dé phan tng: (1) CaHp > CHsCH=CH) + CH, 2 @) CHsCH.CHs + Br; > CH;-CHBr-CHs + HBr CH; + Hp "5 CH,CHAC (4) CHy-CHBr-CH; + Mg #8 5 (CHs),CH-MgBr (5) (CHs):CH-MgBr + CH
C1 OCH;-CH=CH, + 2H (7) n CHj=CCH-CH=CH; —““> (-CH,-CCH;=CH-CH), (8) 2CH, SYS HC = CH + 3H, (9) HC=CH+2H, ““ >CH, -CH, (10) CHy. Br, —“45 CH,CHBr+ HBr (11) 3HC = CH" 5 CoH (12) CoHe + CHy=CH-CH; — > Calls-CH(CHs)a (13) CeHs-CH(CHs)2 + Bh > p-BrCeH-CH(CH)2 + HBr (14) p-BrC6H,-CH(CHs)2 + Bry “> p-BrCgH.-CBr(CH3)2 + HBr (15) CHs-CH(CHs)2 + HNO; "8°"? p.O;NC¢Hy-CH(CH,): + HO B, la n-butane Tao thanh Bg la do phan img thé géc ty do Sg cia C)Hy voi Bry nhu sau: () Br-Br —> 2Br° (2)CH,-CH, + Br’ > CH,-CH? + HBr CH, -CH + Br, > CH,CH,Br + Br’ CH,-CH, + Br’ > CH,-CH} + HBr. (3) CH, Br’ > CH,CH,Br Br’ + Br > Br, CH, ~CH} + "CH, ~CH, > CH,CH,CH,CH, eeBai t§p Héa Hifu Co — Tai ligu danh cho sinh vién céc trudng Dai hoc ae ie a eR ee ee Bai 19: chat ‘Céng thie cdu tg0 Chat Céng thire cau tao A CH=CH By CH,=CH-CH,CI B C.H,0H C1 CICH,-CHOH-CH,CI c CHSCHO D HOCH-CHOH-CH,OH D CH;COOH By CHs-CHCL-CH G CH:=CH-CH-CH; Q (CHs):CHMgCl A CHsCH-CH: Dy (CHs):CHCH:CH;OH Ngoai ra C14 CHsCOOH thi D la (CHsCOO),Ca Ala CH thi Bla HC = CH, Cla CHsCHO... a cH, 2 9C,H, GE C,H, 4 cyclohexane +2 > methyleyclohexane — St» phenyleyclohexane—“ > diphenyl b. HC=CH C,H, 5¢,Cl, 22> CCI, - CC, 25 CF, = CR, 82 teflon OER HERO ERO HERO HERS HERO HERO HR ast rag pO Op ag gH ast tt ght Part 5 ALKENE, ALKINE, DIENE, TERPENE 1: Hoan thanh cée phuong trinh phan ting dui day va biéu dign dng phan I§p thé cia cde sin phim tao thanh bang céng thite chiéu Fischer. a, cis-but-2-ene + Bro > fe. Acid fumarie + Bry > b. trans-but-2-ene + Br2—> 4. Acid maleie + Bry > ‘Bai 2: Phan img sau cho san phim 1a hgp chit mesomeric hay bién thé racemic’ trans—3,4-dimethylhex-3-ene +H, “> san pha, Bai 3: Cho biét san phdm tgo thanh khi ozone héa cdc hop chat sau day: a, CHsCH=CHs, b. CILCILCH(CHs)-CH=CIt, ¢. I-methyleyelohexa—I 4diene. Bai 4: Vist cdc qua trinh a8 dig ché: a, CHsCH,COCH(CHs)s tir propene, HCl, Mg, BHs, Hz02, NaOH, CrOs. b. Cyclopentanone tir eyelobutene, Os, Zn/CHyCOOH, LiAIHy, PBr;, Mg, HCOOCHS, CrOs, Hee ee Cosrigh © 2000 talsmlasabmsoonamn é