Gi tn thay th ca hp cht hu c.

1. Cc khi nim. Trc tin chng ta cn lm r mt s khi nim. Ni dung trnh by di y khng c mc ch nh ngha chnh xc m ch c mc ich lm cho cc bn hiu c n l ci g, tc l hnh dung c khi nim. 1.1. Lin kt sigma v lin kt pi. Lin kt sigma () l kiu lin kt bn nht trong cc lin kt ha hc. Lin kt sigma c hnh thnh t s xen ph trc gia cc orbital s+s, pz+pz, s+pz. V d nh trong phn t metan (CH4), tt c cc lin kt trong phn t u l lin kt sigma. Lin kt pi () l kiu lin kt km bn vng, d b ph v trong cc phn ng ha hc. Lin kt pi c hnh thnh t s xen ph bn gia cc orbital p. V d nh trong phn t etilen (C2H4), ti lin kt i, ngoi lin kt sigma gia hai nguyn t carbon, cn c lin kt pi c hnh thnh do s xen ph bn gia 2 orbital p. 1.2. Nhm th v nhm chc. Nhm th l mt nguyn t hoc mt nhm nguyn t th vo ch nguyn t hydro trong mch carbon. V d nh nhm ankyl, ankenyl, ankynyl, cc halogen, nhm amino (-NH2), nhm hydroxyl (-OH), Nhm th Hu t Ankyl Ankenlyl ankylyn halogen R-X Flo/clo/brom/iod nitro R-NO2 nitro amino R-NH2 amino amin Trong bng trn, 3 nhm th u c thnh lp t vic b i mt nguyn t H ca ankan, anken hoc akyn, v phn ny, cc bn c th tham kho mc 3.3. Cc nhm th sau l mt s v d khc. V cn nhiu nhm th khc na. cc bn c th xem chi tit mc 2.2.2, v bng 4. Nhm chc l mt hoc mt nhm nguyn t hoc cc lin kt bi c trng cho tnh cht ca phn t mang n trong cc phn ng ha hc. Cc hp cht hu c mang cng nhm chc s c tnh cht ha hc tng t nhau, nhng thng s c mt vi s khc bit nh do nh hng ca mch carbon hoc cc nhm th khc. Chng ta s tm chia nhm chc thnh 2 loi, l nhm chc lin kt (bao gm ni i v ni ba) v nhm chc nhm nguyn t. 1.3. ng phn. Cc hp cht hu c c cng cng thc phn t gi l cc ng phn ca nhau. C th chia lm 2 loi ng phn: ng phn cu tao v ng phn hnh hc. 1.3.1. ng phn cu to. Cc phn t hp cht hu c c gi l ng phn cu to ca nhau nu chng c cng cng thc phn t nhng khc nhau v trt t sp xp trong phn t. 1.3.2. ng phn hnh hc. Nguyn Tin t KSTN TVT K54 - HBKHN 1 Bng 1: mt s nhm th hay gp Cu trc Tin t RAnkyl- (v d etyl)

Cc phn t hp cht hu c c gi l ng phn hnh hc ca nhau nu chng c cng cng thc phn t, ging nhau v trt t sp xp nhng khc nhau v cch b tr cc nguyn t hoc nhm nguyn t trong khng gian. C 2 kiu ng phn hnh hc l cis/tran v E/Z. Trong chng trnh ph thng, chng ta ch tm hiu kiu ca ng phn hnh hc l cis/tran, khi m cc nhm th nh vo cc nguyn t C ca ni i l ging nhau (v d buta-1,3-dien). 1.4. Phn loi hp cht hu c da vo cu trc mch cacbon. Nu da trn kha cnh l s khp kn ca mch cacbon, chng ta c th chia hp cht hu c lm 2 loi: mch h v mch vng. Nu xt da trn kha cnh cc nhm ankyl gn vo mch chnh, ta c th chia hp cht hu c lm hai loi l mch thng v mch phn nhnh. Cn nu xt trn kha cnh mc bo ha lin kt trong phn t, ta c th chia hp cht hu c lm hai loi l hp cht no v khng no. 2. Cch gi tn tng qut hp cht hu c. Mt hp cht hu c c th c nhng loai tn goi sau: Tn thng thng (common name): l nhng tn c gi theo lch s. Tn h thng (system name): l nhng tn gi c quy tc nht nh. - Tn gc chc. - Tn thay th. 2.1. Tn gc chc. Tn gc chc = tn gc + tn chc. Vic gi tn gc chc s c tm hiu trong tng bi hc. Trong ti liu ny, ch gii hn vic gip cc bn c k thut gi tn thay th cc hp cht hu c. Tuy nhin, t cng thc chung trn, chng ta cng phn no cng c th hnh dung ra cch gi tn gc chc. 2.2. Tn thay th. Tn thay th ca hp cht hu c c th c chia lm 5 phn nh sau. c tnh ng Tn phn th Tn mch cacbon Kiu lin kt Nhm chc (phn ny c phn hnh hc chnh (phn ny chc (c th c hoc
(phn ny c th c hoc khng) th c hoc khng) (phn ny chc chn c) chn c) khng)

2.2.1.

2.2.2.

Di y, mnh s trnh by c th cho cc bn c im ca tng phn trn. c tnh ng phn hnh hc. xc nh c c tnh ng phn hnh hc (nu c), chng ta cn thc hin cc bc sau. Xc nh c ni i trong phn t khng? Xc nh xem hai nhm th nm v cng mt pha ca ni i hay khc pha i vi ni i trong phn t. Nu cng v mt pha th ta c ng phn cis, nu nm khc pha ca ni i th ta c ng phn tran (c th nh nh sau: cis-cng, tran-khc). Tn phn th. Sau khi xc nh c nhm chc v mch cacbon chnh, cc nguyn t hoc nhm nguyn t khc u c xem l nhm th. Di y l tn mt s nhm th thng dng. Cng lu l cc nhm th c trnh by trong bng di y khng nhm no u tin hn so vi nhm no m bnh ng vi nhau nu trong mch c nhiu nhm th khc loi c nh vo. Nhm ankyl.

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CH3 CH3CH2 CH3CH2 CH2 CH3(CH2)2 CH2 CH3(CH2)3 CH2 CH3(CH2)4 CH2 CH3(CH2)5 CH2 CH3(CH2)6 CH2 CH3(CH2)7 CH2 CH3(CH2)8 CH2 CH3CH2CH2 (CH3)2CH CH2 = CHCH2 CH2 = CH C6H5 C6H5CH2 CH3CH(C2H5) (CH3)2CHCH2 (CH3)3C -

metyl etyl propyl butyl pentyl hexyl heptyl octyl nonyl decyl propyl isopropyl/1metyletyl anlyl/prop-2-enylvinyl/etenyl phenyl benzyl sec-butyl/1metylpropyl isobutyl/2metylpropyl tert-butyl/1,1dimetyletyl

Nhm halogen. F/Cl/Br/I flo/clo/brom/iod - Nhm nitro. NO2 nitro 2.2.3. Tn mch cacbon chnh. Chn mch chnh l mch cha nhm chc v di nht. Tn ca mch chnh c xc nh da trn s nguyn t cacbon trong mch. Cc bn c th tham kho bng 2 di y. Bng 2: tn mch chnh cho mch c t 1 n 10 nguyn t C 1 2 3 4 5 6 7 8 9 10 MetEtPropButPentHex- HeptOctNonDecM em Phi Bn Phn ha Hc ngoi ng 2.2.4. Kiu lin kt. Kiu lin kt n: an Kiu lin kt i: en Kiu lin kt ba: yn Nu c hn mt lin kt i hoc lin kt ba trong phn t, ta dng cc tin t ng trc: C 2 lin kt: di. C 3 lin kt: tri. C 4 lin kt: tetra. C 5 lin kt: penta. C 6 lin kt: hexa. V d: dien, trien, Nguyn Tin t KSTN TVT K54 - HBKHN 3

2.2.5. Nhm chc. Trong mt hp cht hu c, c th c mt nhm chc (s lng nhm c th l mt chc n chc hoc nhiu chc a chc), c th c nhiu nhm chc khc nhau (tp chc). cc bn c th tham kho bng 4. 3. Gi tn ankan v cycloankan. Ankan v cycloankan l hp cht tng i c bn, ch gm cc lin kt n trong phn t. Cch gi tn cc hp cht hu c khc tng t nh vic gi tn ankan v cycloankan. V vy, nm c cch gi tn ankan s gip chng ta d dng trong vic gi tn cc hp cht hu c khc. Mc ny s trnh by cch gi tn hp cht hu c no l ankan v cycloankan. 3.1. Gi tn ankan mch thng v cc cycloankan c bn. Sau y l tn gi ca 10 ankan u tin v 4 cycloankan c bn. Bng 3: tn gi ca cc ankan mch thng v cycloankan khng phn nhnh. ankan Cycloankan Cng thc Tn gi Cng thc Tn gi CH4 metan CH3CH3 etan CH3CH2CH3 CH3(CH2)2CH3 CH3(CH2)3CH3 propan butan pentan
CH2 H2C H2C CH2 CH2

Cyclopropan Cyclobutan Cyclopentan

CH2 CH2 H2C CH2

CH2 CH2 CH2 H2C CH2

H2C

CH3(CH2)4CH3

hexan

H2C

CH2

CH2

Cyclohexan

CH3(CH2)5CH3 heptan CH3(CH2)6CH3 octan CH3(CH2)7CH3 nonan CH3(CH2)8CH3 decan Trong vic gi tn di y, phn th c hiu l cc nhm th trong bng 1. 3.2. Gi tn cc ankan v cycloankan phn nhnh. gi tn ca cc ankan v cycloankan cng nh cc dn xut phn nhnh, ta tin hnh theo cc bc sau: Bc 1: Chn mch chnh. Chn mch chnh l mch di nht. T , xc nh tn ca mch chnh theo bng 2. Nu c hai hoc nhiu nhnh c cng chiu di (cng s C) th chn mch no c nhiu nhnh nht lm mch chnh. Trong hp cht mch vng no, vng no c xem l mch chnh ngoi tr khi mch cacbon nh vi vng c chiu di thng ln hn mch vng. Tin t cyclo c thm vo trc tn mch cacbon to thnh tn mch chnh. Cc quy tc trn c m t nh hnh 1 di y. Nguyn Tin t KSTN TVT K54 - HBKHN 4

Bc 2: nh s ch v tr. i vi mch h, ta nh s ch cc v tr t u mch cacbon gn nhnh nht. Nu trong mch cacbon c 2 nhm th gn 2 u mch nh nhau th nh t u m tng s ch cc nhm th l nh nht. i vi mch vng, ta nh s ch t nguyn t C gn vi nhm th. Nu trn vng c nhiu nhm th nh vo th vic nh ch s cc nhm ankyl s c bt u theo th t bng ch ci, tc l nu trn vng c c nhm etyl v metyl th chng ta s nh ch s 1 vo v tr cacbon gn nhm etyl. Vic nh ch s s i theo chiu sao cho tng s cc ch s l nh nht.

Bc 3: xc nh v tr, tn v s lng ca cc nhm th gn vo mch chnh da vo mc 2.2.2 hoc da vo mc 3.3 di y. Bc 4: ghp tn li theo th t sau: ch s th hin v tr ca nhm th, tin t th hin s lng nhm th ging nhau (i, tri,), tn nhm th, tn mch chnh, hu t -an. Nu c nhiu nhm th th sp xp cc nhm th theo th t bng ch ci, v d etyl trc metyl trc propyl, vic sp xp ny khng ti cc tin t di, tri, tert, sec nhng li quan tm ti cyclo v iso. Nguyn Tin t KSTN TVT K54 - HBKHN 5

3.3. Xc nh tn cc ankyl phn nhnh. Mt s ankyl n gin mch thng v mt s ankyl mch nhnh n gin nu mc 2.2.2. Tuy nhin nhiu lc sau khi xc nh xong mch chnh, xut hin cc nhm th ankyl phn nhnh phc tp. Ni dung mc ny s hng dn bn xc nh tn ca cc nhm ankyl phn nhnh khi cn thit. xc nh tn gi ca cc ankyl, ta tin hnh theo cc bc di y: Bc 1: xc nh chui di nht ca nhm th ankyl bt u t nguyn t C gn vo mch chnh. T , xc nh c tn gc ca nhm ankyl. Bc 2: xc nh v tr ca cc nhm th ca mch ankyl. Bc 3: gi tn nhm ankyl.

V d gi tn hp cht sau:

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3.4. Mt s hp cht khc lin quan. Ngoi cc nhm th l ankyl, cn cc nhm th khc l cc nguyn t halogen (Cl, F, Br, I), nhm nitro, Cc nhm th ny l bnh ng nhau, khng ci no c u tin hn ci no. Trong mch vng, chng ta s nh ch s bt u t nhm th c ch ci u ng trc nht trong bng ch ci. Cng nhc li l vic sp xp ny khng ti cc tin t di, tri, tert, sec nhng li quan tm ti cyclo v iso.

4. Gi tn cc hp cht hu c cha nhm chc lin kt (hidrocacbon khng no). Vic gi tn cc hidrocacbon khng no (cc anken, ankyn, ankadien,) tng t nh gi tn ankan, ngoai tr mt s im: Chn mch chnh l mch di nht m cha cc lin kt i hoc lin kt ba. Tin hnh nh ch s t u mch chnh gn vi ni i hoc ni ba nht. sau , xc nh v tr cc nhm th ankyl trn mch chnh. Trng hp mch c ni i v ni ba cng cch hai u mch chnh mt khong nh nhau th nh s t u gn ni i hn (do ch e trong en ng trc ch y trong yn ca bng ch ci). Nhng khng nn hiu nhm l ni i u tin hn ni ba. Hai ci ny bnh ng vi nhau. Xc nh dng ng phn hnh hc i vi lin kt i, t , xem xt vic dng tin t cishay tran-. Gi tn hidrocacbon theo th t: cis/tran, ch s ch v tr cc nhm th ankyl, tin t ch s lng nhm th cng loi, tn nhm th, tn mch chnh, ch s ch v tr lin kt bi, tin t ch s lng lin kt bi, hu t -en hoc yn. Nguyn Tin t KSTN TVT K54 - HBKHN 7

Di y s trnh by mt s v d cc bn hiu thm:

5. Gi tn hp chc hu c cha nhm chc nhm nguyn t. Cng nh i vi vic gi tn hp cht hu c cha nhm chc lin kt, trong phn t c th c mt hoc nhiu nhm chc. Tuy nhin khc vi trn, trong khi lin kt i v lin kt ba bnh ng vi nhau th cc nhm chc nhm nguyn t c sp xp theo th t u tin t cao xung thp theo bng di y. iu ny c ngha l, nhm chc no c quyn u tin cao hn s l nhm chc chnh, cc nhm chc cn li c xem nh nhm th thng thng. Bng 4: bng tm tt mc u tin ca cc nhm chc. Mc u Nhm chc Hu t Tin t (tn nhm th) tin 1 Axit cacboxylic -oic axit Caboxy2 Este -oat Alkoxycabonyl3 Amid -amid Amido4 Nitrit -nitrit Cyano5 Andehyt -al Oxo- hoc formyl6 Xeton -on Oxo7 Ancol -ol Hydroxy8 Amin -amin Amino9 Anken -en Alkenyl10 Ankin -yn Alkynyl11 Ankan -an Alkyl12 Ete Alkoxy13 Halid Halo gi tn cc hp cht ny, ta c th lm nh sau: Bc 1: Xc nh nhm chc c mc u tin cao nht. Sau , tin hnh xc nh mch di nht cha nhm chc lm mch chnh. Xc nh tn ca mch chnh. Bc 2: nh cc ch s bt u t pha gn nhm chc. Nguyn Tin t KSTN TVT K54 - HBKHN 8

Bc 3: Xc nh kiu lin kt trong mch chnh. Nu c lin kt i th thay ui an bng ui en. Cn nu c lin kt i th thay ui an bng ui yn. Bc 4: Thm ch s ch v tr v hu t nhm chc c mc u tin cao nht nh trong bng trn vo sau tn mch chnh. Bc 5: Cc nhm chc cn li c xem l nhm th. t vo trc tn mch chnh ch s ch v tr v tn cc tin t ca cc nhm th ny, ng thi sp xp theo th t bng ch ci. minh ha cho cc bc lm tng qut trn, ta i vo mt vi v d c th. 5.1. Gi tn ancol. Bc 1: tm mch di nht cha m cha nguyn t C gn vi nhm OH. T y, tm c tn mch chnh bng cch b ui an v thay bng ui ol. Bc 2: nh s ch t pha u mch gn nhm OH hn. Bc 3: gi tn. V d:

5.2. Gi tn axit. i vi axit hu c, ta c mt s lu thm nh sau khi gi tn: Nu nhm COOH lin kt vi mach cacbon h, th tm mch di nht cha nhm COOH, tn ca mch chnh v nhm chc l tn ca mch chnh cng vi hu t oic axit. Nu nhm COOH lin kt vi vng th tn mch chnh v nhm chc l tn ca vng cng vi cacboxylic axit. Tuy nhin, Vit Nam, cm t axit c chuyn ln u tn. V d:

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5.3. Gi tn cc hp cht hu c c nhiu nhm chc (hp cht hu c tp chc). Trong nhiu phn t hp cht hu c c th tn ti ng thi nhiu nhm chc. V d c th tn ti trong phn t ng thi nhm OH v gc CHO. Vy th gi tn nhng hp cht ny nh th no?. Nh ni trn, y ta cn xc nh nhm chc no u tin hn. Sau , vic gi tn c tin hnh bnh thng. di y l mt s v d cc bn hiu thm.

6. Bi tp luyn tp. 6.1. Xc nh tn gi cc cht sau.

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p n (theo th t t tri qua phi, t trn xung di): 3-etyl-2-metylhexan 4-etyl-3-metylheptan 3-metylpentan 2,2,5-trimetylhexan 4-etyl-2,7-dimetyloctan 2,3-dimetylhexan 2-metyl-5-(2-metylpropyl)nonan 5-etyl-3-metyl-5-propyldecan 1-sec-butyl-3-nitrocyclohexan 1-etyl-3-metylcyclohexan 1-cyclobutyl-2-metylpentan 6.2. V cng thc cu to cc cht sau: 4-(1,1-dimetyletyl)decan 4-(1-metyletyl)heptan 3-etyl-7-metyl-5(1-metylpropyl)undecan 4-metyloctan 2,4-dimetyl-5-propyldecan

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