ii

DANH MC CC K HIU, CC CH CI VIT TT

Vit tt Vit y

1. BTHH : Bi tp ha hc

2. xt : Xc tc

3. CTCT : Cng thc cu to

4. CTPT : Cng thc phn t

5. P : ng phn

6. ktc : iu kin tiu chun

7. GV : Gio vin

8. HTLT : H thng l thuyt

9. HS : Hc sinh

10. HSG : Hc sinh gii

11. HSGHH : Hc sinh gii ha hc

12. H : Hiu ng

13. mX : Khi lng ca X

14. nX : S mol cht X

15. p : p sut

16. P : Phn ng

17. PTP : Phng trnh phn ng

18. t0 : Nhit

19. t0nc : Nhit nng chy

20. t0s : Nhit si

21. THPT : Trung hc Ph thng

iii

DANH MC CC BNG

Trang

Bng 2.1. Tn thay th, tn thng dng ca cc axit ...... . 53

Bng 3.1. Bng im kim tra ...... 91

Bng 3.2. Bng im trung bnh ...... 91

Bng 3.3. Bng % hc sinh t im trung bnh, kh, gii ...... 91

Bng 3.4. Bng t l % hc sinh t im xi tr xung ...... .. 92

Bng 3.5. Bng tng hp cc tham s c trng ..... 92

iv

DANH MC CC BIU Trang

Hnh 3.1. th ng ly tch so snh kt qu kim tra s 1 ..... . 93

Hnh 3.2. th ng ly tch so snh kt qu kim tra s 2. ..... 93

Hnh 3.3. th ng ly tch so snh kt qu kim tra s 3 ..... . 93

Hnh 3.4. th ct so snh kt qu kim tra s 1 ...... 94

Hnh 3.5. th ct so snh kt qu kim tra s 2 ...... 94

Hnh 3.6. th ct so snh kt qu kim tra s 3 ...... 94

v

MC LC

Trang

Li cm n............................................................ ............................................. i

Danh mc vit tt ........................................................................................... ii

Danh mc cc bng .......................................................................................... iii

Danh mc cc biu ...................................................................................... iv

Mc lc ........................................................................................................... v

M U ....................................................................................................... 1

Chng 1. C S L LUN V THC TIN................................................. ....... .. 4

1.1. Khi qut v bi dng hc sinh gii trn th gii v Vit Nam................ ............. 4

1.1.1. Vn bi dng nhn tr cc nc pht trin..................................... .............. . 4

1.1.2. Bi dng hc sinh gii bc Trung hc Ph thng ca Vit Nam..... ............. .. 6

1.1.3. Tng quan vn nghin cu.................................................................................. . 7

1.2. Hc sinh gii ha hc........................................................................................ ........ ... 8

1.2.1. Khi nim hc sinh gii ha hc.................................................................... .......... 8

1.2.2. Nhng phm cht v nng lc quan trng nht ca mt hc sinh gii ha

hc cn bi dng v pht trin....................................................................... ................... 8

1.2.3. Nhng k nng cn thit ca gio vin bi dng hc sinh gii ha hc ............. 9

1.2.4. Thc trng ca cng tc bi dng hc sinh gii ha hc trng Trung

hc Ph thng hin nay................................................................................ ...................... . 10

1.2.5. Pht hin hc sinh c th tr thnh hc sinh gii ha hc........................ ............. 11

Chng 2. H THNG L THUYT V BI TP HA HC HU C

S DNG TRONG VIC BI DNG HC SINH GII............................ ....... 13

2.1. Cc chuyn ha hc hu c....................................................................... .......... ... 13

2.1.1. Chuyn 1. i cng ho hc hu c................................................... .......... .. 14

2.1.1.1. H thng l thuyt c bn......................................................................... .......... ... 14

2.1.1.2. Bi tp vn dng.......................................................................................... ......... .. 18

2.1.2. Chuyn 2. Hirocacbon...................................................................................... .. 21

2.1.2.1. H thng l thuyt c bn........................................................................... .......... . 21

2.1.2.2. Bi tp vn dng........................................................................................... ......... . 31

2.1.3. Chuyn 3. Dn xut haloden, ancol, phenol, ete................................. ............. . 36

2.1.3.1. H thng l thuyt c bn.......................................................................... ........... . 36

2.1.3.2. Bi tp vn dng........................................................................................... ......... . 41

2.1.4. Chuyn 4. Anehit, xeton........................................................................ ......... .. 46

2.1.4.1. H thng l thuyt c bn........................................................................... .......... . 46

2.1.4.2. Bi tp vn dng........................................................................................... ......... . 48

vi

2.1.5. Chuyn 5. Axit cacboxylic, este............................................................... ......... .. 52

2.1.5.1. H thng l thuyt c bn............................................................................ .......... 52

2.1.5.2. Bi tp vn dng............................................................................................ ......... 56

2.1.6. Chuyn 6. Amin, amino axit, peptit, protein......................................... ............ 61

2.1.6.1. H thng l thuyt c bn............................................................................ .......... 61

2.1.6.2. Bi tp vn dng.......................................................................................... ......... .. 66

2.2. Cc dng bi tp bi dng hc sinh gii ha hc..................................... ............ ... 70

2.2.1. Bi tp rn luyn nng lc nhn thc................................................... ............ ........ 70

2.2.2. Bi tp rn luyn nng lc t duy, tr thng minh................................ ............. ..... 74

2.2.3. Bi tp rn luyn nng lc quan st, thc hnh, vn dng kin thc.... ................ 78

2.2.4. Bi tp rn luyn nng lc vn dng kin thc gii quyt cc vn thc

tin...................................... ................ ................................................................................... 81

Chng 3. THC NGHIM S PHM................. ....... ............................................. 88

3.1. Mc ch ca thc nghim s phm...................................... ........... .......................... 88

3.2. Nhim v ca thc nghim s phm....................................... ........... ........................ 88

3.3. Phng php thc nghim...................................................... .......... ........................... 88

3.4. nh gi kt qu thc nghim......................................... ........... ................................. 89

KT LUN V KHUYN NGH...................................... ...... .................................... 97

1. Kt lun ........................................................................................................ 97

2. Khuyn ngh ................................................................................................. 97

TI LIU THAM KHO............................................... ....... ......................................... 99

PH LC................................................................................ ....... ..................................... 101

1

M U

1. L do chn ti

Chng ta ang sng trong mt th gii din ra s bng n v khoa hc v cng

ngh do s nghip gio dc v o to nc ta ng vai tr, chc nng quan

trng trong vic nng cao dn tr, o to nhn lc, bi dng nhn ti thc

hin thnh cng cng cuc cng nghip ha, hin i ha t nc v hi nhp vi

quc t, snh vai cng cc nc tin tin trn th gii. T thc t t ra cho

ngnh gio dc v o to khng nhng c nhim v gip hc sinh pht trin ton

din v o c, tr tu, th cht, thm m v cc k nng c bn, pht trin nng lc

c nhn, tnh nng ng v sng to, hnh thnh nhn cch con ngi Vit Nam x

hi ch ngha, xy dng t cch v trch nhim cng dn m cn phi c nhim v

pht hin, bi dng nhng hc sinh c nng khiu, c t duy sng to nhm o

to cc em tr thnh nhng nh khoa hc, nh qun l, doanh nhn gii v tr thnh

cn b lnh o cc cp ca ng, Nh nc.

V vy, vic pht hin v bi dng hc sinh gii mn ha hc trng ph

thng c mt v tr quan trng c bit. o to h tr thnh nhng nh khoa hc

mi nhn trong tng lnh vc. Lnh vc ha hc, trong tng lai khng xa nn cng

nghip ha cht, du kh ca nc ta pht trin vt bc, nhanh chng, nhu cu v

i ng cn b, k s c trnh k thut cao trong cc lnh vc ca cng ngh ha

hc khng th thiu. p ng nhu cu trn cn y mnh hn na vic pht hin

v bi dng hc sinh gii v ha hc trng ph thng. y cng l nhim v

tt yu trong cng cuc i mi t nc hin nay.

Thc trng ca vic bi dng hc sinh gii ha hc ang gp mt s kh

khn nh: gio vin cha chun b tt h thng l thuyt v cha xy dng c h

thng bi tp trong qu trnh ging dy; hc sinh khng c nhiu ti liu tham

kho nht l nhng trng THPT khng chuyn vic bi dng hc sinh gii

cng gp nhiu kh khn hn, chng ti chn nghin cu ti Xy dng h

thng l thuyt, bi tp phn ho hu c dng trong bi dng hc sinh gii

ho trung hc ph thng khng chuyn vi mong mun gp phn nng cao hiu

qu qu trnh bi dng hc sinh gii trng THPT khng chuyn.

2

2. Mc ch nghin cu

Xy dng h thng l thuyt bi tp c bn, nng cao phn hu c bi

dng hc sinh gii ha hc ph thng nhm nng cao cht lng dy hc ha hc

trng THPT khng chuyn.

3. Nhim v nghin cu

- Nghin cu tng quan cc vn l lun v vic bi dng hc sinh gii.

- Nghin cu ni dung kin thc ha hc hu c trong chng trnh THPT

nng cao, cc thi hc sinh gii cp tnh, thnh ph, quc gia. i su nghin cu

mt s chuyn trng tm ca ha hc hu c trong vic bi dng hc sinh gii.

- Xy dng h thng l thuyt v bi tp ha hc theo tng chuyn ca ha

hc hu c.

- Thc nghim s phm nh gi hiu qu ca h thng l thuyt v bi tp

ha hc v x l cc kt qu thu c.

4. Khch th v i tng nghin cu

- Khch th nghin cu: qu trnh bi dng hc sinh gii ha hc cc

trng THPT khng chuyn Vit Nam.

- i tng nghin cu: h thng l thuyt, bi tp ha hc v bin php bi

dng hc sinh gii phn ha hc hu c THPT.

5. Phm vi nghin cu

- Ni dung: cc chuyn trng tm ca phn ha hc hu c dng bi dng

hc sinh gii.

- i tng: hc sinh khng chuyn ha.

- a bn nghin cu v thc nghim: trng THPT Trc Ninh B, trng

THPT Trc Ninh A, trng THPT A Hi Hu tnh Nam nh.

6. Gi thuyt nghin cu

Nu xy dng c h thng kin thc l thuyt v bi tp (trc nghim t

lun v trc nghim khch quan) a dng, phong ph, c cht lng th s gip hc

sinh nng cao kin thc, rn luyn kh nng t hc, t nghin cu, ch ng v

sng to gp phn nng cao cht lng dy v hc trng THPT khng chuyn.

7. Phng php nghin cu

7.1. Nghin cu l lun

- Nghin cu cc vn bn v ch th ca ng, nh nc v B gio dc o

to c lin quan n ti.

3

- Phn tch, tng hp, h thng ha, khi qut ha cc ngun ti liu xy

dng c s l lun c lin quan n ti.

- Tng hp cc kin thc ha hc hu c cn thit cho vic bi dng hc

sinh gii ha hc.

- Su tm, phn tch cc thi hc sinh gii ha hc cc cp.

7.2. Nghin cu thc tin

- Tm hiu thc t ging dy, bi dng HSG cc lp, trng khng chuyn

hin nay nc ta.

- Trao i kinh nghim vi gio vin ha hc dy bi dng hc sinh gii ca

mt s trng THPT khng chuyn.

- Xy dng h thng l thuyt, bi tp ha hc v cc phng php s dng

trong vic bi dng hc sinh gii.

- Thc nghim s phm nhm nh gi s ph hp ca h thng l thuyt, bi

tp ha hc xy dng v cc bin php xut.

8. ng gp ca ti

- V mt l lun: xy dng c h thng kin thc l thuyt bi tp (trc

nghim t lun v trc nghim khch quan) phn ha hc hu c dng cho bi

dng hc sinh gii ha hc.

- V mt thc tin: xy dng c h thng l thuyt v bi tp ha hc c

bn, nng cao dng trong vic bi dng hc sinh gii ha hc v cung cp cho

gio vin, hc sinh yu thch mn ha hc mt ti liu tham kho b ch.

9. Cu trc lun vn

Ngoi phn m u, kt lun, khuyn ngh, ti liu tham kho, ph lc lun vn

c trnh by trong ba chng:

Chng 1: C s l lun v thc tin

Chng 2: H thng l thuyt v bi tp ho hu c s dng trong vic bi

dng hc sinh gii

Chng 3: Thc nghim s phm

4

CHNG 1

C S L LUN V THC TIN

1.1. Khi qut v bi dng hc sinh gii trn th gii v Vit Nam

1.1.1. Vn bi dng nhn tr cc nc pht trin

Vai tr ca cc nhn ti i vi s pht trin ca quc gia c xc nh

nhiu nc trn th gii. Vi nc ta, nm 1484, Thn Nhn Trung khc vo bia

t ti Vn Miu Quc T Gim dng ch: Hin ti l nguyn kh ca quc gia,

nguyn kh thnh th nc mnh, ri ln cao; nguyn kh suy th nc yu, ri

xung thp. Chn l ny c nhiu nc khng nh v ch trng trong chin

lc pht trin ca t nc mnh. Ngy nay, khi th gii bc sang giai on ton

cu ha th vai tr ca c nhn, nhng nhn ti ca t nc cng tr nn quan

trng hn bao gi ht. V vy khng c t nc no li khng chm lo n vic

pht hin, bi dng v s dng nhn ti. Tuy nhin, mi t nc, mi giai on

li c nhng quan nim v cch thc pht hin, bi dng nhn ti khc nhau.

Chng ta cng xem xt quan nim ca th gii v vn gio dc HSG.

1.1.1.1. Quan nim ca th gii v gio dc hc sinh gii

Vic pht hin v bi dng HSG c ch t rt lu. Trung Quc, t

i nh ng (nm 618 trc cng nguyn) nhng tr em c ti c mi v

hong cung hc tp v gio dc bng nhng hnh thc c bit. Chu u trong

sut thi Phc Hng, nhng ngi c ti nng v ngh thut, kin trc v vn

hc, u c nh nc v cc t chc, c nhn bo tr, gip . Chu u,

vin quc t Aurino vi nhim v nhn din, kho st HSG v HS ti nng trn

khp th gii. T nm 2001 chnh quyn New Zealand ph chun k hoch pht

trin chin lc HSG

1.1.1.2. Khi nim hc sinh gii

- Nhn chung cc nc u dng hai thut ng chnh l Gift (gii, c nng

khiu) v Talent (ti nng) ch HSG. Lut bang Georgia (Hoa K) nh ngha

HSG: HSG l HS chng minh c tr tu trnh cao, c kh nng sng to,

th hin mt ng c hc tp mnh lit, t xut sc trong lnh vc l thuyt, khoa

hc, l ngi cn mt s gio dc c bit v s phc v c bit t c trnh

tng ng vi nng lc ca ngi .

5

- C quan gio dc Hoa K miu t khi nim HSG nh sau: l nhng HS

c kh nng th hin xut sc hoc nng lc ni tri trong cc lnh vc tr tu, s

sng to, kh nng lnh o, ngh thut hoc cc lnh vc l thuyt chuyn bit.

Nhng HS ny th hin ti nng c bit ca mnh tt c cc bnh din x hi, vn

ha v kinh t. Nhiu nc quan nim: HSG l nhng a tr c nng lc trong

cc lnh vc tr tu, sng to, ngh thut v nng lc lnh o hoc lnh vc l

thuyt. Nh vy HSG cn c s phc v v hot ng hc tp trong nhng iu

kin c bit pht trin cc nng lc sng to ca h.

1.1.1.3. Mc tiu dy hc sinh gii

Mc tiu chnh ca chng trnh dnh cho HSG v HS ti nng cc nc

u hng n mt s im chnh sau:

+ Pht trin phng php suy ngh trnh cao ph hp vi kh nng tr tu

ca tr.

+ Bi dng s lao ng, lm vic sng to.

+ Pht trin cc k nng, phng php v thi t hc sut i.

+ Nng cao thc v kht vng ca tr v s t chu trch nhim.

+ Khuyn khch s pht trin v lng tm v thc trch nhim trong ng

gp cho x hi.

+ Pht trin phm cht lnh o.

1.1.1.4. Phng php v cc hnh thc gio dc hc sinh gii

Nhiu ti liu khng nh: HSG c th hc bng nhiu cch khc nhau v tc

nhanh hn so vi cc bn cng lp v th cn c mt chng trnh HSG pht

trin v p ng c ti nng ca h. Theo Freeman c hai phng php m nh

trng c th vn dng trong vic dy cho HSG l:

+ y nhanh tc hc tp ca HS bng cch chuyn chng ln hc cng vi

nhm HS ln tui hoc cht y thm t liu m chng c th hc.

+ Lm giu, m rng v o su thm cc t liu hc tp cho ngi hc.

Nhiu nc thng vn dng mt chng trnh c bit vi cch dy c bit cho

php HS hc dn, hc tt, tch hp ni dung cc mn hc hoc ghp chng trnh

mn hc ca hai, ba nm HS c th y nhanh, tt nghip ph thng sm hn

cc HS bnh thng.

6

Nh vy cc nc khc nhau c nhiu phng php v hnh thc gio

dc HSG, cc hnh thc ny rt a dng v u hng n to iu kin hc tp cho

HSG pht trin ht nng lc ca mnh. HSG cn c hnh thc hc tp khc vi HS

bnh thng pht huy c tim nng ca i tng ny.

1.1.1.5. nh gi hc sinh gii

Theo Clack, khi nh gi HSG cn tun th mt s nguyn tc sau:

- Xem xt mt cch ton din cc mn hc i vi nhng HS ni tri.

- S dng nhiu dng kim tra v cc ch s nh gi khc nhau.

- Bo m cho tt c cc HS c c iu kin th sc u vo mt cch cng

bng v khng thin v.

- Pht trin cc hnh thc nh gi nhm cho php cc t l khc nhau ca

tin cy v hng th.

- Tm kim nhng HS c du hiu tim n bng nhng cch thc a dng, k

c nhng cch khng rnh mch.

- Ch nhng nhn t ng c nh nim hng th, s n lc v cm xc

trong vic nh gi ti nng

1.1.2. Bi dng hc sinh gii bc Trung hc Ph thng ca Vit Nam

- V thi gian, mn thi, kt qu cc nm gn y: k thi HSG quc gia THPT

hng nm thng din ra vo thng 1 hoc thng 2. Cc th sinh d thi 11 hoc 12

mn thi gm Ng vn, Ton hc, Vt l, Ha hc, Sinh hc, Lch s, a l, Tin hc

v cc mn ngoi ng.

- V khu t chc thi v thi: t nm 2007, khu t chc k thi HSG quc

gia c ba vn ln c thay i:

+ Th nht, t chc thi HSG theo 9 cm, ti cc trng i hc trn a bn

Thi Nguyn, Sn La, H Ni, Vinh, Nng, Lt, Tp.H Ch Minh, Cn Th.

B Gio dc v o to ra quyt nh thnh lp cc hi ng coi thi v iu ng

gim th t ni khc n.

+ Th hai, s khng phn bng A, B nh trc. Thay vo s ch c mt

cho cc i tuyn thi cng mt mn, sao cho nhng HS thc gii ca bng B trc

y c bn lm c bi. Thm vo , c ch thng im: th sinh thuc cc

vng (theo cch phn vng trong k thi tuyn sinh vo i hc, cao ng) c cng

7

im u tin khi xt gii; th sinh thuc vng I c cng 1,5 im cho mi bi thi;

th sinh thuc vng II v vng II nng thn c cng 1,0 im cho mi bi thi

(thang im 20).

+ Th ba, i vi cc mn thi Ton hc, Vt l, Ha hc, Sinh hc v Tin hc

s ch t chc mt bui thi nh cc mn thi khc (trc y c hai bui thi).

+ Cc n v c i tuyn d thi phi t thnh lp v bi dng, khng lin

h, mi ngi ngoi n v d thi n luyn, tp hun cho ngi dy, ngi hc di

bt k hnh thc v thi gian no.

+ Cng t nm 2007, thi HSG quc gia c ci tin theo hng: thay i

mnh cu trc thi t lun (tng s cu hi ring bit sao cho mi cu ring bit

khng qu 3 im trong tng s 20 im ca bi thi, ring Vn hc c th c 1

cu 5/20 im), khuyn khch ra cu hi trc nghim trong thi, chng hn, i

vi mn Sinh hc, Vt l c phn trc nghim nh trong cc thi Olympic quc t;

hng ci tin th hai l c phng n lp ngn hng cu hi thi cho cc k thi

HSG, phc v vic rt thm ngu nhin xy dng thi.

+ thi thng c t 5 n 7 cu. Thi gian lm bi mt mn theo hnh thc

t lun l 180 pht; theo hnh thc trc nghim l 90 pht; cn i vi mn va kt

hp c t lun v trc nghim th 90 pht t lun v 45 pht trc nghim. Thang

dnh cho mi mn l 20 im.

Trc khi k thi HSG quc gia din ra th cc trng THPT khng chuyn bi

dng, t chc thi chn ra HSG thi tnh. Tu thuc vo tng tnh m thi gian v

hnh thc thi khc nhau ph hp vi yu cu thi i hc v thi HSG quc gia.

1.1.3. Tng quan vn nghin cu

Vic nghin cu cc vn bi dng cho HS nng lc t duy, sng to, nng

lc gii quyt vn t trc n nay c nhiu cng trnh nghin cu ca cc tc

gi nh GS.TS Nguyn Ngc Quang nghin cu l lun v bi ton ha hc;

PGS.TS Nguyn Xun Trng, PGS.TS L Xun Trng, PGS.TS Nguyn Hu

nh, PGS.TS Trn Thnh Hu nghin cu v BTHH nng cao; TS V Anh Tun

nghin cu phn ha hc THPT ni chung bao gm cc phn ha hc i cng,

ha hc v c, ha hc hu c m cha i su nghin cu tng chuyn cng nh

cha a ra cc phng php s dng HTLT v BTHH tng phn mt cch hp l,

8

hiu qu khi bi dng HSGHH. Vn bi dng HSGHH phn hu c n nay

cha c lun vn hay lun n no i su nghin cu v HTLT, BTHH nng cao

cht lng, hiu qu bi dng HSGHH cc trng THPT khng chuyn.

1.2. Hc sinh gii ha hc

1.2.1. Khi nim hc sinh gii ha hc

T khi nim v HSG ta c th hiu HSGHH l nhng HS c nng lc ni

tri, c biu hin v kh nng hon thnh xut sc cc hot ng v cc lnh vc tr

tu, s sng to, c bit l c kh nng chuyn bit trong hc tp v nghin cu

ha hc. Nh vy HSGHH c kin thc ha hc c bn, vng vng, su sc v h

thng, bit vn dng linh hot v sng to kin thc ha hc vo tnh hung mi, c

nng lc t duy khi qut v sng to. ng thi cn c k nng thc nghim thnh

tho v c nng lc nghin cu khoa hc ha hc.

1.2.2. Nhng phm cht v nng lc quan trng nht ca mt hc sinh gii ha

hc cn bi dng v pht trin [35]

1.2.2.1. Nng lc tip thu kin thc

- Kh nng nhn thc vn nhanh, r rng v nhanh chng vn dng vo tnh

hung tng t (tch hp kin thc).

- Lun ho hng trong cc tit hc, nht l bi hc mi.

- C thc t b sung, hon thin nhng tri thc thu c.

1.2.2.2. Nng lc suy lun logic

- Bit phn tch cc s vt, hin tng qua cc du hiu c trng ca chng.

- Bit thay i gc nhn khi xem xt mt s vt, hin tng.

- Bit cch tm con ng ngn sm i n kt lun cn thit.

- Bit xt cc iu kin cn thit t c kt lun mong mun.

- Bit xy dng cc phn v d loi b mt s min tm kim v ch.

- Bit quay li im va xut pht tm ng i mi.

1.2.2.3. Nng lc c bit

- Bit din t chnh xc iu mnh mun.

- S dng thnh tho h thng k hiu, cc qui c din t vn .

- Bit phn bit thnh tho cc k nng c, vit v ni.

- Bit thu gn v trt t ha cc vn dng khi nim trc m t cho cc

khi nim sau.

9

1.2.2.4. Nng lc lao ng sng to

Bit tng hp cc yu t, cc thao tc thit k mt dy hot ng, nhm t

n kt qu mong mun.

1.2.2.5. Nng lc kim chng

- Bit suy xt ng, sai t mt lot s kin.

- Bit to ra cc tng t hay tng phn khng nh hoc bc b mt c

trng no trong sn phm do mnh lm ra.

- Bit ch ra mt cch chc chn cc d liu cn phi kim nghim sau khi

thc hin mt s ln kim nghim.

1.2.2.6. Nng lc thc hnh

- Bit thc hin dt khot mt s thao tc th nghim.

- Bit kin nhn v kin tr trong qu trnh lm sng t mt s vn l thuyt

qua thc nghim hoc i n mt s vn l thuyt mi da vo thc nghim.

Ha hc l b mn khoa hc thc nghim nn i hi HS phi c nng lc thc

nghim, tin hnh cc th nghim ha hc.

1.2.2.7. Nng lc vn dng kin thc gii quyt cc vn thc tin

HS c nng lc vn dng cc kin thc hc gii quyt cc vn lin

quan n thc t, sn xut hng ngy.

1.2.3. Nhng k nng cn thit ca gio vin bi dng hc sinh gii ha hc

1.2.3.1. Cc nhm k nng c bn

- Nhm k nng nhn thc

+ c, hiu, khi qut, tng hp v tm tt ti liu.

+ Xy dng cng, bin son gio n, lp k hoch bi dng.

- Nhm k nng truyn t

+ K nng giao tip, ngn ng.

+ K nng chuyn i, pht trin kin thc.

+ K nng nu vn v t cu hi.

- Nhm k nng t chc v qun l

+ Gim st, theo di, ng vin, khuyn khch.

+ Tip nhn, iu chnh thng tin phn hi.

- Nhm k nng s dng cc phng tin dy hc

10

+ Thc hnh (thao tc, quan st, gii thch, kt lun).

+ Cc thit b h tr (tranh, nh, phng tin nghe nhn, ).

- Nhm k nng kim tra, nh gi

+ Xy dng ngn hng cu hi, kim tra t cc cu hi tng ng.

+ Phn loi kim tra theo i tng, thi lng, chng trnh tp hun.

1.2.3.2. Mt s chi tit trong k nng

- K nng t cu hi

+ Cu hi c din t r rng, ngn gn, xc tch, d hiu, s dng t ng

ph hp, khng qu phc tp.

+ Cu hi c th t logic, hnh thc thay i v khng mang tnh p buc.

- K nng trnh by

+ Nm vng vn cn trnh by, chun b chu o, cn tp trnh by trc.

+ Ni r rng v m lng, bao qut tt v ch thi phn hi t HS.

- K nng cung cp thng tin

+ Nu r mc ch hoc trng tm ca bi hc.

+ S dng cc phng tin dy hc ph hp.

+ S dng ngn ng thch hp v din t cc theo th t logic.

+ Nhn mnh cc chnh v lin tc lin kt cc vi nhau.

+ Kt thc r rng v c nhc li trng tm ca bi hc.

1.2.4. Thc trng ca cng tc bi dng hc sinh gii ha hc trng Trung

hc ph thng hin nay

- Ni dung chng trnh ha hc THPT cp nhng kin thc c bn,

nhng cn thiu nhiu so vi cc l thuyt ch o. Nhiu vn cn phi bt HS

v GV chp nhn, gii thch nm na khng bn cht. Nhiu cu hi v bi tp mang

tnh cht gi nh, thiu thc t.

- GV khng xc nh c gii hn ca cc kin thc cn ging dy cho HS

sao cho hp l v i lc thi cp kin thc qu rng.

- Chng trnh ha hc THPT mang tnh cht nh lng trn c s nh tnh.

- Thi gian thc hin bi dng HSG ca cc trng cn nhiu hn ch.

- Trang thit b, cc loi my mc cn thiu, nht l i vi b mn ha hc.

11

Trc tnh hnh cc thi HSG cp tnh bt buc phi cp n nhng

ni dung c nhng c im trn v vic tuyn chn kh c th chnh xc c,

ng thi c tuyn chn HS phi mt mt thi gian rn luyn theo hng trn

v sau cng c nhng HS khng iu chnh c quan im t duy ca mnh

dn n tnh trng mt nhiu thi gian hc m hiu qu khng cao.

1.2.5. Pht hin hc sinh c th tr thnh hc sinh gii ha hc

- Lm r mc nm vng mt cch y chnh xc kin thc, k nng, k

xo theo chun kin thc k nng ca chng trnh v sch gio khoa. Mun vy

phi kim tra HS nhiu phn ca chng trnh, kim tra c kin thc l thuyt, bi

tp v thc hnh. Linh hot thay i mt vi phn trong chng trnh, nhm mc

ch o kh nng tip thu ca mi HS trong lp v vic ging dy l thuyt l mt

qu trnh trang b cho HS vn kin thc ti thiu trn c s mi pht hin c

nng lc sn c ca mt vi HS thng qua cc cu hi cng c, nghin cu, cc li

pht biu v cc bi luyn tp.

- Lm r trnh nhn thc v mc t duy ca tng HS bng nhiu bin

php v nhiu tnh hung. GV cn to ra cc tnh hung c vn o mc t

duy ca tng HS. c bit l nh gi kh nng vn dng kin thc mt cch

linh hot, sng to.

- Cn ch n logic chng trnh v pht hin nng lc ca HS cn

cp cc hc thuyt, nh lut c bn su sc ngay t u. Khi dy v ha hc hu c

th nn theo trnh t t cu hnh n cc loi ng phn (ng phn cu to, ng

phn hnh hc) n cc loi hiu ng trong ha hc hu c. Ging dy cc bi v

anehit, ancol, axit cacboxylic, cn kt hp cc kin thc v nhim v bo v

mi trng, v tc hi ca cc cht trn n sc khe v i sng con ngi.

12

TIU KT CHNG 1

Trong chng ny chng ti trnh by:

- Tng quan v vn bi dng HSG Vit Nam gm cc phn: quan nim

ca th gii v gio dc HSG; khi nim HSG; mc tiu dy HSG; phng php v

cc hnh thc gio dc, nh gi HSG; tng quan v vn nghin cu.

- Gii thiu khi qut v cng tc t chc thi, thi gian thi trong cc k thi

HSG quc gia thi gian gn y. Gii thiu v i tng tham gia, s lng th sinh

d; mt s u tin dnh cho HSG quc gia, nhng thay i trong k thi HSG quc

gia t nm 2007 n nay.

- Nu c cc vn lin quan n HSGHH nh: khi nim HSGHH; nhng

phm cht v nng lc quan trng nht ca mt HSGHH cn bi dng v pht

trin; nhng k nng cn thit ca GV khi bi dng HSGHH; thc trng ca cng

tc bi dng HSGHH trng THPT hin nay; ni dung v mt s bin php pht

hin HS c th tr thnh HSGHH.

13

CHNG 2

H THNG L THUYT V BI TP HA HC HU C S DNG

TRONG VIC BI DNG HC SINH GII

2.1. Cc chuyn ha hc hu c

- Trn c s phn tch, tm hiu cc ni dung quan trng, ph bin, thng

cp trong cc thi HSGHH chng ti quyt nh la chn v a ra mt s

chuyn trng tm v ha hc hu c.

- xy dng cc chuyn ca hp cht hu c chng ti da trn cc ti

liu ca cc tc gi Trn Quc Sn, Nguyn nh Triu, nh Rng, Thi Don

Tnh, Ng Th Thun, L Huy Bc, ng nh Bch, Nguyn Vn Tng, Nguyn

Trng Th, Qua ti liu ca cc tc gi trn chng ti tm hiu, phn tch, kt

hp vi kinh nghim ging dy ca bn thn, chng ti a ra HTLT v BTHH

ph hp vi ni dung v chng trnh bi dng HSGHH THPT. Cc chuyn

c xy dng mt cch c ng, ngn gn. Mi chuyn ch cp n cc ni

dung trng tm, thng gp trong cc thi HSG tnh, quc gia. V BTHH ch a

ra cc bi tp trng tm, c trng cho mi chuyn , cc bi tp c tnh cht vn

dng, tng hp c a ring trong a CD km theo.

- V s lng chuyn , chng ti xy dng c 6 chuyn c tnh cht

tng qut ton b chng trnh hp cht hu c. Cu trc chung ca mi chuyn

u gm 2 phn:

+ H thng l thuyt c bn: trong phn ny chng ti trnh by nhng nt c

trng, nhng kin thc quan trng m HS cn nm vng vn dng gii quyt cc

vn lin quan. Thng qua HTLT hc sinh c th t c trc nh hoc cc em

s trao i, tho lun vi nhau nhng vn kh, trng tm; GV s tng kt, nhn

xt. Qua , GV c nhiu thi gian hn tp trung cho cc em lm bi tp vn

dng.

+ Bi tp vn dng: c l y l im ni bt nht ca mi chuyn . i

tng dy hc l HS tham d cc k thi HSG tnh, quc gia nn i vi cc em cn

phi c h thng BTHH tht a dng, phong ph, ni dung chun xc, c kh

nht nh cc em rn luyn. Chnh v vy h thng BTHH c t ln hng u.

Trong mi chuyn chng ti xy dng bi tp (trc nghim t lun v trc

nghim khch quan) vi y cc dng, t n gin n phc tp. Hng dn gii

hoc gi ca nhng bi tp kh c a vo ph lc ca lun vn.

14

2.1.1. Chuyn 1. i cng ho hc hu c

(Thi lng: 6 tit)

2.1.1.1. H thng l thuyt c bn

LIN KT TRONG HO HC HU C

- Lin kt ho hc thng gp nht trong phn t cc hp cht hu c l lin

kt cng ho tr. Lin kt cng ho tr c chia lm hai loi: lin kt xich ma ()

v lin kt pi ( ).

+ Lin kt c tnh i xng trc, c xen ph cc i nn c nng lng ln,

c mt phng i xng i qua nhn v mt i xng thng gc vi trc lin kt, c

kh nng quay xung quanh trc m lin kt vn bo ton. Thng gp cc lin kt

: C-H, C-C, C-O, C-N, C-Cl, C-P,

+ Lin kt c xen ph yu hn nn nng lng lin kt thp hn, c mt

phng i xng thng gc vi trc i qua nhn, c mt phng bt i xng i qua

trc lin kt, km hm s quay xung quanh trc lin kt. Thng gp cc lin kt:

C=C, C=O, C=N,

- Lin kt n (hay lin kt ) do mt cp electron chung to nn v c biu

din bng mt gch ni gia hai nguyn t. Lin kt l lin kt bn.

- Lin kt i do 2 cp electron chung gia hai nguyn t to nn. Lin kt i

gm mt lin kt v mt lin kt , c biu din bng hai gch ni song song

gia hai nguyn t. Lin kt km bn hn lin kt nn d b t ra trong cc

phn ng ho hc.

- Lin kt ba do 3 cp electron chung gia hai nguyn t to nn. Lin kt ba

gm mt lin kt v hai lin kt , c biu din bng ba gch ni song song

gia hai nguyn t.

NG PHN TRONG HP CHT HU C

a) ng phn cu to

- Khi nim, phn loi: ng phn cu to cn gi l P phng, y l loi P

n gin v c trnh by kh r rng trong cc loi sch gio khoa. ng phn

cu to bao gm P mch cacbon; P v tr nhm chc; P nhm chc.

- Cch tnh bt bo ha (tng s lin kt v s vng)

15

+ bt bo ha chnh l tng s lin kt v s vng trong hp cht hu

c, k hiu l k. Cng thc chung tnh k:

k = (2a + 2 + b c)/2

a, b, c ln lt l s nguyn t ha tr IV, III, I.

+ Vi hp cht hu c c cng thc CxHyOzNtClu, biu thc tnh k nh sau:

k = (2x + 2 + t y u)/2

+ Nu N c cha lin kt cho nhn (v d mui amoni) th biu thc tnh k:

k = (2x + 2 + 3t y u)/2

b) ng phn hnh hc

- Khi nim: ng phn hnh hc (hay P cis/trans) l loi P khng gian do

s phn b khc nhau ca cc nguyn t hoc nhm nguyn t hai bn b phn

cng nhc nh ni i, vng no,

- iu kin xut hin ng phn hnh hc

+ iu kin cn: phn t phi c lin kt i (mt lin kt i hoc h thng

mt s lin kt i) hoc vng no (thng l vng nh, s cnh 4).

+ iu kin : mi nguyn t cacbon ca lin kt i v t nht hai nguyn t

cacbon ca vng no phi c 2 nguyn t hoc nhm nguyn t khc nhau.

- Cc trng hp xut hin ng phn hnh hc

+ Trng hp c mt lin kt i: abC = Cef (a b; e f).

+ Trng hp c nhiu lin kt i: abC=C=C=Cef, h ny c vai tr tng t

mt lin kt C=C.

CC LOI HIU NG TRONG HP CHT HU C

a) Hiu ng cm ng

- Bn cht: s phn cc cc lin kt do s khc nhau v m in. S phn

cc lan truyn theo mch lin kt c biu th bng du mi tn thng. V d:

CH3CH2CH2Cl, lin kt CH2Cl phn cc v Cl, do cc lin kt CH3

CH2; CH2CH2 t nhiu cng b phn cc. Hiu ng cm ng c k hiu l I.

- Phn loi: Gm 2 loi: H tnh (ni phn t), H ng (do mi trng tc

ng). Sau y ch cp H tnh, khng xt H ng. H tnh gm 2 loi: hiu

ng cm ng dng (+I) v hiu ng cm ng m (I).

- c im: hiu ng cm ng gim nhanh khi mch lin kt ko di.

16

- Quy lut

+ H +I: cc nhm ankyl gy H +I; H ny cng tng khi mch C cng

tng v cng phn nhnh. V d: -CH3 < -C2H5 < -CH(CH3)2 < - C(CH3)3. Cc

nhm mang in tch m th cng thng xuyn gy H +I.

+ H I: tng khi m in cng ln. V d NH2 < OH < F.

H I tng theo v tr lai ha ca cacbon, c th 3 2 spsp spC C C .

b) Hiu ng lin hp

- Bn cht: hiu ng lin hp l s dch chuyn v phn b li mt trn

h lin hp do s khc nhau m in. hiu ng lin hp k hiu l C, biu th

bng du mi tn cong.

C C C Z

- Phn loi: gm hai loi hiu ng lin hp dng (+C) v hiu ng lin hp

m (C)

+ Mt s nhm c H +C: O(), S(), N(); OH, OR, SH, SR; NH2,

NR2; F, Cl, Br; NHCOCH3,

+ Mt s nhm c H C: NO2, CHO, COOH; C N, COR; CONH2,

NHCOCH3,

- c im ca hiu ng lin hp: hiu ng lin hp hu nh khng i (hoc

gim rt t) khi h lin hp ko di. hiu ng lin hp chu s nh hng ca khng

gian. V d:

OH

OH

NO2

OH

CH3

CH3

NO2

.. ..

-C, -I -C, -I

pK = 9,98 pK = 7,16 pK = 8,24a a a

- Quy lut

+ H +C: cc nguyn t, nhm nguyn t c cp electron cha chia (en)

thng gy H +C. Trong cng chu k, H +C cng mnh khi m in cng

17

nh. V d: H +C theo th t NR2 > OR > F. Trong cng phn nhm chnh,

H +C ph thuc vo bn knh nhiu hn ph thuc vo m in. Xt v d vi

F, Cl, Br, I, ta thy m in tng theo chiu: I, Br, Cl, F; bn knh tng theo

chiu: F, Cl, Br, I, H +C ph thuc vo bn knh nn theo chiu bn knh tng th

H +C gim.

+ H C: H C ph thuc vo m in ca nhm Z. Nu Z c m

in cng ln th H C cng ln. V d:

C CH2 C NH C O

( )1 ( )2 ( )3

m in tng theo th t C, N, O nn cng thc ca cht (3) c H C ln

nht, cng thc ca cht (1) c H C nh nht. Hai hay nhiu nhm tng t

nhau, nhm no c in tch dng ln hn s c H C ln hn. H C ph

thuc vo bn cht ca nhm lin kt vi n.

OHNO

O

C -C-C+ C+

c) Hiu ng siu lin hp

- Bn cht: hiu ng lin hp l hiu ng lin hp c bit gia cc e ca lin

kt CH hoc CC (ca vng 3, 4 cnh) vi cc e (ni i hoc vng benzen).

- Mt s trng hp c hiu ng siu lin hp

HH

HCH CH2 CH

H

HC CH3

CH3

+C

H

H

H

C N..

( )1 ( )2 ( )3 ( )4

(1) Hiu ng +H gia 3 nhm CH vi vng benzen

(2) Hiu ng +H gia vng 3 vi e

(3) Hiu ng +H gia 3 nhm CH vi +

(4) Hiu ng +H gia 3 nhm CH vi e

- Th t hiu ng siu lin hp

+ Gc ankyl, ngoi hiu ng cm ng cn c hiu ng siu lin hp dng +H

+ H +H cng mnh khi s lin kt CH cng nhiu

18

2.1.1.2. Bi tp vn dng

A. TRC NGHIM T LUN

Bi 1.

a) Nhng hp cht no cho di y c ng phn hnh hc. Vit cng thc

cu to v gi tn chng theo danh php cis, trans.

1. CHCl=CHBr

2. CH2=CH-CH3

3. CH3-CH=CH-CH3

4. C2H5(CH3)C=C(C2H5)CH2CH2CH3

5. (C2H5)2C=CH-CH3

6. CHCl=CHCl

7. CH3-CH=CH-CH=CH-CH3

8. C6H5-CH=CH-CH=CH-COOH

b) Biu din ng phn hnh hc ca cht: CH3-CH=CH-CH=CH-CH=CH2

Bi 2.

a) So snh tnh baz ca cc cht: CH3NH2; CH3NHCH3; (CH3)3N

b) So snh tnh baz ca cc cht:

NH3NH2 CH3 NH2

c) So snh tnh axit ca cc cht:

OH CH3 CH2 COOH

(3)(2)

CH3 CH2 OH

(1)

Bi 3.

a) Da vo cc loi hiu ng ha hc, hy cho bit s nh hng trong cc

phn ng th ca phenol vi tc nhn th.

b) Gii thch s nh hng tc nhn th vo nhn benzen khi cho toluen tc

dng vi HNO3, xc tc anhirit axetic.

c) Khi cho nitro benzen tc dng vi HNO3 c H2SO4 c lm xc tc, un

nng. Hy cho bit c nhng sn phm no to thnh? Sn phm no l sn phm

chnh?

Bi 4. Da vo bn cht ca lin kt hiro gia cc phn t, hy cho bit v

gii thch:

a) Cht no c nhit si cao nht: CH3COOH; CH3COCH3; C6H5OH

b) Cht no d ho lng nht: CH4; F2; C2H2; NH3

c) Cht no d tan trong nc nht: C2H2; C2H5Cl; C6H6; NH3

19

d) o-nitrophenol c t0s v tan thp hn ng phn meta v para ca n

e) Trong hn hp etanol v phenol c my loi lin kt hiro? Loi no bn

nht?

g) V sao khi cho etanol vo nc th th tch dung dch thu c li gim so

vi tng th tch hai cht ban u?

Bi 5.

a) Licopen (cht mu trong qu c chua) C40H56 ch cha lin kt i v

lin kt n trong phn t. Khi hiro ho hon ton licopen cho hirocacbon no

C40H82. Tnh s ni i trong phn t licopen.

b) Caroten (cht mu vng trong c c rt) l ng phn ca licopen. Khi

hiro ho hon ton caroten cho hirocacbon no C40H78. Tnh s ni i trong phn

t caroten.

B. TRC NGHIM KHCH QUAN

Cu 1. Cho cc hp cht sau:

CH = CH2 CH2 - CH3 CH3 - CH - CH3 CH3

CH3

CH3

(I) (II) (III) (IV) (V)

Cc hp cht no l ng ng ca benzen l:

A. I, II, III B. II, III, V C. I, IV, V D. II, III, IV

Cu 2. Cho cc cht C4H10O, C4H9Cl, C4H10, C4H11N. S ng phn cu to ca cc

cht gim theo th t l:

A. C4H11N, C4H10O, C4H9Cl, C4H10 B. C4H10O, C4H9Cl, C4H11N, C4H10

C. C4H10O, C4H9Cl, C4H10, C4H11N D. C4H10O, C4H11N, C4H10, C4H9Cl

Cu 3. Cho cc hp cht sau:

OH

Br

(I) (II) (III)

Cht c ng phn hnh hc l:

A. (III) B. (II) C. (I) D. (I), (II) v (III)

20

Cu 4. Cho cc cht sau: Phenol (1); p-metyl phenol (2); ancol benzylic (3); p-

nitro phenol (4); axit benzoic (5); anehit benzoic (6). Chiu tng dn tnh axit ca

cc cht l:

A. (4)

21

Cu 10. Caroten, cht mu da cam trong c c rt (C40H56) cha lin kt i v

vng trong phn t. Khi hiro ha hon ton caroten thu c hirocacbon no

C40H78. S ni i v s vng trong phn t caroten tng ng l:

A. 2 v 11 B. 11 v 2 C. 10 v 3 D. 3 v 10

Cu 11. t chy hon ton 1 lt hn hp kh gm C2H2 v hirocacbon X sinh ra 2

lt kh CO2 v 2 lt hi H2O (cc th tch kh v hi nc cng iu kin nhit ,

p sut). Cng thc phn t ca X l:

A. C2H6 B. C2H4 C. CH4 D. C3H8

Cu 12. Mt hp cht hu c X mch h cha (C,H,O) c khi lng phn t l

60(u). X tc dng vi Na gii phng H2. S cc cht tho mn gi thit trn l:

A. 5 B. 2 C. 3 D. 4

Cu 13. Mt hp cht hu c X mch h cha (C,H,O) c khi lng phn t l

88(u). X tc dng vi NaOH to mui ca axit hu c. S cc cht tho mn gi

thit trn l:

A. 5 B. 4 C. 3 D. 6

Cu 14. t chy hon ton hp cht hu c X (phn t c cha C,H,O) cn 0,4

mol O2 thu c 0,35 mol CO2 v 3,6 gam H2O. Bit MX < 200 vc. Cng thc

phn t ca X l:

A. C7H8O B. C7H8O2 C. C7H8O3 D. C3H4O2

Cu 15. Nicotin l mt cht c c trong khi thuc l, khi phn tch thnh phn

ca nicotin thu c kt qu sau: C chim 74,074%, H chim 8,642% cn li l

nit. Bit trong phn t nicotin c 2 nguyn t nit. CTPT ca nicotin l:

A. C10H14N2 B. C10H15N2 C. C12H16N2 D. C12H14N2

BI TP TNG HP (Xem CD)

2.1.2. Chuyn 2. Hirocacbon

(Thi lng: 12 tit)

2.1.2.1. H thng l thuyt c bn

HIROCACBON NO

Hirocacbon no l hirocacbon ch cha lin kt trong phn t, gm 2 loi l

ankan (mch h) v xicloankan (mch vng).

22

ANKAN

Ankan (hay parafin) l hirocacbon no, mch h, c cng thc chung CnH2n+2

(n 1). Ankan sau khi mt 1 nguyn t H s to thnh gc hirocacbon (gc ankyl).

a) ng phn

T C4H10 tr ln mi c P mch cacbon. S nguyn t cacbon (n) trong ankan

(CnH2n+2) cng ln th s ng phn cu to (t) cng tng mnh. V d:

n 3 4 5 6 7 8 9 10 15 20

t 1 2 3 5 9 18 35 75 4347 366319

b) Danh php

Tn ankan: s ch v tr nhnh + tn nhnh + tn cacbon mch chnh + an.

+ Mch chnh: mch di nht, nhiu nhnh nht.

+ nh s cacbon mch chnh: xut pht t u gn mch nhnh cho ch s

v v tr nhnh l nh nht. Nu c nhiu nhnh m cch nh khc nhau dn ti hai

b ch s khc nhau th chn b no c ch s nh hn trong ln gp u tin (cho

d tng ch s c ln hn). V d:

CH3 C

CH3

CH3

CH2 CH CH2 CH3

HC CH3

CH3

1 2 3 4

5

6

4-Etyl-2,2,5-trimetylhexan

c) Tnh cht vt l

Phn t ankan hu nh khng phn cc ( = 0). iu kin thng, t C1 n

C4 (kh), C5 n C19 (lng), t C20 tr ln (rn). Mch ankan b phn nhnh, t0s ca

ankan gim i. Cc ankan u nh hn nc, khi lng ring tng theo mch

cacbon, song gii hn ti a bng 0,8 g/ml.

d) Tnh cht ha hc

* P th

+ Th clo, brom: Xt CH4 + Cl2: P xy ra theo c ch gc, gm ba bc.

Bc 1. Bc khi mo P: Cl2 hp th nng lng nh sng b phn ct

thnh hai nguyn t clo.

ClCl 2Cl H = 243 kJ/mol as .

23

Bc 2. Bc pht trin mch dy chuyn ca P: nguyn t clo hot ng

mnh ly i nguyn t H ca CH4 to HCl v gc t do

CH3H + Cl HCl + CH3 H = 4 kJ/mol

CH3 + ClCl CH3Cl + Cl H = 97 kJ/mol ..

. .

Bc 3. Bc tt mch P: cc nguyn t v gc t do kt hp vi nhau to

thnh cc phn t bn vng.

Cl + Cl Cl2 H = 243 kJ/mol Cl + CH3 CH3Cl H = 351 kJ/mol CH3 + CH3 CH3CH3 H = 370 kJ/mol

. .

. .. .

Nu c nhiu sn phm monohalogen th t l % cc sn phm ph thuc vo

s lng nguyn t H cng loi v kh nng phn ng ca nhng nguyn t hiro

. Kh nng phn ng tng theo trnh t ICH < IICH < IIICH v bc cacbon cng

cao, gc t do trung gian sinh ra cng bn v cng lm tng tc phn ng.

+ Nitro ha v sunfoclo ha: to ra hp cht nitro v clorua ca axit

ankansunfonic.

RH + HNO3 RNO2 + H2O

RH + SO2 + Cl2 RSO2Cl + HCl

* P tch

+ Tch H2: thng xy ra vi ankan mch ngn v cn xc tc Cr2O3, Cu,

Pt, to hirocacbon khng no. Ring trng hp CH4 khng th c P tch bnh

thng m ty iu kin c th thu c axetilen hoc mui than vi hiro.

+ P crackinh: b gy mch cacbon ca ankan to ra hn hp cc ankan v

anken c mch cacbon ngn hn. P crackinh gm crackinh nhit v crackinh xc

tc.

e) iu ch ankan

- Nung khan mui natri ca axit cacboxylic vi NaOH ( dng vi ti xt):

Thng dng iu ch ankan thp.

CH3COONa + NaOH CH4 + Na2CO3 CaO

t0

- Ring metan c th iu ch bng cch thy phn Al4C3.

Al4C3 + 12H2O 4Al(OH)3 + 3CH4

24

XICLOANKAN

Xicloankan l hirocacbon no, c mt hay nhiu vng.

a) ng phn

Xicloankan n vng c cc loi P v ln ca vng, v tr nhm th trong

vng, P mch nhnh.

b) Danh php

Xicloankan n vng: ly t tn ankan tng ng ch thm tin t xiclo. Nu

vng c nhnh th gi tn nhnh trc. Nu nhiu nhnh, cn nh s sao cho tng

s cc ch s nh nht. V d:

CH3

CH3CH3

CH3

C2H5

1 2

3

4

5

12

3

4

5

6

1,2,4-trimetylxiclopentan 1-etyl-4-trimetylxiclohexan

Tn cc gc ha tr mt c ly t tn xicloankan tng ng ch i ui

an thnh yl.

c) Tnh cht ha hc ca xicloankan n vng

* P cng m vng: ch c xiclopropan v xiclobutan c P cng m vng,

cc P tng t hirocacbon khng no. Vng 5, 6 cnh tr ln khng tham gia P

cng m vng. Vng 4 cnh ch P cng m vng vi tc nhn l H2, vng 3 cnh

c th cng m vng vi tc nhn H2, Br2, HBr, H2SO4,

* P th: vng bn tham gia P th nh ankan.

HIROCACBON KHNG NO

Hirocacbon khng no l hirocacbon c cha lin kt i hoc lin kt ba

hoc c hai loi lin kt trong phn t.

ANKEN

Anken (hay olefin) l hirocacbon khng no, c mt lin kt i C=C, mch

h, cng thc chung CnH2n (n 2).

a) ng phn: anken c 2 loi P: ng phn cu to v ng phn hnh hc.

+ ng phn cu to: so vi ankan, anken cn c thm P lin kt i.

+ ng phn hnh hc: cc hirocacbon c cc nhm nguyn t khc nhau gn

vo cc bon ni i C=C s c ng phn hnh hc.

25

b) Danh php

+ Danh php thng: gi tng t ankan nhng i hu t an thnh ilen.

+ Danh php IUPAC: gi tng ankan, thay hu t an thnh en v c

thm s ch v tr lin kt i (t buten tr ln). nh s t pha gn lin kt i

hn. Nu c ng phn hnh hc th ghi cis hoc trans trc tn gi. Tn gc

hirocacbon c hu t enyl, mch nhnh c nh s t nguyn t cacbon mang

ha tr t do.

V d CH2=CH: etenyl hay vinyl; CH3CH=CH: prop1enyl; CH2=CH

CH2: Prop2enyl hay anlyl; CH2=CHCH(CH3): 1metylprop2enyl.

c) Cu trc phn t

- Cu to lin kt i C=C

C Csp2 sp2

- So vi lin kt n CC th lin kt i C=C c di lin kt ngn hn;

nng lng lin kt i C=C nh hn nhiu. iu chng t rng lin kt linh

ng hn v d b t ra trong cc PHH.

d) Tnh cht vt l

So vi ankan th ank1en c t0s v t0nc thp hn, t khi ln hn. Cc trans

anken c t0nc cao hn nhng t0s li thp hn so vi cc P cis tng ng.

e) Tnh cht ha hc

Trung tm P ca anken l ni i, lin kt d t ra v d dng tc dng

vi tc nhn nucleophin. P c trng nht ca anken l P cng vo ni i. P

trng hp v bn cht cng l mt dng ca P cng. P oxi ha ni i xy ra

kh d dng v c ngha quan trng.

* P cng (H2, Br2, Cl2, hiro halogenua)

+ Cng brom v clo: P d xy ra trong cc dung mi CCl4, CHCl3, H2O,

CH2=CH2 + Br2 BrCH2-CH2Br + BrCH2-CHCl (54%) (46%)

CH2=CH2 + Br2 BrCH2-CH2Br + BrCH2-CHOH (37%) (63%)

NaCl bo ho

+ Cng hiro halogenua: nu c nhiu sn phm, sn phm chnh tun theo

quy tc Maccopnhicop. Khi cng hiro halogenua vo anken, HI tc dng d dng

26

nht, cn HF kh khn nht: HI > HBr > HCl >> HF. V vy ngay c HCl 37%

cng khng cng vo etilen, ch khi dng HCl khan c cht xc tc (AlCl3, ) P

cng mi xy ra. Cc P cng H2SO4, H2O (xc tc H+) cng xy ra theo c ch

cng electrophin nh trn v cng tun theo quy tc Maccopnhicop.

CH2=CHCH3 + HOSO3H CH3CH(OSO3H)CH3

Isopropyl hiro sunfat

* P oxi ha: oxi ha bng KMnO4 trong nc hoc kim long, ngui, oxi

ha ni i ca anken thnh 1,2iol.

3CH2=CH2 + 2MnO4-

+ 4H2O 3HOCH2CH2OH + 2MnO2 + 2OH

-

(mu hng) (mu nu en)

Da vo s bin i mu (dung dch mu hng sang kt ta nu en) P trn

dng nhn bit s c mt ca ni i, ni ba. Dung dch KMnO4 trong axit (un

nng) oxi ha mnh lm t mch cacbon ch ni i.

CH3CH2C(CH3)=CHCH3 CH3CH2C(CH3)=O + CH3COOH KMnO4/H

+

t0

P ny dng xc nh v tr ca ni i da vo cu to ca sn phm oxi ha.

ANKAIEN

Ankaien (hay ien) l hirocacbon khng no, c hai lin kt i C=C, mch

h, cng thc chung CnH2n2 (n 3).

a) ng phn v phn loi

- ng phn: tng t anken, ankaien cng c hai loi P: ng phn cu

to v ng phn hnh hc.

- Phn loi: da vo v tr gia hai ni i, c th chia ankaien thnh 3 loi:

+ Hai ni i lin nhau (gi l anlen): CH2=C=CH2, CH2=C=CHCH3

+ Hai ni i cch nhiu ni n (ien bit lp): CH2=CHCH2CH=CH2

+ Hai ni i cch mt ni n (ien lin hp): CH2=CHCH=CH2,

CH2=C(CH3)CH=CH2

Trong ba loi trn, loi quan trng hn c l ankaien lin hp.

b) Cu trc phn t buta1,3ankaien: cc lin kt , lin kt trong phn

t buta1,3ien u nm trn mt mt phng. Tuy nhin, cc obitan 2p trong phn

t buta1,3ien khng nhng xen ph nhau to thnh lin kt gia cc nguyn

t C1C2 v C3C4 m cn xen ph gia cc nguyn t C2C3. Do , xut hin

27

obitan bao trm tt c bn nguyn t cacbon ch khng phi ch bao trm hai cp

nguyn t cacbon. Hin tng xen ph obitan nh trn gi l hin tng lin hp.

c) Tnh cht ha hc

- Tng t anken, ankaien cng c P cng, P trng hp, P oxi ha.

Ngoi ra, ankaien cn c P va cng, va ng vng gi l P DielsAlder.

+ Cng H2: nu dng lng hn ch hiro v iu kin m du th sn phm

nh sau:

CH2 CH CH CH2

CH CH CH2CH3

CH CHCH3 CH3

CH2CH3 CH2 CH3Pd, -120C

C2H5OH

45%

49%

6%

thc hin P kh chn lc vo v tr 1,4 c th dng cht kh l

Na(Hg)/C2H5OH hoc Na/NH3 lng.

+ Cng halogen, hiro halogenua: t l hai sn phm cng 1,2 hoc 1,4 ph thuc

vo t0. Nu un sn phm cng 1,2 ln 400C n s chuyn thnh sn phm cng 1,4

theo mt cn bng. P trn xy ra theo c ch cng electrophin to cacbocation lin

hp nn c th cho c hai sn phm cng 1,2 hoc 1,4. t0 800C, P cng 1,2

xy ra nhanh hn, song 400C sn phm cng 1,4 li bn hn.

+ P cng ng vng DielsAlder: P DielsAlder l P cng 1,4 ca mt

lin kt bi (thng l C=C) ca hp phn gi l ienophin v mt ien lin hp

to ra hp cht vng 6 cnh. V d:

HC

HC

CH2

CH2

CH2

CH2

2000C

300 atm+

Nu trong phn t ien c nhm th y electron (CH3, CH3O, ) cn

trong phn t ienophin c nhm th ht electron (COOH, CHO, CN, ) th

P xy ra d dng hn.

d) Khi nim v tecpen

+ Tecpen l tn gi nhm hirocacbon khng no thng c cng thc chung

(C5H8)n (n 2), thng gp trong gii thc vt, nht l trong tinh du tho mc nh

du thng, s, qu, chanh, D mch h hay mch vng, tecpen u dng nh

do cc n v isopren C5H8 ni vi nhau theo kiu u ni vi ui.

28

+ ly tecpen t thc vt, phng php thng dng nht l chng ct li

cun hi nc thu tinh du, sau chng ct tinh du di p sut thp.

ANKIN

Ankin l hirocacbon khng no, c mt lin kt ba C C, mch h, cng thc

chung l CnH2n2 (n 2).

a) ng phn, danh php

+ Cc ankin khng c ng phn hnh hc.

+ Danh php thng: tn ca gc hirocacbon + axetilen

+ Danh php IUPAC: tn ankan tng ng, i an thnh in, c thm v tr

ni ba khi cn thit. Nu c hai, ba, ni ba ta dng aiin, atriin. Nu c mt c

ni i v ni ba ta dng enin.

CH CCH2CH2CH=CH2 Pent1en5in

CH CCH2CH2CH=CHCH3 Hex5en1in

+ Tn gc ha tr mt: tn ankin + yl; CH CCH2CH2: but3in1yl

b) Cu trc

+ Phn t ankin c lin kt ba do hai nguyn t spC to nn, v m in th

2 3sp sp spC C C . V vy phn t axetilen hai nguyn t C v hai nguyn t H nm

trn ng thng, lin kt spC H phn cc mnh hn lin kt 2spC H .

+ Nng lng lin kt ba nh hn nhiu so vi nng lng ca ba lin kt n.

iu chng t rng lin kt trong ankin linh ng v d t trong P ha hc.

c) Tnh cht ha hc

* P cng (H2, Br2, Cl2, hiro, H2O): nu dng xc tc l Pd, nht l khi dng

PbCO3 hoc BaSO4, P s dng li giai on to anken. Cng halogen xy ra

theo hai giai on, giai on sau xy ra kh khn hn giai on trc. Ni chung

ankin lm mt mu nc brom chm hn anken. Cc ng ng ca ankin cng

nc to xeton, ring axetilen to anehit.

* P th nguyn t hiro

Do s phn cc ca lin kt spC H cc ank1in c hiro linh ng hn

ankan v anken cho nn c th tham gia P th nguyn t H bng kim loi.

CH CH + 2AgNO3 + 2NH3 AgC CAg + 2NH4NO3

P trn dng nhn bit cc ank1in do to kt ta mu vng nht.

29

* P oxi ha: tng t anken, ankin d b oxi ha bi KMnO4 (mu tm mt

i, to kt ta mu nu en, ng thi to CO2, HOOCCOOH, ).

HIROCACBON THM

Hirocacbon thm (aren) l hirocacbon mch vng c tnh thm.

Hirocacbon thm cng c tnh khng no nhng cn c xt ring v tnh cht ca

n rt c trng, rt khc vi anken v ankin.

a) Danh php

+ ng ng benzen: thng c gi tn theo benzen: Tn gc ankyl +

benzen. Nu phi nh s trn vng benzen th theo quy tc tng cc s ch v tr l

nh nht. Nu c hai nhm th c th dng cc tin t ortho, meta, para thay cho

cc v tr 1,2; 1,3; 1,4. Mt s tn thng dng c IUPAC lu dng: toluen

(metylbenzen), xilen (imetylbenzen), cumen (isopropylbenzen), Cc gc thm

ha tr mt c gi l aryl.

CH2

Phenyl Benzyl

b) Cu trc ca benzen

- Phn t benzen l hnh 6 cnh, u, phng: su nguyn t C trong phn t

benzen trng thi lai ho sp2; mi nguyn t C s dng 3 obitan lai ho to lin

kt vi 2 nguyn t C bn cnh n v 1 nguyn t H. Su obitan p cn li ca 6

nguyn t C xen ph bn vi nhau to thnh h lin hp chung cho c vng

benzen. Nh vy m lin kt vng benzen tong i bn vng so vi lin kt

anken cng nh nhng hirocacbon khng no khc.

- Do cu trc nh vy nen benzen c tnh thm benzen: tnh thm l tnh cht

ca nhng h vng cha no tng i bn vng; h vng ny d tham gia cc P

th, kh tham gia P cng v kh b oxi ha; cc nhm th trong vng c nh

hng r rt v c trng n P th ca vng.

c) Tnh cht ha hc ca benzen v cc cht ng ng

* Phn ng th

+ Vi clo, brom (P halogen ha): benzen khng P vi nc brom nhng

P c vi brom nguyn cht khi c mt bt st (hoc FeBr3, FeCl3, AlCl3, ZnCl2,

). Trong iu kin nh trn, toluen tham gia P d dng hn v to hn hp hai

30

P ortho, para. Nu chiu sng (khng c Fe), toluen v etylbenzen li tham gia P

nhnh d dng hn metan.

+ Vi axit nitric (P nitro ha): un nh benzen vi hn hp HNO3 c v

H2SO4 c s xy ra P th to thnh nitrobenzen. Vi toluen, P th xy ra ngay

t0 phng v sinh ra hn hp 3 P v tr, trong sn phm l ortho (56%), para

nitro (41%).

+ Vi H2SO4 hoc SO3 (P sunfo ha): un nng benzen vi H2SO4 c ng

thi chng ct nc s thu c axit benzensunfonic (C6H5SO3H).

+ Vi dn xut halogen hoc ancol (P ankyl ha FrienCrap): benzen (ly

d) tc dng vi etyl clorua c mt AlCl3 khan lm xc tc thu c etylbenzen v

lng nh ietylbenzen.

C6H6 + C2H5Cl C6H5C2H5 + HCl AlCl3

Nu dng propyl clorua s thu c hn hp propylbenzen v

isopropylbenzen vi t l mol 1: 2. C th thay cc dn xut halogen bng ancol

hoc anken ankyl ha benzen.

C6H

6 + C

2H

5OH C

6H

5-C

2H

5 + H

2O

H2SO4

C6H

6 + CH

2=CH

2 C

6H

5-C

2H

5 + H

2O

H2SO4

+ Vi clorua axit v anhirit axit (P axyl ha FrienCrap): xc tc l AlCl3

khan, sinh ra sn phm l xeton thm.

* Phn ng oxi ha

+ Khc vi etilen v axetilen, benzen khng P vi dung dch KMnO4 nhng

toluen v cc ng ng khc ca benzen khi un nng vi dung dch KMnO4 (hoc

K2Cr2O7) li b oxi ha nhm ankyl sinh ra mui ca axit hu c.

t0C

6H

5CH

3 + 2KMnO

4 C

6H

5COOK + 2MnO

2 + KOH + H

2O

C6H

5COOK + H

3O+ C

6H

5COOH + K+ + H

2O

C6H

4(CH

3)

2 + KMnO

4 C

6H

4(COOK)

2 C

6H

4(COOH)

2t0

KMnO4 H3O+

31

+ Ba P ca xilen c t0s rt gn nhau nn kh phn bit, tri li ba P ca

axit benzenicacboxylic li c t0nc rt khc nhau. Do , dng P oxi ha trn c

th nhn ra tng P ca xilen. Nu nhm ankyl vng benzen di hn nhm CH3

nh CH2CH3, CH2CH2CH3, P oxi ha vn u tin xy ra v tr i vi

vng, ngha l chuyn tt c cc nhm thnh nhm COOH.

2.1.2.2. Bi tp vn dng

A. TRC NGHIM T LUN

Bi 1. Cho hn hp gm CH4, C2H4, C2H2. Bng phng php ha hc hy:

a) Hy phn bit cc cht trn khi chng cc l ring bit.

b) Tch ring cc cht trong hn hp trn.

Bi 2. t chy mt hirocacbon A vi lng va oxi. Ton b sn phm

chy c dn qua bnh CaCl2 khan d th th tch gim i hn mt na.

a) Xc nh CTCT ca A. Bit trong A cacbon chim 80% v khi lng.

b) Mt ng ng B ca A m hm lng cacbon trong phn t nh hn hm

lng cacbon trong A l 5%. Cho B tc dng vi rt t clo ngoi nh sng, trong s

cc sn phm thu c c A. Gii thch.

c) Hai xicloankan M v N u c t khi hi so vi metan bng 5,25. Khi

monoclo ha (c chiu sng) th M cho 4 hp cht, N ch cho mt hp cht duy

nht. Hy xc nh CTCT ca M v N.

Bi 3. A, B, C, D, E, F l su hirocacbon P. t chy hon ton A vi O2

d, sau khi ngng t nc v a v iu kin ban u th th tch hn hp kh cn

li gim 30% so vi hn hp ban u, tip tc cho qua dung dch KOH d th th

tch hn hp gim 4/7 s cn li.

a) Xc nh CTPT ca A.

b) Xc nh CTPT ca cc hirocacbon trn bit khi tc dng vi Br2 trong

CCl4 th A, B, C, D lm mt mu nhanh, E lm mt mu chm, cn F hu nh

khng phn ng. Cc sn phm thu c t B v C vi Br2 l nhng ng phn hnh

hc ca nhau, B c t0s cao hn C. Khi tc dng vi H2 (xc tc Ni, un nng) th A,

B, C u cho cng mt sn phm G.

32

Bi 4.

a) (Trch trong HSG C Mau 2004-2005)

A, B l 2 anken ng phn bit: A hay B 1 axit D duy nht RCOOH

Trong R ch c 1 loi nguyn t hidro; khi lng ring ca D l 5,36 g/l

(ktc). Tm cng thc cu to D, A, B bit A c nhit si cao hn B.

b) (Trch trong HSG Nam nh 2007 2008)

Hn hp kh X gm mt hirocacbon no mch h A v oxi. Sau khi t chy

hon ton A trong hn hp trn, ri lm ngng t hi nc cn li hn hp kh Y.

Xc nh cng thc phn t ca A. (Bit 1 lt kh X nng 1,488 gam; 1 lt kh Y

nng 1,696 gam, cc th tch kh o ktc).

c) Khi oxi ha mt hn hp 2 hirocacbon ng phn bng dung dch KMnO4

(mi trng axit) thu c 11,2 lt CO2 (ktc); 24,4 gam axit benzoic; 16,6 gam axit

terephtaic. Xc nh CTCT ca hai hirocacbon.

Bi 5. (Trch trong HSG lp 11, Nng 2007-2008)

X, Y, Z ln lt l ankan, ankaien lin hp v ankin, iu kin thng tn ti

th kh. t chy 2,45 lt hn hp ba cht ny cn 14,7 lt kh O2, thu c CO2

v H2O c s mol bng nhau. Cc th tch kh u o 250C v 1 atm.

a) Xc nh cng thc phn t ca X, Y v Z.

b) Y cng Br2 theo t l mol 1:1 to ba sn phm ng phn. Dng c ch

phn ng gii thch s hnh thnh cc sn phm ny.

Bi 6.

a) Mun iu ch PVC (-CH2-CHCl-)n ta c th cho Cl2 tc dng vi PE (-

CH2-CH2-)n c khng? Ti sao? Tng t mun iu ch teflon (-CF2-CF2-)n

dng lm cht chng dnh xoong cho c th cho F2 tc dng vi PE c khng?

Ti sao?

b) T metan v cc cht v c cn thit khc vit s P iu ch

1. Axetilen 2. Axit aipic 3. Cao su clopren

4. Phenol 5. Caosu Buna 6. Cao su isopren

7. Alinin 8. Caosu Buna-S 9. Polietilen (PE)

10. Vinyl axetat 11. Caosu Buna-N 12. Thuc n: trinitrotoluen (TNT)

13. Benzen 14. Polistiren (PS)

15. Thuc dit c: axit 2,4-iclo phenoxiaxetic

16. Thuc tr su: 4,4-icloiphenyl triclometyl metan (DDT)

33

B. TRC NGHIM KHCH QUAN

Cu 1. S ng phn cu to ca C6H14, C5H10, C4H6 (mch h) v C8H10 (dn xut

ca benzen) ln lt l:

A. 5; 10; 2; 4 B. 5; 5; 4; 4 C. 5; 10; 4; 4 D. 5; 5; 4; 2

Cu 2. Cho cc cht:

CH3 - CH2 - CH - CH3

CH3

CH3 - CH2 - CH2 - CH2 - CH3

(I) (II) CH3

CH3 - C - CH3

CH3

(III)

CH3 - CH2 - CH - CH3

CH3

CH3 - CH2 - CH2 - CH2 - CH3

(I) (II) CH3

CH3 - C - CH3

CH3

(III)

Th t tng dn nhit si ca cc cht l:

A. I < II < III B. II < I < III C. III < II < I D. II < II < I

Cu 3. S ng phn cu to mch h tc dng vi H2 d (xc tc thch hp) thu

c isopentan l:

A. 4 B. 5 C. 6 D. 7

Cu 4. ng vi CTPT C5H10 c x ng phn cu to phn ng vi Br2 v y ng

phn cu to phn ng vi H2. Gi tr x, y ln lt l

A. 8; 9 B. 7; 8 C. 5; 5 D. 8; 8

Cu 5. Hai anken c CTPT C3H6 v C4H8 khi phn ng vi HBr thu c 3 sn

phm, vy 2 anken l:

A. propen v but-1-en B. propen v but-2-en

C. xiclopropan v but-1-en D. propen v metyl propen

Cu 6. X, Y l ng phn c CTPT C5H10. X lm mt mu dung dch brom iu

kin thng to ra sn phm 1,3-ibrom-2-metylbutan, Y phn ng vi brom khi

chiu sng to mt dn xut monobrom duy nht. X, Y ln lt l:

A. 1,2-imetylxiclopropan v xiclopentan

B. etylxiclopropan v metylxiclobutan

C. 2-metylbut-2-en v metylxiclobutan

D. 3-metylbut-1-en v xiclopentan

Cu 7. A, B l ng phn c CTPT C6H6. A c mch cacbon khng nhnh, A lm

mt mu dung dch brom v dung dch thuc tm iu kin thng, A tc dng vi

AgNO3 trong NH3 d to ra C6H4Ag2. B khng tc dng vi dung dch brom v

34

dung dch thuc tm iu kin thng nhng tc dng vi H2 to ra D c CTPT

C6H12. A, B ln lt l:

A. hex-1,4-iin v benzen B. hex-1,4-iin v toluen

C. benzen v hex-1,5-iin D. hex-1,5-iin v benzen

Cu 8. Cho buta-1,3-ien tc dng vi Br2 theo t l 1:1 v s mol, -800C thu

c sn phm chnh l X, cn 400C thu c sn phm chnh l Y. X, Y ln lt

l:

A. 1,2-ibrombut-3-en; 1,4-ibrombut-2-en

B. 1,2-ibrombut-1-en; 1,4-ibrombut-2-en

C. 3,4-ibrombut-1-en; 1,4-ibrombut-2-en

D. 1,4-ibrombut-2-en; 3,4-ibrombut-1-en

Cu 9. Cho isopren tc dng vi Br2/CCl4 theo t l 1:1 th s sn phm (ng phn

cu to) cha brom ti a thu c l:

A. 2 B. 3 C. 4 D. 5

Cu 10. Cht no di y to ra nhiu dn xut monoclo nht khi cho tc dng vi

clo (nh sng)

A. isopentan B. cumen C. xiclohexan D. etylxiclopentan

Cu 11. Cho cc cht c cng thc cu to sau:

CH3

CH3H3C

C(CH3)3

C(CH3)3

CH(CH3)2 CH2CH2CH3

(I) (II) (III) (IV)

Cht tc dng vi brom c nh sng khuych tn hoc bt Fe trong mi

trng hp ch to ra 1 dn xut cha 1 nguyn t brom trong phn t l:

A. I v IV B. I v II C. III v I D. II v IV

Cu 12. Cho cc cht: metan, axetilen, xiclobutan, etilen, toluen, xiclopropan,

vinylaxetilen, but-1-in, but-2-in, xiclopentan, benzen, stiren, isopren. S cht c

phn ng cng vi H2; lm mt mu nc brom; lm mt mu dung dch KMnO4

iu kin thng; to kt ta vi dung dch AgNO3/NH3. A, B ln lt l:

A. 10; 8; 8; 2 B. 11; 8; 7; 3 C. 11; 9; 8; 2 D. 9; 8; 8; 3

35

Cu 13. Cho cc cht sau: etylbenzen; p-xilen; o-xilen; m-xilen, 1,3,5-

trimetylbenzen; 1,2,4-trimetylbenzen. S cc aren cho khi tc dng vi clo

(Fe,t0) thu c 2 dn xut monoclo l:

A. 1 B. 2 C. 3 D. 4

Cu 14. Hn hp X gm 0,2 mol C2H2, 0,3 mol C2H4 v 0,5 mol H2. Cho hn hp

X qua Ni, t0 thu c 16,8 lt hn hp Y. Cho hn hp Y t t qua dung dch Br2

d. Vy s mol Br2 ti a phn ng l:

A. 0,40 mol B. 0,25 mol C. 0,45 mol D. 0,55 mol

Cu 15. Hn hp X gm mt hirocacbon th kh v H2 (t khi hi ca X so vi

H2 bng 4,8). Cho X i qua Ni un nng n phn ng hon ton thu c hn hp

Y (t khi hi ca Y so vi CH4 bng 1). CTPT ca hirocacbon l:

A. C2H2 B. C3H6 C. C3H4 D. C2H4

Cu 16. Hn hp kh X c th tch 4,48 lt (o ktc) gm H2 v vinylaxetilen c t

l mol tng ng l 3:1. Cho hn hp X qua xc tc Ni nung nng thu c hn

hp kh Y c t khi so vi H2 bng 14,5. Cho ton b hn hp Y trn t t qua

dung dch nc brom d (phn ng hon ton) th khi lng brom phn ng l:

A. 32,0 gam B. 3,2 gam C. 8,0 gam D. 16,0 gam

Cu 17. un nng m gam hn hp X gm C2H2, C2H4 v H2 vi xc tc Ni n phn

ng xy ra hon ton, thu c 8,96 lt (ktc) hn hp Y (c t khi so vi hir bng

8). t chy hon ton cng lng hn hp X trn, ri cho sn phm chy hp th

hon ton trong dung dch nc vi trong d th khi lng kt ta thu c l:

A. 20 gam B. 40 gam C. 30 gam D. 50 gam

Cu 18. t chy hon ton 8,0 gam hn hp X gm hai ankin (th kh nhit

thng) thu c 26,4 gam CO2. Mt khc, cho 8,0 gam hn hp X tc dng vi

dung dch AgNO3 trong NH3 d n khi phn ng hon ton thu c lng kt ta

vt qu 25 gam. Cng thc cu to ca hai ankin trn l:

A. CHCH v CH3-CCH B. CHCH v CH3-CH2-CCH

C. CHCH v CH3-CC-CH3 D. CH3-CCH v CH3-CH2-CCH

Cu 19. Khi nung butan vi xc tc thch hp thu c hn hp T gm CH4, C3H6,

C2H4, C2H6, C4H8, H2 v C4H10 d. t chy hon ton hn hp T thu c 8,96 lt

36

CO2 (o ktc) v 9,0 gam H2O. Mt khc, hn hp T lm mt mu va ht 12

gam Br2 trong dung dch nc brom. Hiu sut phn ng nung butan l:

A. 45% B. 75% C. 50% D. 65%

Cu 20. Ho tan ht hn hp rn gm CaC2, Al4C3 v Ca vo H2O thu c 3,36 lt

hn hp kh X c t khi so vi hiro bng 10. Dn X qua Ni un nng thu c

hn hp kh Y. Tip tc cho Y qua bnh ng nc brom d th c 0,784 lt hn hp

kh Z (t khi hi so vi He bng 6,5). Cc kh o iu kin tiu chun. Khi

lng bnh brom tng l:

A. 2,09 gam B. 3,45gam C. 3,91 gam D. 1,35 gam

BI TP TNG HP (Xem CD)

2.1.3. Chuyn 3. Dn xut haloden, ancol, phenol, ete

(Thi lng: 8 tit)

2.1.3.1. H thng l thuyt c bn

DN XUT HALOGEN

a) nh ngha

Khi thay th mt hay nhiu nguyn t hiro trong phn t hirocacbon bng

cc nguyn t halogen ta c dn xut halogen ca hirocacbon, thng gi tt l

dn xut halogen.

b) Phn loi

- Dn xut halogen gm c dn xut flo, dn xut clo, dn xut brom, dn

xut iot v dn xut cha ng thi mt vi halogen khc nhau.

- Da theo cu to ca gc hirocacbon, ngi ta phn thnh cc loi sau:

+ Dn xut halogen no: CH2FCl; CH2Cl-CH2Cl ; CH3-CHBr-CH3; (CH3)3C-I

+ Dn xut halogen khng no: CF2 = CF2; CH2 = CH Cl; CH2 = CH-CH2

Br

+ Dn xut halogen thm: C6H5F; C6H5CH2 Cl; p-CH3C6H4Br ; C6H5I

- Bc ca dn xut halogen bng bc ca nguyn t cacbon lin kt vi

nguyn t halogen.

c) ng phn v danh php

- Dn xut halogen c ng phn mch cacbon nh hirocacbon, ng thi

c ng phn v tr nhm chc.

37

- Tn thng thng: c mt s t dn xut halogen c gi theo tn thng

thng. Th d: CHCl3 (clorofom); CHBr3 (bromofom); CHI3 (ioofom).

- Tn gc - chc: tn ca cc dn xut halogen n gin cu to t tn gc

hirocacbon + halogenua. Th d:

CH2Cl2 metylen clorua CH2 = CH F vinyl florua

CH2 = CH- CH2 Cl anlyl clorua C6H5 CH2 - Br benzyl bromua

- Tn thay th: trong trng hp chung, dn xut halogen c gi theo tn

thay th, tc l coi cc nguyn t halogen l nhng nhm th nh vo mch chnh

ca hirocacbon.

d) Tnh cht ha hc

* Phn ng th nguyn t halogen

RCl + NaOH ROH + NaCl

Kh nng phn ng ph thuc vo gc R: anlyl > ankyl > thm, vinyl

* Phn ng tch hiro halogenua: Quy tc Zaixep: X tch cng H C bc

cao.

* Phn ng vi magie

ete khanR-X + Mg R-Mg-X

ANCOL

a) nh ngha, phn loi

- Ancol l hp cht hu c c nhm hiroxyl lin kt vi nguyn t cacbon no

ca gc hirocacbon.

- C s phn loi anol:

+ Da vo gc hirocacbon ta c ancol no, khng no, thm.

+ Da vo s lng nhm OH ta c monoancol (ancol n chc), iol (ancol

hai chc), poliancol (ancol a chc).

+ Da vo bc cacbon m nhm OH gn vo ta c ancol bc I, II, III.

b) Danh php

- Danh php thay th: tn ca ancol: Tn cacbon mch chnh + ol.

+ Mch chnh: cha nhiu nhm OH nht v di nht.

+ nh s cacbon mch chnh: xut pht t u gn OH nht.

38

CH3 CH C CH2

H2C CH3

OH

CH3 CH2 HC CH2

OH OH

OH

2-etylbut-2-en-1-ol

pentan-1,2,4-triol

- Danh php loi nhm chc: ancol + tn gc hirocacbon tng ng + ic.

(CH3)2CHOH: ancol isopropylic; CH2=CHCH2OH: ancol anlylic

(CH3)2CHCH2OH: ancol isobutylic; (CH3)3COH: ancol tertbutylic

CH3CH2CH(OH)CH3: ancol secbutylic; C6H5CH2OH: ancol benzylic

+ Danh php thng thng

CH2(OH)CH2(OH) Etilen glicol

CH2(OH)CH(OH)CH2(OH) Glixerol

(CH3)2C(OH)C(OH)(CH3)2 Pinacol

(CH3)2C=CHCH2CH2C(CH3)=CHCH2OH Geraniol (dng trans)

c) Tnh cht vt l

+ t0s ca ancol tng theo phn t khi (tng theo chiu di mch cacbon). Cc

ancol mch nhnh si t0 thp hn ancol mch thng. Poliancol c t0s cao hn

monoancol. So vi hirocacbon hoc dn xut halogen c phn t khi tng

ng, ta thy t0s ca ancol cao hn rt nhiu (do ancol c lin kt hiro).

C2H5OH CH3CH2CH3 CH3Cl C2H5F

t0s (

0C) 78,3 42 24 37

+ Cc ancol u dy ng ng tan v hn trong nc do s to thnh lin kt

hiro lm cho cc phn t ancol d dng tch khi nhau v ha tan vo nc. Cc

ng ng t C4H9OH tr ln ch tan c hn hoc khng tan trong nc v gc R

kh ln lm ancol c tnh cht gn ging vi hirocacbon. Tt cc cc monoancol

u nh hn nc, trong khi ancol thm v cc poliancol nng hn nc.

d) Cu trc

+ Nhm OH ancol ni vi 3spC v c cu trc hnh hc gn ging vi phn

t nc. Nguyn t oxi c m in ln hn C, H nn cc lin kt CO, HO

lun phn cc v pha oxi. V vy trong cc PHH cc lin kt d dng b phn

ct theo kiu d li v nhm OH quyt nh tnh cht ha hc ca ancol.

39

+ Do s phn cc nhm OH nn gia cc phn t ancol c lin kt hiro.

Lin kt ny nh hng n nhiu tnh cht vt l ca ancol (trng thi, t0, tnh

tan,)

e) Tnh cht ha hc

* P th nguyn t hiro trong nhm OH

+ P vi kim loi kim: ancol tc dng c vi nhng kim loi mnh nh

Na, K, Li, khng P vi dung dch kim. Cc ancolat kim loi kim c tnh baz

mnh hn NaOH nn d b thy phn to ancol. Cc ancolat tc dng vi dn xut

halogen to ete theo phng trnh: C2H5ONa + ICH3 C2H5OCH3 + NaI

+ P vi axit hu c

CH3

C OH

O

H O C2H

5+

H2SO

4

CH3

C O-C2H

5

O

H2O+

* P th c nhm OH

Vi axit v c mnh: ancol P vi cc axit mnh nh HI, HBr, HCl, H2SO4,

to sn phm th v nc.

H O C2H

5+ H2O+Br H Br-C2H5

KBr + H2SO

4

Trong cc P trn ancol ng vai tr nh mt baz. Kh nng phn ng gim

theo th t: HI > HBr > HCl; ancol bc III > ancol bc II > ancol bc I.

* P tch nc

- Nu dng H2SO4 c 1701800C (hoc Al2O3 400

0C), ancol b tch nc

to anken. i vi cc ancol to nhiu sn phm th sn phm chnh tun theo quy

tc Zaixep: nhm OH tch cng H C bc cao.

- Nu t0 thp hn, khong 1301400C th s xy ra P tch nc gia hai

phn t ancol to ete (P th). Nu c k ancol khc nhau s thu c k(k+1)/2 ete

khc nhau, trong c k ete i xng, cn li ete bt i xng.

* P oxi ha

Ancol bc I, II d b oxi ha bi nhiu cht oxi ha nh K2Cr2O7 (mi trng

axit), KMnO4 (mi trng axit hoc baz), CuO, Ancol bc I b oxi ha thnh

anehit ri axit cacboxylic; ancol bc II cho xeton; cn ancol bc III khng P.

- P c trng ca poliancol: P to phc: cc ancol c 2 nhm OH lin tip

tc dng vi Cu(OH)2 to ra

40

PHENOL

a) nh ngha, danh php

+ nh ngha: phenol l hp cht hu c c nhm OH lin kt trc tip vi vng

benzen. Nu nhm OH gn vo mch nhnh ca vng benzen ta c ancol thm

+ Danh php: tn thay th ca phenol xut pht t tn hirocacbon thm tng

ng c thm hu t ol.

OH OHCH3

OH OH

Phenol o-Crezol 1-Naphtol 9-Antrol

(Benzenol) (2-metyl bezenol) (Naphtalen-1-ol) (Antraxen-9-ol)

b) Cu trc

Nhm OH trong phn t phenol phn cc v pha O, nguyn t oxi ny c

cp electron n. Khc vi ancol, cp electron n ca oxi trong phenol cng vi cc

electron ca vng benzen to nn mt h lin hp, nhm OH gy H +C lm

dch chuyn electron v pha vng benzen. Kt qu l nhm OH cng phn cc,

mt electron trn vng benzen tng ln, c bit l cc v tr 2, 4, 6.

OH..

c) Tnh cht ha hc

* P ca nhm hiroxyl

+ Tnh axit: do H +C ca nhm OH v C ca C6H5, phenol c tnh axit

mnh hn ancol. Tnh axit cng mnh khi c nhng nhm ht electron, cng yu

khi c nhng nhm y electron. Tnh axit ca phenol rt yu nn phenol khng

lm i mu qu tm, khng tc dng vi NaHCO3, phenol b axit cacbonic c y

ra khi mui phenolat.

+ P to thnh ete: mun iu ch ete ca phenol ta khng th un nng

phenol vi H2SO4 c c m phi cho mui phenolat tc dng vi dn xut

halogen theo phng trnh: C6H5ONa + BrC2H5 C6H5OC2H5 + NaBr

Dn xut halogen bc I d P hn bc II v nht l dn xut bc III (trong

iu kin trn s cho P tch).

41

+ P to thnh este: do H +C ca nhm OH nn phenol khng th tham gia

P trc tip vi HCl, HBr, CH3COOH, nh ancol. Mun iu ch este ca

phenol vi axit axetic phi dng anhirit axit hoc clorua axit.

* P vng benzen

+ P th: nhm OH nh hng cc nhm th khc vo cc v tr ortho v

para. Phenol tc dng ngay vi nc brom (dung mi l nc) cho kt ta trng l

2,4,6tribromphenol. Nu P xy ra trong dung mi km phn cc nh CCl4,

CHCl3, CS2, s sinh ra hn hp obromphenol v pbromphenol. Nu dng dung

dch HNO3 c (c H2SO4 c) thu c cht rn mu vng l 2,4,6 trinitrophenol

(axit picric).

+ P oxi ha: phenol rt d b oxi ha ngay c bi oxi khng kh, to cc sn

phm mu, c cu to phc tp.

ETE

a) nh ngha: ete c cng thc chung l ROR, trong R, R c th l gc

ankyl, ankenyl, aryl, Khi nguyn t O ca ete nm trong vng ta c ete vng.

Nhng ete vng c 3 cnh c kh nng phn ng cao nn c xp vo loi ring

gi l epoxi (hay oxiran).

b) Tnh cht ha hc

Ete c P phn ct lin kt CO bng axit (HI > HBr) to thnh sn phm th

nucleophin nhm ankoxi:

ROR + HI RI + ROH t0C

Ancol to thnh nu c d HI s tip tc P to RI.

c) iu ch

+ Cho natri ancolat hoc phenolat P vi dn xut halogen bc I hoc bc II.

+ Cng ancol n gin vo anken.

H+

(CH3)

2=CH

2 + CH

3OH (CH

3)

3C-O-CH

3

2.1.3.2. Bi tp vn dng

A. TRC NGHIM T LUN

Bi 1. Cho cc cht sau:

- A c cng thc C3H8Ox, ch c mt loi nhm chc tc dng c vi Na

42

- B c cng thc phn t C8H10O, tch nc thu c sn phm c th trng

hp to polime, khng tc dng c vi NaOH

- C c cng thc C4H10Oy c th ho tan Cu(OH)2

- D c cng thc phn t C4H8O, mch h, khi b hiro ho c ancol butylic

- E c cng thc phn t C3H5Br3 tc dng vi dung dch NaOH d thu c

cht hu c X c kh nng phn ng vi Cu(OH)2.

Xc nh cng thc cu to c th c ca A, B, C, D, E.

Bi 2.

a) Hy sp xp cc dy cht di y theo chiu tng dn tnh axit: axit picric,

phenol, p-nitro phenol, p-crezol.

b) Hy xc nh k hiu A, B, C, D cho mi cht v gii thch bit chng l 4

hp cht thm: C6H5NH2; C6H5OH; C6H5Cl v C6H6; vi cc nhit si:

Cht thm A B C D

Nhit si (0C) 80 132,1 184,4 181,2

Bi 3.

a) (Trch trong HSG Bc Liu 2004-2005)

Vit phng trnh ca nhng phn ng tng ng vi s sau:

X Y Z Propanol - 2

Tach Cong Kh

b) T etanol vit phng trnh P iu ch cc hp cht sau: metanol, propan-

1-ol, propan-2-ol, phenol, ancol benzylic, glixerol, etylen glicol.

Bi 4. (Trch trong HSG Hng Yn 2008-2009)

C mt ru no mch h X, t chy hon ton 1 mol ru cn t nht

3,5 mol O2.

a) Xc nh cng thc cu to ca X.

b) T n-butan v cc cht v c cn thit, hy vit cc PTP iu ch X.

Bi 5. (Trch trong HSG Qung Bnh 2010-2011)

A l hp cht thm c cng thc phn t C7H8O2. A phn ng ht vi Na d

sinh ra H2 c s mol bng s mol ca A. A tc dng c vi Na2CO3, nhng

khng phn ng vi NaHCO3. Khi tc dng vi HCl to hp cht c cng thc

C7H7OCl, cn tc dng vi Br2 to c dn xut tribrom.

a) Lp lun xc nh cu to A v gi tn.

b) Vit cc phng trnh phn ng xy ra.

43

B. TRC NGHIM KHCH QUAN

Cu 1. Hp cht CH2=CHC(CH3)2CH2CH(OH)CH3 c danh php IUPAC l:

A. 1,3,3-trimetylpent-4-en-1-ol B. 3,3,5-trimetylpent-1-en-5-ol

C. 4,4-imetylhex-5-en-2-ol D. 3,3-imetylhex-1-en-5-ol

Cu 2. Cho cc cht C4H10O, C4H9Cl, C7H8O (dn xut ca benzen). S ng phn

cu to ca cc cht gim theo th t l:

A. C7H8O, C4H10O, C4H9Cl B. C7H8O, C4H9Cl, C4H10O

C. C4H10O, C4H9Cl, C7H8O D. C4H10O, C7H8O, C4H9Cl

Cu 3. C bao nhiu ancol bc 1, bc 2, bc 3, no, n chc, mch h l ng phn

cu to ca nhau m phn t ca chng c phn trm khi lng cacbon bng

68,18%. Kt qu ln lt l:

A. 5; 3; 1 B. 4; 3; 1 C. 4; 4; 1 D. 5; 4; 1

Cu 4. Trong hn hp metanol v etanol c cc loi lin kt hir sau:

... H OC2H5

... H OC2H5

... ... H OCH3

... H OCH3

... ... H OC2H5

... H OCH3

... ... H OCH3

... H OC2H5

...

(I) (II) (III) (IV)

Loi lin kt hiro bn nht v km bn nht

A. (IV) v (III) B. (III) v (IV) C. (II) v (III) D. (I) v (II)

Cu 5. Trong s cac phat biu sau v phenol:

(1) Phenol tan it trong nc nhng tan nhiu trong dung dich HCl

(2) Phenol co tinh axit, dung dich phenol khng lam i mau quy tim

(3) Phenol dung san xut keo dan, cht dit nm mc

(4) Phenol tham gia phan ng th brom va th nitro d hn benzen

Cc pht biu ng l:

A. (1), (2), (4) B. (2), (3), (4) C. (1), (2), (3) D. (1), (3), (4)

Cu 6. Ancol c cng thc n gin nht l C2H5O, s CTCT ca ancol l:

A. 4 B. 5 C. 6 D. 7

Cu 7. ng vi cng thc phn t C3H6O s hp cht mch h bn khi tc dng

vi H2 (xc tc Ni, t0) sinh ra ancol l:

A. 1 B. 2 C. 3 D. 4

Cu 8. A, B, D l 3 ng phn c cng cng thc phn t C3H8O. Bit A tc dng

vi CuO un nng cho anehit cn B cho xeton. Vy D l:

44

A. Ancol bc III B. Cht c nhit si cao nht

C. Cht c nhit si thp nht D. Cht tch nc to anken duy nht

Cu 9. X l hp cht hu c thm c cng thc phn t C8H10O. X c th tc dng

vi Na to ra kh H2, khi oxi ha X bng CuO nung nng to ra sn phm c kh

nng tham gia phn ng trng bc. S cng thc cu to ca X tha mn l:

A. 3 B. 6 C. 5 D. 4

Cu 10. X l dn xut clo ca etan, un nng X trong NaOH d thu c cht hu

c Y va tc dng vi Na va tc dng vi Cu(OH)2 t0 thng. Vy X l:

A. 1,1,2,2-tetracloetan B. 1,2-icloetan

C. 1,1-icloetan D. 1,1,1 tricloetan

Cu 11. Khi cho cht A c CTPT C3H5Br3 tc dng vi dung dch NaOH d thu

c cht hu c X c kh nng phn ng vi Cu(OH)2. S CTCT ca X l:

A. 1 B. 2 C. 3 D. 4

Cu 12. Cht A mch h c cng thc CxHyCl2. Khi cho tt c cc ng phn ca A

tc dng hon ton vi dung dch NaOH un nng thu c hn hp sn phm

trong c ba ancol c kh nng ha tan c Cu(OH)2 to thnh dung dch mu

xanh lam. Cng thc phn t ca A l:

A. C3H6Cl2 B. C4H8Cl2 C. C5H10Cl2 D. C4H6Cl2

Cu 13. Cho cc dn xut halogen CH3CH2Cl, CH3CH=CHCl, C6H5CH2Cl,

C6H5Cl, CH2=CH-CH2Cl, CH2Cl-CHCl-CH2Cl, CH3CCl2-CH3, CH3-CCl3,

CH3CH2CHCl2, CH2=CCl-CH3. S cht khi b thu phn trong mi trng kim

thch hp s thu c ancol l:

A. 2 B. 3 C. 4 D. 5

Cu 14. Cho cc cht etyl clorua, iso-butyl clorua, benzyl clorua, phenyl clorua,

vinyl clorua. S cht b thu phn khi un vi nc, b thu phn khi un vi dung

dch NaOH long, b thu phn khi un vi dung dch NaOH c (t0 v p sut cao)

ln lt l:

A. 2; 4; 1 B. 1; 3; 6 C. 2; 4; 6 D. 1; 4; 1

Cu 15. X, Y, Z l 3 ancol lin tip nhau trong dy ng ng, trong MZ =

1,875MX. X c c im:

A. Tch nc to 1 anken duy nht B. Cha 1 lin kt trong phn t

C. Ho tan c Cu(OH)2 D. Khng c ng phn

45

Cu 16. t chy ancol A bng O2 va nhn thy 2 2 2CO O H O

n :n :n 6 : 7 :8 . A c

c im l:

A. Tc dng vi Na d cho 2H A

n 1,5n

B. Tc dng vi Cu(OH)2 un nng cho hp cht a chc

C. Khng ho tan c Cu(OH)2

D. Tch nc to 1 anken duy nht

Cu 17. Mt hn hp gm C2H5OH v ankanol X. t chy cng s mol mi ru

th lng H2O sinh ra t ru ny bng 5/3 lng H2O sinh ra t ru kia. Nu un

hn hp trn vi H2SO4 m c 1800C th ch thu c 2 olefin. S cht X tho

mn l:

A. 1 B. 2 C. 3 D. 4

Cu 18. Hn hp X gm ancol metylic v ancol A no, n chc, mch h. Cho 7,6 gam

X tc dng vi Na d thu c 1,68 lt H2 (ktc). Mt khc oxi ha hon ton 7,6 gam X

bng CuO nung nng ri cho ton b sn phm thu c tc dng hon ton vi dung

dch AgNO3 trong NH3 d thu c 21,6 gam kt ta. Cng thc cu to ca A l:

A. CH3CH(OH)CH3 B. CH3CH2CH(OH)CH3

C. CH3CH2CH2OH D. C2H5OH

Cu 19. t chy hon ton 0,1 mol cht hu c X l dn xut ca benzen thu c

CO2 c khi lng nh hn 35,2 gam. Bit rng a (mol) X phn ng va vi 500

ml dung dch NaOH 2a (M). Cng thc cu to ca X l:

A. HO-CH2-C6H4-COOH B. HO-C6H4-CH2OH

C. C6H5-CH2OH D. C6H4(OH)2

Cu 20. Thc hin cc th nghim sau:

Th nghim 1: Trn 0,015 mol ancol no X vi 0,02 mol ancol no Y ri cho hn

hp tc dng ht vi Na c 1,008 lt H2.

Th nghim 2: Trn 0,02 mol ancol X vi 0,015 mol ancol Y ri cho hn hp tc

dng ht vi Na c 0,952 lt H2.

Th nghim 3: t chy hon ton mt lng hn hp ancol nh trong th

nghim 1 thu c 6,21 gam hn hp gm CO2 v H2O.

Bit th tch cc khi o ktc v cc ancol u mch h. Cng thc 2 ancol X

v Y ln lt l:

46

A. C2H4(OH)2 v C3H5(OH)3 B. C2H5OH v C3H7OH

C. C3H6(OH)2 v C3H5(OH)3 D. CH3OH v C2H5OH

BI TP TNG HP (Xem CD)

2.1.4. Chuyn 4. Anehit, xeton

(Thi lng: 6 tit)

2.1.4.1. H thng l thuyt c bn

Anehit v xeton u l nhng hp cht cha nhm cacbonyl C=O. V vy

chng c gi l hp cht cacbonyl.

ANEHIT

a) nh ngha, danh php

+ Anehit l hp cht hu c c cha nhm CH=O lin kt vi nguyn t

cacbon (hay nguyn t H) trong phn t.

+ Danh php anehit: tn hirocacbon tng ng + al. Nu nhm CHO

gn trc tip vo vng, ngi ta thm hu t cacbanehit vo tn ca hirocacbon

tng ng (khng tnh nguyn t cacbon ca nhm anehit).

+ Nhng anehit m axit tng ng c tn thng th c th gi tn theo cch

thay axit thnh anehit: CH2=CHCHO: anehit acrylic; CH2=C(CH3)CHO:

anehit metacrylic; CH3CH=CHCHO: anehit crotonic.

b) Cu trc

+ Nguyn t C trong nhm CHO trng thi lai ha sp2

+ Lin kt C=O lun phn cc v pha oxi do nhm cacbonyl quyt nh

nhng tnh cht c trng ca anehit.

c) Tnh cht ha hc

- P cng cc cht nucleophin: do s phn cc lin kt C=O lm xut hin

in tch dng nguyn t C nn anehit c th cng nhiu tc nhn nucleophin

khc nhau. C ch P cng nucleophin: P qua hai giai on:

+ Giai on 1: giai on chm, trong phn mang in tch m ca tc nhn

nucleophin tn cng vo nguyn t C ca nhm cacbonyl.

+ Giai on 2: din ra rt nhanh do anion va mi sinh giai on trc

tng tc vi tiu phn mang in tch dng ca tc nhn hoc ca dung mi to

thnh sn phm. V d:

47

C6H5 CH O C6H5 HCO

C N

++ -

C N C6H5 HCOH

C N

--

H+

nhanh

chm.

- Trong P AN, gc hirocacbon R cng ln (cng y electron) P cng

chm nu cng ht electron P cng nhanh. Tc nhn nucleophin c th l H2O (to

hirat); ancol (to hemiaxetal); natri hiro sunfit (NaHSO3); hp cht c magie

(RMgX); hiro xianua HC N (to xianohirin).

+ Cng nc

C OH

HOHH C

OH

OH

H

H99,9%+

Cc ng ng ca fomanehit cng nc kh hn nhiu.

+ Cng ancol: to thnh hemiaxetal RCH(OH)OR. V d:

CH3 CH O O C2H5 CH3 HCOH

OC2H5

+

78%

+ - ..

H

- Gc hirocacbon trong phn t anehit cng ln, cn bng cng lch v bn

tri. Nu nhm CO v nhm OH cng c mt trong mt phn t v v tr c

th to vng 5 hoc 6 cnh (bn) th P cng ni phn t s xy ra rt thun li.

Nu P gia anehit v ancol theo t l 1: 2 s cho sn phm l axetal RCH(OR)2.

CH3CH=O + 2C2H5OH CH3CH(OC2H5)2 + H2O

XETON

a) nh ngha, danh php

+ Xeton l hp cht cacbonyl c cha nhm CO lin kt vi hai nguyn t

cacbon RCOR.

+ Danh php thay th: tn hirocacbon tng ng + on.

CH3CH(CH3)COCH2CH3 2Metylpentan2on

CH2=CHCOCH3 But3en2on

+ Danh php loi chc: tn cc gc hirocacbon + xeton.

+ Danh php thng thng ca mt s xeton c IUPAC lu dng

CH3COCH3 Axeton C6H5COCH3 Axetophenon

C6H5COC6H5 Benzophenon CH2=C=O Xeten

48

b) Cu trc

Nhm cacbonyl trong xeton tng t nh anehit. Tuy nhin, nguyn t C

trong nhm cacbonyl ca xeton b che chn nhiu hn v in tch dng cng b

gim nhiu bi hai gc hirocacbon.

c) Tnh cht ha hc

Do c nhm C=O nh anehit nn xeton c mt s tnh cht tng t anehit

(cng vo C=O, th nguyn t oxi trong C=O, ). Tuy vy, kh nng phn ng ca

xeton km so vi anehit. Bn cnh , xeton kh b oxi ha v khng c nguyn t

hiro ni vi nhm C=O.

* P cng nucleophin: xeton c kh nng cng tc nhn nhit phn nh

anehit. Kh nng cng ca xeton so vi anehit nh sau:

CH3CHO > (CH3)2C=O > (isoC3H7)2C=O > (tertC4H9)2C=O

* P gc hirocacbon no: nguyn t hiro v tr i vi nhm C=O

trong phn t xeton (anehit cng vy) d b th bi clo, brom hoc iot.

CH3COCH3 + Br2 CH3COCH2Br + HBr

Nu dng d halogen v P thc hin trong mi trng kim, cc hp cht

cacbonyl kiu CH3COR (R: hiro, ankyl, aryl, ) c P cho dn xut trihalogen

CX3COR, dn xut ny b kim ct ngay thnh CHX3 v RCOONa.

CH3COCH3 + 3I2 + 3NaOH CH3COCI3 + 3NaI + 3H2O

CH3COCI3 + NaOH CHI3 + CH3COONa

P trn gi l P ioofom dng nhn bit nhm CH3CO trong xeton hoc

anehit hoc nhm CH3CHOH trong phn t ancol (trong iu kin ca P

ioofom nhm CH3CHOH b oxi ha thnh CH3CO).

2.1.4.2. Bi tp vn dng

A. TRC NGHIM T LUN

Bi 1.

a) Mt anehit A c cng thc n gin nht l C2H3O. Xc nh cng thc

phn t, cng thc cu to, tn ca A.

b) Bng phng php ho hc phn bt 4 cht lng CH3OH, C2H5OH;

HCHO; CH3CHO

49

Bi 2. A, B, C, D l nhng cht hu c mch h c cng thc phn t C3H6O.

a) Vit cng thc cu to v gi tn A, B, C, D.

b) Bng phng php ho hc phn bt A, B, C, D.

c) Vit phng trnh phn ng iu ch A, B, C, D t CH4 v cc cht v c.

Bi 3.

a) So snh t0s ca propan2ol, propanon, 2metylpropen.

b) Gii thch ti sao fomanehit (M = 30) c t0s (210C) cao hn metan (M =

30) (890C); ca ecan2ol (M = 156) (2100C), cn unecan (M = 155) (1960C).

c) So snh tnh tan ca hp cht cacbonyl vi ankan v ancol trong nc.

Bi 4.

1. Vit cc phng trnh ho hc biu din s chuyn ho:

a) (Trch trong HSG Nam nh 2007 2008)

C3H6 C3H6Br2 C3H8O2 C3H4O2 C3H4O4 C4H6O4 C6H10O4

b) (Trch trong HSG Nam nh 2009 2010)

X1 X2 X3(C6H10O4) X4(C9H16O4) X2 + Y1 + Y2 + O2

t0, xt t0, xt t0, xt t0, xt

+ Y1 + Y2 + H2O

2. Vit c ch P ca axetanehit vi HCN v nu c tnh ca phn ng.

Bi 5. (Trch trong HSG Bc Giang 2009-2010)

t chy hon ton 20,16 lit hn hp kh gm hai anehit no, n chc, mch

h X v Y thu c 33,6 lit kh CO2. Nu ly cng lng hn hp trn tc dng hon

ton vi dung dch AgNO3 trong NH3 d th thu c 216 gam kim loi Ag. Bit th

tch cc kh u o 136,50C v 1atm. Xc nh cng thc cu to v tn X, Y.

B. TRC NGHIM KHCH QUAN

Cu 1. S ng phn cu to xeton, anehit ng vi cng thc phn t C5H10O ln

lt l:

A. 4, 5. B. 4, 3 C. 3, 4 D. 5, 6

Cu 2. S ng phn cu to c CTPT C6H12O tham gia phn ng trng gng l:

A. 6 B. 7 C. 8 D. 9

Cu 3. Mt hp cht hu c c CTPT l C4H8O. S ng phn cu to cng H2(Ni)

cho ra ru l x v s ng phn cu to phn ng c vi dung dch AgNO3

trong NH3 l y. Vy x, y ln lt l:

A. 6, 2 B. 3, 2 C. 5, 2 D. 4, 1

50

Cu 4. S ng phn cu to mach h c CTPT C5H8O2 (X) c kh nng trng bc

l:(Bit 1 mol X 4 mol Ag)

A. 1 B. 3 C. 4 D. 5

Cu 5. Cho cc tn gi sau: axeton, propanal, propanol, propanon, imetyl xeton,

anehit benzoic, benzanehit, etanial, anehit fomic, fomanehit, anehit oxalic,

iphenyl xeton. Cc tn gi trn ch s cht l:

A. 7 B. 8 C. 9 D. 10

Cu 6. Xt cc loi hp cht hu c mch h sau:

Ru n chc, no (1); anehit n chc, no (2); ru n chc, khng no 1

ni i C=C (3); anehit n chc, khng no 1 ni i C=C (4). ng vi cng thc

tng qut CnH2nO ch c 2 cht sau:

A. (1), (2) B. (2), (3) C. (3), (4) D. (1), (4)

Cu 7. Cho cc cht sau: etilen, axetilen, propilen, stiren, vinylaxetilen, etanal,

axeton, propin, but-2-in. S cht va lm mt mu dung dch Br2, va to kt ta

vi dung dch AgNO3/NH3 l:

A. 2 B. 4 C. 5 D. 6

Cu 8. Cho cc phn ng sau:

a, CH3CHO + H2(Ni,t0)

b, CH3CHO + AgNO3/NH3(t0)

c, CH3CHO + Cu(OH)2 /NaOH(t0)

d, CH3CHO + ddBr2

e, CH3CHO + O2(Mn2+

,t0)

S phn ng anehit axetic th hn tnh oxi ha v s phn ng anehit axetic

th hin tnh kh ln lt l:

A. 1, 4. B. 2, 3 C. 3, 2 D. 4, 1

Cu 9. Cho s phn ng sau:

0

2 20

H d O ,xtCuO,t

Ni,tX Y Z axit isobutiric .

Bit X, Y, Z l cc hp cht hu c khc nhau v X cha no. CTCT ca X l:

A. (CH3)2C=CHCHO B. CH3-CH(CH3)CH2OH

C. (CH3)3CCHO D. CH2=C(CH3)CHO

51

Cu 10. Axetanehit c th