GIO N GING DY

Trng: Lp: 11 . Mn: Ha hc Tit th: . Ngy: / /20 H v tn GSh: M s SV: H v tn GVHD: Bi 55

PHENOL
I. MC TIU: 1. V kin thc HS bit : nh ngha, phn loi hp cht phenol. Tnh cht vt l, ng dng ca phenol. Cu to, tnh cht, iu ch phenol n gin. HS hiu : Nguyn nhn dn n tnh cht ha hc ca phenol. So snh c nhng im ging nhau v khc nhau v tnh cht ha hc ca phenol v ancol. 2.V k nng Phn bit phenol v ancol thm Vit cc PTHH ca phenol vi NaOH, Br2 (dd) Vn dng cc tnh cht ho hc ca phenol gii ng bi tp. 3.Gio dc t tng Hp cht phenol l cht c, cn cn thn trong th nghim v i sng. II. PHNG PHP V PHNG TIN DY HC 1. Phng php Dim ging, m thoi, gii thch, trc quan, thuyt trnh, gi m 2. Phng tin Sch gio khoa, my tnh, projector III. NI DUNG V TIN TRNH LN LP 1. n nh lp (1pht): Kim tra s s. 2. Kim tra bi c (5 pht) Etanol tc dng vi cc cht no sau y: Na, NaOH, HBr, C2H5OH (H2SO4 , 140oC), CuO, dd Br2. Vit phng trnh phn ng minh ha. p n: Etanol khng phn ng vi NaOH v khng lm mt mu dung dch Brom. 1

2C2H5 - OH + 2Na 2C2H5 ONa + H2 C2H5-OH + HBr C2H5Br + H2O

H SO 2C2H5-OH C2H5-O-C2H5+ H2O 140 C
2 4 o

t CH3 - CH2 - OH + CuO CH3 - CHO + Cu + H2O

0

3. Ni dung bi hc Ni dung I. NH NGHA, PHN LOI 1. nh ngha Thi gian 5 Hot ng ca GV & HS Hot ng 1 GV: Cho HS phn tch s ging v khc nhau v cu to phn t ca hai cht (A) v (C) HS: Quan st v nhn xt: -Ging nhau: +u c vng benzene +u c nhm OH -Khc nhau: +Cht A c nhm OH gn trc tip vo vng benzene +Cht C nhm OH gn gin tip vo vng benzen thng qua 1 nhm CH2 GV: Bit cht A l phenol v cht C l ancol thm, yu cu HS: -Rt ra nh ngha phenol? HS nu nh ngha. Ch : Phenol cng l tn ring ca cht (A). l cht phenol n gin nht tiu biu cho cc phenol. Cht (A), (B) phenol. -Cht (C) c nhm OH nh vo mch nhnh ca ca vng thm th cht khng thuc loi phenol m thuc loi ancol thm. 2. Phn loi C s: Da theo s lng nhm OH trong phn t. 5 Hot ng 2 GV yu cu HS nghin cu SGK 2

OH

OH CH3

CH2 - OH

(A )
Phenol

(B)

(C)

2-metylphenol ancol benzylic (phenyl metanol)

Phenol

ancol thm

Phenol l nhng hp cht hu c m trong phn t c cha nhm hiroxyl (-OH) lin kt trc tip vi cacbon ca vng benzen. -Phenol n gin: C 6H5-OH

- Nhng phenol m phn t c cha 1 nhm OH thuc loi phenol n chc.

OH
OH
CH3
CH3 CH3

OH

OH

phenol o-crezol m-crezol p-crezol - Nhng phenol m phn t c cha nhiu nhm OH thuc loi phenol a chc.
OH OH OH OH OH OH

bit cch phn loi phenol . HS phn loi GV lu HS n c im : nhm OH phi lin kt trc tip vi vng benzen, ng thi hng dn cch gi tn. - Nhm OH lin kt vi C ca vng benzen gi l OH phenol. - C6H5 gc phenyl.

OH

OH CH3

OH

Phenol CH3 2-metylphenol (o-crezol) 4-metylphenol (p-crezol)

catechol

rezoxinol

hiroquinol

Phenol
OH

HO

1 2 3

CH3 1,2 - ihiroxi -4-metylbenzen

II. PHENOL 1. Cu to - CTPT: C6H6O ( M =94) - CTCT: C6H5 OH Hay:
H O

Hot ng 3 GV cho HS nghin cu SGK bit CTPT, CTCT ca phenol. GV yu cu HS phn tch s ging nhau v khc nhau ca hai hp cht:C6H5OH , C6H6 HS phn tch : -u c cha vng benzene -Khc :Phenol c nhm OH trong phn t . GV b sung: ngoi ra oxi cn c cp electron t do b vng benzene ht gy ra hiu ng y electron vo vng benzen lm giu cc v tr octhor(o) v para (p)v lm ngho 3

trn nguyn t O ( lm phn cc lin kt O-H) GV yu cu HS tham kho sgk v tng kt tnh cht vt l ca phenol GV nhn mnh: phenol rt c, khi dy vo tay n c th gy bng da nn phi cn thn khi s dng GV so snh nhit si ca phenol vi etanol, t d on kh nng to lin kt hidro lin phn t ca C6H5OH HS: phenol c nhit si cao hn etanol l do phenol c lin kt hidro bn hn etanol (v do phn t khi ca phenol ln hn etanol) 10 Hot ng 4 GV: t cu to ca phenol, yu cu HS phn tch tnh cht ha hc c th c ca phenol? HS phn tch: -C nhm OH ging ancol nn phenol c kh nng th H ca nhm OH -Phenol c vng benzene , nn c phn ng th nguyn t hiro trong vng benzene. a) Phn ng th nguyn t H nhm OH. Tc dng vi kim loi kim 2C6H5OH + 2Na2C6H5ONa + H2 natri phenolat Phn ng vi dung dch baz. C6H5OH+ NaOHC6H5ONa+ H2O (tan) -Phenol c tnh axit mnh hn ancol, nhng tnh axit yu, yu hn axit cac bonic v khng lm i mu giy qu. GV yu cu HS tham kho SGK Yu cu HS vit ptp ca phenol tc dng vi Na? HS: 2C6H5OH + NaC6H5ONa + H2 GV m t th nghim phenol phn ng vi NaOH HS theo di GV hi: phenol khng tan trong nc nhng li tan c trong dung dch NaOH, iu chng minh 4

2. Tnh cht vt l Tnng chy0C. 43 0 Tsi C. 182 tan,g/100g 9,5g (250C)

- t tan trong nc lnh, tan nhiu trong nc nng. - Rt c, dy vo tay gy bng nng.

3. Tnh cht ha hc - Phenol c phn ng th H nhm OH v c tnh cht ca vng benzen.

phenol c tnh cht g? HS: Tnh axit C6H5ONa+ CO2+H2OC6H5OH+ NaHCO3 GV b sung: phenol l mt axit rt yu( yu hn c axit cacbonic), v khng lm i mu qu tm. GV gii thch: nh hng ca gc phenyl ln nhm OH : gc _C6H5 ht e lm cho lin kt O H b phn cc H linh ng hn H ca OH trong ancol phenol c tnh axit yu ( yu hn H2CO3 ) Hot ng 5 GV m t th nghim phenol tc dng vi dd brom, thng bo sn phm 2,4,6 tribromphenol kt ta trng.. HS quan st th nghim nu hin tng , nhn xt. GV gii thch: nh hng ca nhm OH ln gc phenyl: Nhm OH y e lm tng mt e v tr 2,4,6 P th vo v tr o- , pH O

-nh hng ca vng benzen n nhm OH, l: Vng benzen lm tng kh nng phn ng ca nguyn t H trong nhm OH hn trong ancol ( phenol c tnh axit t/d vi NaOH).
l kt qu ca s nh hng qua li gia cc nguyn t trong phn t.

b) Phn ng th nguyn t H ca vng benzen. - Vi dung dch brom.

OH
Br

OH
Br

+ 3Br2
Br

+ 3HBr

2,4,6 - tribrom phenol ( tra ng)

Phn ng ny dng nhn bit phenol . Ngoi ra phenol cn phn ng vi HNO 3 xc tc H2SO4
OH + 3HNO3 xt, t
o NO2

OH
NO2

+ 3H2O
NO2

2,4,6 - trinitro phenol ( o cam)

c) Nhn xt Phn ng th vo nhn thm ca phenol d hn benzen, iu kin m du hn th vo c 3 v tr. 4. iu ch Sn xut ng thi phenol v axeton : 4 Hot ng 6 GV thuyt trnh phng php iu ch phenol trong cng nghip hin nay. HS lng nghe v ghi chp 5

CH2 = CH - CH3

H+ Benzen

1. O2 kk - CH - CH3 2. dd H2SO4 CH3

OH + CH3 - C - CH3 O axeton

isopropylbenzen (cumen)

Phenol

un no ng va ngng tu

Hoc: C6H6 C6H5Br C6H5ONa C6H5OH Ngoi ra cn c tch t nha than . 5. ng dng -Sn xut nha phenol-fomanehit hay poli(phenol-fomanehit) dng ch to cc dn dng; nha ure-fomanehit dng lm cht kt dnh. -Sn xut phm nhum, thuc n, cht dit c, cht dit nm.

Hot ng 7 Cn phi cho HS nm c li ch v c hi ca phenol.

4. Cng c kin thc. (2 pht) Nhc li tnh cht ho hc ca phenol, so snh vi tnh cht ca ancol. Bi tp: Cu 1: Trong s cc ng phn sau, c bao nhiu ng phn va phn ng vi Na, va phn ng vi NaOH ?

A. 2 B. 3 C. 4 D. 5 (p n B) Cu 2: nhn bit cc cht lng sau: phenol, ancol benzylic v benzen c th dng thuc th l: A. Dung dch Br2 B. Dung dch Br2 v Na C. Dung dch KMnO4 D. Na v dung dch NaOH (p n B) 5. Dn d (1 pht) Bi tp v nh t 1- 6/ SGK Xem trc bi mi.

Gio vin hng dn Ngy duyt: Ch k

Ngy son: Ngi son