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2011-2013


2011-2013 12013 18

A C10H18O C A 22013 27. :
R1COOCH2 R2COOCH3ROH R3COOCH2 R1COO R R2COO R R3COO R CH2OH CHOH CH2OH

B

D







. A. B. C.

D. C 32013 28. A. 55-60X B. C. 1,2- D. 2,4- ݡ H D D D 42013 112 C5H10O2 A15 B28 C32 D40

C5H10O2 ç H-COO-C4H9 1 4

CH3-COO-C3H7 C2H5-COO-C2H5 C3H7-COO-CH3

1 1 2 5

2 1 1 8

5 8 58=40 52013 13 58 CO2 H2O A.4 B.5 C.6 D.7

CnH2nOX 58-16=42 3 C3H6O O, 58-32=2 6 C2H4OXx B

6 [2013 ??5] X Y ( )

A1mol X 3mol H2O B1mol Y 2mol X CX HBr C24H37O2Br3 DY Y 1molX 3mol 3molH2O A Y -NH2 -NH- H X X X 1molY Y

3molXB X HBr -Br X -OH C Y ܧD B 72013 7.ۧ A Na2CO3 BC5H12 C D B C D ֧A 82013 12.

A. B. FeCl3

C. NaHCO3 D. NaOH ɧ





( ) Na NaOH Na 2 CO 3 NaHCO 3 CH 3 COOH H 2 CO 3 C 6 H 5 OH HCO 3 H CH 3 COO HCO 3 C 6 H 5 O CO 3 2 NaHCO 3 A. B. C. D. NaOH B C 6 H 5 OH Na 2 CO 3 C 6 H 5 ONa w w w w

92013 1ݧ٧ A B C D

[]CD []D 102013 7ާ A B C D []ABC A B C []D 112013 9 A2- C2,2- B D2,2-

[] AC 2 BD 1

[]BD 122013 1.2013 4 24 A. B.֧ۧ C. D. A ۧB C NaOH NaOH D D 132013 2.NH4OCN [CO(NH2)2] A. C. B. D.

A B CON2H4C D C 142013 10. A. C. A B C D D D. B.

152013 12.

A. B.

3--1,3- 2- 2- 3-

C.CH3CH(C2H5)CH2CH2CH3 D.CH3CH(NH2)CH2COOH

A ˦ʧ 2--1,3-B 1-C 3-D 3-D

16 2013 10 A C7H6O5 B C D 7H10O5 C A B

C H+D C 172013 10

A -4,4-

2,3,5,5-

B C KMnO4

D



A 2,2,4,5- -3,3-B C7H6O2 C6H6 2 CO C D 182013 7

A Bæ C D A 192012 11 āq A. FeCl3 B. KMnO4 C. D.1mol 1molNaOH

A. FeCl3 BC. KMnO4 D. 1mol 2molNaOH BC 202012 2) A. B. C. B CO H2C D A 212012 5 C10H14 A2 B3 C4 D5 C10H14 C6H5C4H9C4H9 4 D.

4 C

22 2012 18-I(6 ) ׳ 31 A B@ C D A @ B
H3C CH3

3 H

6:4=3:2 C BD

232012 7ۧ A C A HBr B ɉ^ D BC4H10

C D D 242012 7 A B CHON C CO2 H 2O D ɧ A ,A B CHON B C CHO N Cl CO2 B H2OC D 10-7m 100mm,D 252012 11

A 256-4-



B
OH OH OH H OH H H H H OH
CH 2OH

C

H



H OH

O H OH H H

OH H



OH

OH

C6H12O6 Cm(H2O)n
O OH O O OCH3 CH3 O

D1.0 mol

O



5.0 mol NaOH A D 5 6 ˦ 2 ˦ 2362 53. 5>3 236-4- A

˦ 2338 8˦ 2277 8232. 2<3 227 78 2D D

i D D (ii)

ާ DD

CH2CH3

,

, ߧ˦ 3,6--7- 4,7--3 B ̧֦B C C D mol 1.0 1mol

3mol 1mol 1mol 5.0 mol NaOH D 26 2012 9M:
HO S N COOH S
ATP ??

-CO2 O2 ??

HO

S

N S

O +



A. C. B 272012 7 A B C D. 7 B.

D 28 2012 10 A KMnO, B Cl2 Br2 C C6H12O6 D Na H2 KMnO4 A ; Br2 B C D 292012 13

A B C 1mo1 470.4 D 1mo1 240g A 2 B 1mo1 470.4 C 1mo1 3mol 480g .D 302012 11 A.

B C. D. ۧ 312012 8 A 95% B C D A 75%C D k 322012 10 C5H12O ( )

A5 D8

B6

C7

Չ3 ֧ 3 + 4 + 1 = 8 332012 12 26 1 C
2H4

9 C
4H8

2 C
2H6

3 C2 H6O

4 C2 H 4O
2

5 C
3H 6

6 C
3H 8

7 C3 H8O

8 C3 H8O
2

10 C4 H10

AC7H16 DC8H18O

BC7H14O2

CC8H18

2 4 26 = 46 + 2 24 C7H14O2 25 C8H16

342011 11 A1

A. KMnO4 B.1mol X 2molH2 C. A1 NaOH D. X A1ɧ A. ܧ KMnO4 B.1mol X 2mol 1mol 3molH2

C. A1 NaOH D. X ^ A 352011 11
H N NH2 CH2 CHCOOH CH3O H N O CH2 CH2 NH C CH3

Aզæ B pH C D Aæ

Bæ ^ C D D 362011 7 A. B.2,4- C.CH3CO18OC2H5 CH3CO18OH C2H5OH D. 4 A 2,4- ɧ

B ֦ CH3CO18OC2H5 CH3COOH C2H518OH C

2 4 D C 372011 8ۧ A B C12H22O11 CCH3 H D

COOH H CH3COOH H++CH3COO 2

C 382011 7 A. B. C. NaOH [ D. A B NaOH C D C

392011 11 A. NaHCO3 CO2 B. C. D. NaHCO3 CO2A B C ٧ D B 402011 NM3 D58 ŧ

NM3 D58 A. NaOH B. C. D. FeCl3 ݧ NM3 D58 NaOH A B NM3 D58 ܧ C FeCl3 D C

412011 C5H11Cl ɧ A.6 B.7 C. 8 D.9

C5H11Cl 5 3 12 3 4 2 4 2 12232 31 3 4 231 C5H11Cl 8 C 422011 ٧ CH3CH=CH2+Br2 CH3CH2OH CH3CHBrCH2Br

CH2=CH2+H2O CH3COOCH2CH3+H2

CH3COOH+CH3CH2OH O C6H6+HNO3

C6H5NO2+H2O

A. D.

B.

C.

B B 432011 ݧ A. []A   442011 ݧ B. C. D.

A.

B.

C.

D.

A B C 1 ˗D ˵[]CD 13- 6 13- 10 12 ˨ 45(2011 II 7) A B 3- C D 3- 姳

D 462011 HCHO+NaHSO3 HO-CH2-SO3Na

DD A B C D ݧܧ֧ B 472011 A B C

D AB C C 48 2011

A2

B3

C4

D6

13 C 492011 25 101kPa 32mL, 72mL A. 12.5% B. 25% C. 50% D. 75%

2mH2O V

4CnHm(4n+m)O2

4nCO2

4 4+m 32 72

4n+m

4n

m5 5 6 Q

B



1 2013 10. G



.G

A~F ݡ



1G



G

2 3B 4~ 5



6 E

OO ^ 1C6H10O3
CH3C=CH 2 2 + HBr CH3 CH3CHCH2Br CH3



32--1- 4
CHO CH3CHCHO + OHCCOOC2H5 CH3CCHCOOC2H5 5CH3 CH3 OH

6CH3COOCH2CH2OOCCH3 CH3CH2OOCCOOCH2CH3 CH3OOCCH2CH2COOCH3

A B B G F E D E D C C C

2(2013 2)38.[ 5 ]15 11H12O3 C E H

A
B RCH=CH2 H O2H6 /OH
2 2


RCH2CH2OH

F 1 A _________ 2 D _________ 3 E ___________ 4F G , __________ 5I ___________

6I J I 14J NaHCO3 CO2______ J 2:2:1 J

ݏ pݧ 1A C4H9Cl A (CH3)3CCl 22 2AB B (CH3)2C=CH2BC C (CH3)2CHCH2OHCD D (CH3)2CHCHO 3DE E (CH3)2CHCOOH C4H8O2

4F C7H8O

F



1:2 2 H Cl

5FG GH CHCl2 CHOHI I

6J I 14 J I C NaHCO3 CO2 COOH CH2CH2CHO COOH CH(CH3)CHO CH2COOH CH2CHO CH2CH2COOH CHO CH(CH3)COOH CHO HOOCCHCHO CH3 63=18 ^

2:2:1 122ώ@ 2(CH3)2CHCHO 3C4H8O2

4



5 618

32013 138.[ 5: ](15 ) G ɡ:

: A 100-110 I mol A 72g C D Na2CO3 4

1A __________ 2 B C _______________ 3E ___________, F _______________ 4G ______________ 5D H H _______________________ 6F FeCl3 ____ 2 5 2:2:2:1:1 ________( ݧ 11molA 72g 4mol A 8 B C B A B A

A A D Na2CO3 D 4 D ٦ D E E D F C F G

C 1 2 B

3 7H5O2Na C 4

5 6

4[2013 ??10](15 ) E M ()

H2O CH3CCH CH3CCH2 A B

OH

O CH3CCH3 X D OH

O E O C2H5OCOC2H5 C9H6O3 M

O O C6H5OH CH3COCCH3 C6H5OOCCH3 G J

CCH3 O L

10

(1) A

AB

(2) DE X Cu(OH)2
2 (4) L Q Q



(3) GJ

Cl

NaOH

K2Cr2O7H+



R(C8H7O2Cl)

S

TT

Q

(5) 10 (6) LM C6H5OH+C2H5OCR C6H5OCR+C2H5OH R1CCH3+C2H5OCR2 R1CCH2CR2+C2H5OH M

15 1 C6H5CHO+2Cu(OH)2+NaOH 3-COOH 4

2

C6H5COONa+Cu2O+3H2O

5

6

1A AB H2O 2 DE E D X E H2O X 3G G J ܧ-COOH4 L Q T Q H Cl RS 56 M M

52013 26.16 F

1B

E ܧ

2 C E F



3 3 4 1



5

a. A cE

b. D d. F

1HOOC(CH2)4COOH 2

CH3OOC(CH2)4COOCH3+2HOCH2CH2NH2 HOC(CH2)4CONHCH2CH2OH2CH3OH

HOCH2CH2N

3 4 5abd A C B C C F C ? F Iա ˧ݝp

6 2013 8 E E

1 A 21.6% A ___________ A A ______________ 2 B Cu(OH)2 _______________________________ 3 C _____ C _______

4 _________________D _______________________ 5 _________________________ a. 6 b. 6________________ E _______________________________ 1A 21.6% A A 74-OH 17 57C4H9 1 C4H10O 2B Cu(OH)2 CH3CH2CH2CHO2Cu(OH)2 NaOH


CH3CH2CH2COONaCu2O3H2O

3B 2 2

C

D H2 4D 5 46

6 E

1C4H10O1 2CH3CH2CH2CHO2Cu(OH)2 NaOH


CH3CH2CH2COONaCu2O3H2O

32 4 5

6

72013 2517 P

1A ____________

2 a ________________ 3BC _____________ 4 D 2 D ___________ 5EF ___________ 6F _____________ 7 P ________________ 12CH3COOH H (3) 4 CH3COO

5 6

7
2



A 2 ? 8 ? 2 ? 10 =4 C A a Ba CH3COOHA B

B C C D 2 D -NH2 -OH NaOH D D E E -CHO E

i E F F

G G 2 F æ 1 G

ii P



82013 338 66

1 B 2D 3 D NaOH 4 F G H A H2 B HCl C D F G H-66 1B C4H8O CH3CH2CH2CHO(CH3)2CHCHO 2D 1,4-CH2ClCH2CH2CH2Cl

3 NaOH AgNO3 Cl- 4nHOOC(CH2)4COOH+nNH2(CH2)6NH2


HO

O O C (CH2)4 C NH(CH2)6NH H(2n1)H2O 1CH3CH2CH2CHO(CH3)2CHCHO 2CH2ClCH2CH2CH2Cl 3HNO3AgNO3 4 nHOOC(CH2)4COOH+nNH2(CH2)6NH2


HO

O O C (CH2)4 C NH(CH2)6NH H(2n1)H2O 92013 30.16

1 2

1mol molO2

C10H11C1 NaOH ______

3 NaOH 1112 _______ 4 CH3COOCH2CH3 CH3COOCH2CH3 Cu O2 ____________

5



1

6 10 3 C6H10O3 1mol 6molCO25molH2O 26+153 2=7mol2 ܧ



3

:::

4 ` ܧ

5



C6H10O3 2 1 7mol 4 3 5





102013 29 Cl2
FeCl3 A B NaOH/H2O C HCl D Fe HCl E

F C7H6O3 OH

CNH O

OH


NO 222 Fe HCl NH2

2

1 A.1 mol 2 molNaOH C. D. B.

2 A 3 B

B ______________ C

__________________________________ 4 F _____________________________ 5 F ____________ 3 6 O CH CH OH
2 3 2

CH3CHO



CH3COOH

H2SO4

CH3COOCH2CH3

F A C E B D



()1 mol 3 mol NaOH

1mol Br2 4 molBr2 1CD 2 3 O2N
Cl
H2O

O2N

+ 2NaOH + NaCl+H2O 4 5 CHO
HO OH HO CHO OH HO

ON aa

HO CHO OH CHO OH

6

֧ ݧ

ݡ

112013 10



AC5H6 B Diels-Alder

Diels-Alder

44. Diels-Alder A



45



46.B Cl2 1,2 HCl 2 CH2=CHCOOH 47. 44 - 46 47 451,3,5-

44 1,3- Diels-Alder

C9H12 B 1,3-A 45 C9H12

8 2 3 3 1,3,5--46 B 1,3- 2- CH2=CCl-CH=CH2 4



NaOH Ag Cu 2013 12





֦

48. 49. 50. A B

51 C K2CO3 52. C 3 53.

48HNO3 FeBr3 49

50



51HCl

52



53

KMnO4 -CH3 -COOH -NH2 C7H8 HNO3

KMnO4 A A FeBe3

Br2 ˧-Br





B B

B



HCl HCl -NH2 K2CO3 HCl HCl -NH2

C6H13NO 3

-CH3 -C(CH3)3

122013 2- 12-

2 A 2- A [] 1 CH3CH=CHCH3+H2 2 CH3CH2CH2CH3 A A

[]2A  4

3

132013 32.[-](13 ) M

1 A _______ a. 2M ____ CB ________ b.Br2/CCl4 c. d.KMnO4/H+

3 A M 5 B C10H13Cl NaOH C10H13Cl ______ 6C E a.OCH3CH3 E __________________ 1bd 2 3 4 5 6 b. ______

4 B C _____

ݧ 1A Br2 bd 2M BD DB C C

B 3 A

4B C B C 5ݨ B C10H13Cl 6C CH3CH2O CH2CH

E



14 2012 17(15 ) H ɡ

(1) A () (2) ()



(3) B

I. II. 7 III. FeCl3 (4) DE X X (5) ()

ɧ

(1) (2) (3) (4) (5)

H ݧ ա

152012 17(9 ) 12

l40 1,2

ۧ 1,2-

g -3 cm 78.5 0.79

2.2



0.71 132 34.6 9 -1l6

l30 (1) 170 () a. b. c. d. (2) C () a b c d (3) (4) 1 2- (DD) (5) Br2 () a b c d (6)

(7) D (1)d (5)b ()

(2)c

(2)

(4)

(6)

(7) 1,2-() (1)D l40 170 (2) C D ܫ (3)D 1,2

(4)1,2- (5) Br2 I2 12- (6)( ) (7)

162012 18-II A C5H8A ( ) (14 ) A C5H8A ()

(1)A (2)B (3) (4) (5)C (6)A (C=C=C) է

(1) ) (2) C5H8O2

21,3(

(3) (4)

(5) (6)6 (1)D A C5H8 A 21,3

(2) D



B B

C5H8O2 (3) Br2





(4)(5) DC C



C Br

DNaOH/H2O (6) 6

192012 2516 X Z Y W X Y A W 1 X L K 2 Y nsnnpn+2 Z 23 12 W W _____________

___________________

2 X Y ____________( );X Y ______________ 3 4 Z2Y2 XY2 ç ________________. _____________XY ________________ 4
2e
2 2 2


2



H 2O

2Na O 2CO ===2Na CO O 2e [
2 3 2


2- 1,2,4,5- CH3COOHHCO3===CH3COOH2OCO2 ը X Y

ZW CONaFe Fe 4 3d64s2 2 X(C)Y(O) X Y H2O Na2O2 CO2 2Na2O2 2CO2===2Na2CO3O2 Na2O2 CH3CH2CH3CH3CCH CH O æ HCO3 HCO3 CH3COOH .20 2012 31[-] 13 p-xylene PX 1 PX 2PX

3DEHP A PA ^

B 2 B D

C DEHP 4F B a b FeCl3 c F NaHCO3 C12H16O3 B C 2012 2914 A

C8H8O2C 2 B GG 172 55.8 % 7.0 % ^
A
1) H2O / NaOH 2) H+ Br2 / P 1) H2O / NaOH 2) H
+

B C

D

E

F

H2SO4

G

1 G 2 A

3 FG

4 C FeCl3
C C OH



5 G 1 1 G 172 55.8 % 7.0 % G CHO C (17255.8 %)/12 = 96/12 = 8 7.0 %/1 = 12/1 = 12 O172 C 96 C 12/16 = 64/16 = 4 G C8H12O4 2 AC12H16O3 B CC8H8O2 A H 172

CC8H8O2 2 C

B C4H9OH B G

B D C3H7COOH

E C3H6BrCOOHE C3H6(OH)COONaH F(C3H6(OH)COOH), G

C8H12O4 F G G ^ G

F A

B

3FG 4 FeCl3
HO COCH3 HO CH2CHO
C C OH

C 8H8O2 C

HO

OCH=CH2

HO

CH O

CH2

5 G 14 1C8H12O4 2 CH3 3 2 (CH3)2CCOOH
OH
COOCH2CH(CH3)2



O


O O

O

+ 2 H2O

4
HO COCH3 HO CH2CHO

HO

OCH=CH2

HO

CH O

CH2

5

O CH3 C C O CH3

n

212012 28(16 ) M ١.
CH2 CH3 Cl2 NaOH CH3 C CH2 C4H8Cl2 C4H7Cl NaCN CH3 C CH2 CN A B D E CH2

HOOC C CH2 CO OH
M

1A 2BD 4 CH2 CN M
CH2




NaOH

3M Q Q



CH COONa + NH
2

3

, E

E

ClCH2 C CH2 CN
G

Cl2

NaOH


H

O2


J




L



M

EG JL C(OH)3 GH



COOH + H O
2

E

M

28 NaOH 1 2 [

3 4







292012 3014 -ݧ



1

I ______________

2

Br2

______________

C7H5OBr 3 ______________

4



______________ ___________

5

V V

___________

302012 33(8 )[ ]


P()
(H3C)3C (H3C)3C

A(C4H10O)



B(C4H8) C(C6H6O)

HO (H3C)3C

CHCl3NaOH H

HO (H3C)3C

CHO

[Ag(NH3)2]OH F H D E(C15H22O3) P(C19H30O3)


R + R2C=CH2 C R CH3 (R );

A F A F (1) AB GC4H10) ,G B

(2) A HBr H H

(3) C a. d. (4) P NaOH ) A 3 A AB
CH3 C CH3 CH2

b. FeCl3 c. NaHCO3

A B



G 2-(2) H A HBr
Br

CH3

C CH3

CH3 C



FeCl3 FeCl3 C(4) F A 1 F CH3CH2CH2CH2OHP E F

(1)();2- 4 () bd

31 2012 2714 CHO+(C6H5)3P=CHR CH=CHR + (C6H5)3P=OR W ݧHOOCCH=CH CH=CHCOOH

MXYZ

X W NN 168 1W A. D. W B. C.

2

3 X W N 5 A C D3 162 4 3 X

HOCH2CH2OH+HOOCCH=CHCH=CH

COOH

+2H2O(3 )

HOCH2CH2CH2OH(3 ) OHC=CHO+2(C6H5)3P=CHCOOC2H5 2(C6H5)3P=O+H5C2OOCCH=CH CH=CHCOOC2H5(3 ) W C2H5OH X Z C2H5OOC CHCHCHCHCOOC2H5 ϧ Y OHCCHOX HOCH2 CH2OH X W 165 N X HOCH2 CH2OH (1)W (2)
O C





W 16 (3)X W H2O

(4) HOCH2CH2CH2OH (5) 32 2012 2916 1 A. D. 2 pH B. C .

3 1molCH4 160.1kJ 1molCH4 802.3kJ է 4 CO2 M C7H5O3NaM NN M OO N A B C(3 ) Ca(HCO3)2 (2 ) Ca(HSO3)2+O2=CaSO4+H2SO4(3 )

CaS(s)+2O2(g)=CaSO4(s)H=962.4kJ mol
1

(3 ) (2 ) 6(3 )

է (1) CO2 SO2 (2)CO2 CaCO3 Ca(HCO3)2 (3) CH4(g)CaSO4(s)CO2(g)2H2O(g)CaS(s) ?H=160.1 kJ 1 mol CH4(g)2O2(g)CO2(g)2H2O(g) ?H=802.3 kJ 1 mol CaS(s)2O2(g)CaSO4(s)
1

?H=962.4 kJ mol

(4) M

M

N C7H6O3













6

33 2012 818 a G

RCOOC2H5 A ________________ A ZC7H12O3 Z _______________________________________ _______________________________

B _________ B _____________ 2 (4) B CE F __________________________ C D ______________________________________________ __________ Y ______________________ EF G ___________________________ G H2O 4 H H ________________________

ݝp اݧ 2 A 4 AZ Z

(3)BC8H14O3 2 4 BCEF 5CDC NaOHC -COOHNaOH

C

6Y

G



7EFG -COOH-COOCH3-OH NaHCO3(Na2CO3)Na 8GH2O





H

34 201230 15 AC11H8O4 B C 1 B C2H4O2 B ________B D ________________________ ________ B 2

________________________ C 180 60.0 4.4 C ________ 3 C ˦ C (4)A

(1)CH3COOH CH3CH2OH

CH3COOH+

CH3COO CH2CH3+H2O

HCOOCH2CH2CH3 (2) C9H8O4 (3) CH=CHCOOH

HCOOCH(CH3)2

4 1B C2H4O2 B CH3COOH 3COOH CH CH3COOH+ CH3CH2OH CH3COO CH2CH3+H2O B HCOOCH2CH2CH3 HCOOCH(CH3)2 2C C ܧ 180 60.0 9 4.4 8O 4 C C9H8O4

3C ˦ C

4A pݧ էݧ ݞT ا՞T 35.2012 28 (17 ) PMnMA :

:

1 B B (CH3 ), CHCI A B A (2) 1.08g C 3.45 g E Br2 CC14 . F C I (3)()

a B c D E

b. C

d. E

(4) G 3 3:2:1 .G NaHCO3 CO2 II

1 B B H2 B B

(CH3 )2 CHCl





2 F F E F E D C 1.08g C 3.45 g C 4 a

b D E c d 4G NaHCO3 CO2 G

PmnMA





362012 2815

/gcm
-3

3.10

1.50

0.88

/ (1) a

80

59

156

15 mL b 4.0 mL ^ a ɧ (2) a 10 mL ħ 10 mL mL10 NaOH 8 10 mL NaOH ި ^ d

(3)ݧ ӧ A D (4)a A25 mL D500 mL B50 mL C250 mL B C

(1) HBr (3)

HBr Br2 (4) B

(2)

HBr Br2 C

38 2012 38 15 ( )



D F 11 (1)A (2) B C (3)D (4)F (5)G

(6)E ܧ 221 ()

3 3 10 13 3 2 4 39.(2011 1715 )



1A

2C 2 3 C

H2

5 4 C ӧ E C23H18O3E E 5



ݧ ԧ

pݧ ա A A ܧ H2 5 C E E A C

1A O2 2

40 2011 2914
HO OH HO




NaBH4 B C C9 H10O4 / C10H12O4 CH OH C9 H12O3 3

A

CH3 OH

HBr

D
C9H11O2 Br
CHO Li



BBr3

F
C17H18O3

E C17H20O4

H2O CH3 O



RCH2 Br COOCH3

Li

R'CHO
CH2 OH

H2 O

OH RCH2 CH R' CH2 OH



NaBH4 CH3 OH
OCH3

BBr3
OCH3 OH

1 _________________________ 2 CD ____________ EF ____________ 3 A FeCl3 NaHCO3 CO21H -NMR_____ ______________ 4 AB ____________________________________________ 5D________________ E___________________ 6CH3 O
CHO

ɧ

______________________________________________ _________________

A 5
CH3 O CH3 O COOCH3 CH3 O CH3 O CH3 O

A
CH3 O

COOH

B

C

CH2 OH




CH3 O

D
CH3 O

CH2 Br

E

CH3 O CH3 O

OH CH2 CH

OCH3




CH3 O

F
CH3 O

OCH3



1 2 3ݧ H-NMR 4 H2O

5 6 1C14H12O3 2 34 1U1U2U6

4 5

CH3 O COOH + HO CH3 CH3 O
CH3 O CH2 Br CH3 O



CH3 O COOCH3 + H2 O
OH CH2 CH

CH3 O

HO

CH3 O CH3 O

OCH3



6HO CH2

CHO

CH2CHO

CH3

O O CH

41.2011 2617 G

1 A

A ܧ C

B

2C NaOH

3X E X ܧ X

4FG

5G a. c. 1 A d.. b.

A CH2=CHCOOH CH2=CHCOOH CH3CH2COOH 2 C C 2 C C NaOH 3 X 2 2 CH2NH2 3 2 1 13 5

4FG 5 abc d 1 CH3CH2COOH 22

3 4 5abc

422011 2817 D PVB



1A A 2A B

3C B C 4E Br2 CCl4 N A a. b. c.

5PVAC

6PVAc 1A C2H4O A A 2 ֧ա

3 C C C B B C C

4 PVB N CH3CH2CH2CHO E Br2 CCl4 E 2 E CH3CH=CHCHO E F F CH3CH2CH2CH2OHF N

5 C D M PVB N PVA PVAC CH3COOCH=CH2PVAc

1 2

3 4a

b

c 5CH3COOCH=CH2 43. (2011 3113 )

է





(1)____________ ___________ a. Br2/CCl4 (2)ا _______ (3) AD : b. c. KMnO4

A ___________ X ___________

4 5 110 FeCl3

1 2 CH2CHCH2CH2COOH 3 12

4 CH2CH2+HCl CH3CH2Cl



5 FeCl3

ܧ 94 110 9416 1 ac

2CH2CHCH2CH2COOH 3C6H12O6Br2/CCl4 4 5 44.2011 3016 +CH3CH2Cl HCl



1____________ _____________ 2 _____________ 3 ____________ NaHCO3 CO2 ___________________ 4 1 2 1 ` `_________________

51

1





____________1mol ______molH2 ݨ ݧاէ 1 C5H8O4 § 2 H3COOCCH2COOCH3+2NaOH CCH2COONa 2 HOOCCH2COOH HOCCH2CHO HOCH2CH2CH2OH HOCH2CH2CH2OH+2HBr O 3 NaHCO3 CO2 HOCCH2CHO CH2 CHCOOH


2CH3OH+NaOO

CH2BrCH2CH2Br+2H2

4`

5 2 CC 1 1 2 1 1mol 8molH2 1C5H8O4 H3COOCCH2COOCH3+2NaOH CCH2COONa 2 HOCH2CH2CH2OH+2HBr O 3HOCCH2CHOCH2CHCOOH




2CH3OH+NaOO

CH2BrCH2CH2Br+2H2

4 5

8

45.2011 338 R.F.Heck Heck 2010 X R Heck M

1M ______________ a. b. d. c.

2 H2SO4 F KMnO4 C F F __________ D G G __________

3 A B A _______________ 4E K FeCl3 K NaOH __________ 1M ܧ a d 2 M D E CH2=CHCOOCH2CH2CH(CH3)2

B C C H2SO4 F KMnO4 F C B HOCH2CH2CH(CH3)2CH2=CHCOOHC F F (CH3)2CHCH=CH2D

GG

3AB CH2=CHCHO) A A 4 K FeCl3 K ܧ K K , K

NaOH 1ad 2(CH3)2CHCH=CH2 3 4

46.2011 18

I. F

1A 8.8g A NaHCO3 2.24L CO2A _____________________________________________ 2 A ____________________________________________ _____________ 3B ɧ BC ____________________________________________ ______________ 4C+EF ________________________

5 A F A______________________ F__________________________ 6D ___________________ ab a ______________; b___________ . C H

7C ? G _____________________. 8 G ? H _______________________ 1 RCOOH+NaHCO3=RCOONa+H2O+CO2 2.24L CO2 0.1mol A 88g/molCOOH 45g/mol 43g/mol C3H7 A C4H8O2 2 C4H8O2 HCOOCH2CH2CH3 HCOOCH(CH3)2

3 B (CH3)2CClCOOH A (CH3)2CHCOOH BC : (CH3)2CClCOOH+C2H5OH (CH3)2CClCOOC2H5+H2O 4 C E


534 6 ܡ D ab NaOH 7 (CH3)2CClCOOC2H5 C G CH2=C(CH3)COOC2H5 G H



87 1C4H8O2 2HCOOCH2CH2CH3


HCOOCH(CH3)2

3(CH3)2CClCOOH+C2H5OH (CH3)2CClCOOC2H5+H2O 4 5(CH3)2CHCOOH 6Cl2 8 NaOH 7

47.2011 16 GB2760-2011Ǩ G W ١ 1G

A CH2 A E 2W G . A BD E

JL __________ J MQ Q _________CC CH

Q Z ROH+HOR




ROR+H2O



MQT T W 1 ݨ 1 CH2 A A ܧ A ֧ A E ҁ E 2 3 13

2J 2 HCl CH3CHCl2 J

Q 2 CH3CHO CO C H CC Z HOH2CCH=CHCH2OH W T 2 MQ T 2CH3CH=CHCH CHCHO+O2 1 OH


2CH3CH=CHCH

CHCOOH+2H2O



2 CC 2CH3CH=CHCH CHCHO+O2




2CH3CH=CHCH

CHCOOH+2H2O CH3CH=CHCH CHCHO+2Cu(OH)2


CH3CH=CHCH

CHCOOH+Cu2O+2H2O

48.2011 15





A B FeCl3 1 _______ 2 A ___________A __________ 3 B C ___________

4 B ܧ______ _______ 5 D ܧ______ ________ CO2 _________ 1 C9H6O2 2 A A 2 3B FeCl3 B 2



4 C7H8O

2 5 D

˦

CO2 2 1C9H6O22

3 44 2 54 49.2011 8

1 A _______ 2 B A C ________________________ 3 D ___________ 4 F _____________ 5 D ___________ []12 3 4 5CH3CHO ԧݨ A B C ߧ

E D F

E

50.2011 20 18-6 ݧ 3:2

[]BD  A 2 3 B ֧ 4 ֧ 6 3:2 C

3:1 D 4 6 3:2 18-14PCT ৳ PCT

1 A D ________ 2 B C

________________C ______________ 3 E F ____________, __________________

4 D ____________ 5 B ________ []1

2 3 4 5

݁ A B C D E F Ҧ 4 2 2

5 1 ֧ 51 (2011 II 30)15
2




H2/Ni


AlCl3


(1 ____________ (2 _______________ CH2 _____________

(3

_________________ _____________ ___________ (4

է

(5)A A ( CH3 CH2R CHR2) A ( )

1 132 (1)9 (2)C10H14 6 (3)



(4)

(5)

52.2011

RR ABCDEF F 278



1



________________ 2A B ___________ ______________ 3B O2 C ___________________CH2OH 4F ________________ 5

C _____________ ݨ ݧ C

OHCCH=CHCHO B HOCH2CH=CHCH2OH A BrCH2CH=CHCH2Br E F 278 D 1 2NaOH 3

. 532011 26

1ޏ` 1:1 11 a 2 է b c d

3 A

A 4 A ()

5 A a c B d b

6

` 1 b

2 NaBrH2SO4 CH3CH2OH


HBrNaHSO4 HBr

CH3CH2BrH2O 3

3 4HBr CH3CH2OH

5d 6 Br2 54(2011 28) 1 2

2 3

ABS 4 ABS (CH2=CHCN) 1 3-

ݧ էݧ ا 1 Br2/FeBr3 Br2/Fe

2135

55 (2011 29) M A

RONa+ RXROR+ NaX

1 2A C 3 4 C D 5 D M 6A (
OH





)

A ݨ էݧا է 1

4CH3OH



6 FeCl3


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