2
7
-
1
48()
749
@
COCO2CO32CS2SCNCNOCNCaC2
G
empirical formulamolecular formula
1. IR
GC-mass
2.
J. Liebig1831
(1)
(2)
(1)
(2) NaOHCaO
NH4NaOH NaNH3H2O
EQ \O(_____________________,Mg(ClO4)2)
Dumas methodCuON2CO2KOHCO2H2OKOH
3.
(1)
eq \o\ac(,1)
a. EQ \F(v1, v2 ) M2 ) EQ \F(, EQ \R(, M1 ))vM
b. EQ \F(V1, V2 ) EQ \F(M2, M1 )VM
eq \o\ac(,2)PMdRTPMdR0.082 atmLmoleKT
eq \o\ac(,3)TKmiTKmi
eq \o\ac(,4)iCMRTiCMR0.082 atmLmoleKT
(2)nn
d
1
mPln
(1) C85.71H14.29(2) 1.75
(1) CH2(2) C4H8
(1) CH85.711214.29112CH2(2) 321.755614C4H8
D
1. caffeineCHNO49.485.1528.8716.49194.2() 48() 36() 24() 12
T
structural formula
1.
CH3COOH
2.
(1)
eq \o\ac(,1) C4N3O2H1X1
C
N
O
X
eq \o\ac(,2)
a.H
(a)CnH2n22n2
(b)
eq \o\ac(,a)XCnH2n2yXyy
1,1
eq \o\ac(,b)OSCnH2 n2Oyy
eq \o\ac(,c)NPCnH2n2yNyyNP
b.H2H2H4H8H
(a) C4H7Cl3 H422103Cl7(b) C4H8O2 H42210108H2(c) C3H7N
H3221997H2
(2)isomer
eq \o\ac(,1)
eq \o\ac(,2) structural isomergeometric isomer
C(C6H8O6)
CC
(1) optical activityLouis Pasteur1844dextrorotatory
isomerlevorotatory isomerracemic eq \o\ac(,)
(2) 1874van't HoffLe Bel, Joseph-Achille eq
\o\ac(,)enantiomerschiral
(3)LDLD
(4)C19.2CL(+)ascorbic acid
(3)
eq \o\ac(,1)
a.
bp118 2bp99.5
b.
7.9 g100 g212.5 g100 g
c.
3.9 D3 D
d.IRIR
eq \o\ac(,2)
a.
b.
c.
eq \o\ac(,3)
d
2
mzn
() CH4ON() C2H7O2N () C4H5 () C8H7Cl () C4H12O
() OHN1HCH5ON() H() 4C10H
D
2. () C6H5NO2() C8H20 () C2H8N2 () C10H18Cl2N4OS () C5H11O2
D
3. 84.() C7H5Cl5() C7H5Cl3 () C7H6Cl6 () C7H6Cl4
d
3
mccn
() () () ()
()()
D
4.
() () () () CH3CH2CH2CH2OH
d
4
mcPwn
16000.7527 190 mmHg() CH3OH () CH3OCH3 () C2H5OH ()
C2H5OC2H5
PMdRT190760M0.751.60.082300M46.125() CH3OH32() CH3OCH346()
C2H5OH46() C2H5OC2H574
D
5. () () () () ()
|
functional group
1.
2.
ROH
C2H5OH
CH3OCH3
HCHO
CH3COCH3
CH3COOH
HCOOCH3
NH2
CH3NH2
CH3CONH2
OH
SO3H
C6H5SO3H
3.
4.
d
5
mxcn
() () HCOOHCH3COOH () CH3COCH3CH3CH2CHO()
()()()()
D
6. () ()() () () 12
D
D
( ) 1.82.()()()()
( ) 2.4.006.001.63H1C12O16()0.18 ()40.9 ()54.5 ()C6H4O
3.A11015052.24
(1)
(2)
(3)
(1) 4(2) 134(3) C5H10O4
*() 4.() C8H11O() C2H4NO2() C4H11() C4H8O2() C3H5N
( ) 5.() C3H6Cl2C4H8O2C4H7Cl2 () C3H4Cl2OC3H8O2C4H8N2()
C2H5OC5H8OC5H11Cl () C3H6Cl2OC4H6N2C4H5Cl3N
( ) 6.ICnI3n1() CnI3n1() CnI3n2 () CnI3n3 () CnI3n4
*() 7.()NH4CNO(NH2)2CO () () 12 () ()
( ) 8.() CH3CH2CH2CH3 () () CH3CH2CH2CH2CH3 ()
( ) 9.() CH3CHCHCH3 () CHClCHCl () CH3(CH2)7CHCH(CH2)7COOH ()
CH2CHCOOH
( )10.31000.93 Kf1.86 m() C2H5NH2 () C2H5OCH3 () C3H7OH ()
C2H5NO2
*()11.80.
()()() ()()1,3,5
( )12.XX2 O2 CO2H2OX95.() H2() CO() CH4() CH3OH() C2H5OH
7
-
2
@
G
1.
2 12 11
2.
C4H9Cl
(1)
(2)
(3)
C3H7Cl
C4H9Cl
C5H11Cl
C3H6Cl2
C4H8Cl2
C3H5Cl3
C3H4Cl4
2
4
8
4
9
5
6
T
haloalkane
1.
(1) 300
F2Cl2Br2I2
(2) X2HX RCHCH2HX RCHXCH3CH2CH2HX CH2XCH3
(3) ROHHX RXH2OROHHXRXH2O
C2H5OHHCl C2H5ClH2O
eq \o\ac(,1) HXHIHBrHCl
2.
(1)
eq \o\ac(,1)
eq \o\ac(,2)
C2H5Cl12 C2H688
(2)
NaOH
NaOH
XOH
HX
HXMOH
eq \o\ac(,1) C2H5Cl(aq)OH(aq) C2H5OHCl(aq)
eq \o\ac(,2)
|
1.
2.
3.
NaOH
chloroform
CHCl3
(1)
(2)
(3)
(1)
(2)
freons1
CCl2F2
(1)
(2)
(1)
(2) 2
CCl4
1.595
teflon
( CF2CF2) n
BHC
benzene hexachloride
C6H6Cl6hexachlorocyclohexane
DDTdichloro-diphenyl-trichloroethane
4,4
(C6H4Cl)2CHCCl3
3
DIOXIN
2
2,3,7,8
PVC
PCBs
H35Cl
1ClFCHClF2CCl2F2CCl3F
2CFCschlorofluorocarbonsODSozone-depleting
substancesCFCsHCFCsCH3BrCCl4O3 O2OClO3 ClOO2ClOO
ClO21989CFCs1996HCFCshydrochlorofluorocarbonsCFCs
31948Paul Hermann MuellerDDT1960environmental
hormone1972DDTDDT20069DDTDDT
d
1
mJcn
C5H11Cl() 5() 6() 7() 8
8
D
1. C3H5Cl()4()5()4()1()2
d
2
mJsn
HBr294.() 2() 2()2() 2() 1
() H3CCHCHCH3HBr () HBr
D
2. 10.10.30.6() 3.5() 2.6() 1.8() 1
d
3
mJPn
()() CH3Cl () () CH3CHBrCH3
()
()()()
D
3. (1)(3)97.
(1) ?() eq \o\ac(,1)() eq \o\ac(,2)() eq \o\ac(,3) () eq
\o\ac(,4) () eq \o\ac(,5)
(2) ? () BHCl () C () EPVC() G() F1,2
(3) ? ()NaOH()NaOH ()NaOH ()NaOH
(1)(2)(3)
D
D
( ) 1.C3H4Cl2() 4() 5() 8() 10
( ) 2. () () () ()
( ) 3.C5H10() 4 () 5 () 6 () 7
( ) 4.()() ()()
( ) 5.CH3CHOHCH3HCl() CH3CHClCH3 () CH3CH2CH2Cl () CH3CHClCH2Cl
() CH3CH2CHCl2
*() 6.(1)(2)(3)
()(1) ()(1) ()(3) ()(1) ()(3)
*() 7.2,2
() 1() 2() 21() 1() 2
*() 8.RX()C2H5BrNaOH(aq)NaBr () CH3Cl ()Teflon ()C6H6Cl6 ()1
*() 9.() ()() ()() () ()()
( )10.21,2() () () ()
( )11.1211CF2ClBr0() CF3Br1301 () C2F4Cl2242 () CF2Br2122 ()
C2Cl2Br22022
7
-
3
@
alcohols
1. HOHCnH2 n1OH
2.
(1) OH
eq \o\ac(,1) OHCH3OH
eq \o\ac(,2) OHCH2OHCH2OH
eq \o\ac(,3) OHCH2OHCHOHCH2OH
(2) OH
eq \o\ac(,1) C2H5OH
eq \o\ac(,2) 31CCCCOH
eq \o\ac(,3) OH
(3) OH
eq \o\ac(,1) 1primary alcohol
eq \o\ac(,2) 2secondary alcohol
eq \o\ac(,3) 3tertiary alcohol
3.
(1)
(2) OH 2 33
d
1
mJn
() 41 () 23 () 22 () 21
() 3
D
1.
() () () ()
4.
(1)
eq \o\ac(,1) CO2 H2 eq \o(\s\up 6(ZnOCr2O3),\s\do 2(),\s\down
6(400 )) CH3OH
eq \o\ac(,2)
a.1CH3CHOH2 C2H5OH
b.2CH3COCH3H2 CH3CHOHCH3
(2)
(3) CH2CH2H2O CH3CH2OH
(4) C6H12O6(aq) eq \o(\s\up 6(),\s\do 2()) 2 C2H5OH2 CO2
(5) C2H5ClNaOH(aq) C2H5OHNaCl
5.
(1)
eq \o\ac(,1) OH22
eq \o\ac(,2)
118 280 76 34.6
eq \o\ac(,3) 123
a.123
b.3123
c.3123
C4H10O
mp
bp
g100 g
11
90
118
7.9
22
114
99.5
12.5
223
25.5
83
(2)
eq \o\ac(,1)
C2H5OHK C2H5OK12 H2
eq \o\ac(,2) ROHHX RXHOH
C2H5OHHBr C2H5BrH2O
eq \o\ac(,3) H2SO4Al2O3
180
130
C2H5OH eq \o(\s\up 6(H2SO4),\s\do 2()) C2H4
(CH3)3COH + HOCH3 eq \o(\s\up 6(H2SO4),\s\do 2())
(CH3)3COCH3
eq \o\ac(,4)
a.
3 CH3CH2CH2OH1Cr2O728 H 3 CH3CH2CHO2 Cr37 H2O
5 CH3CH2CH2OH4 MnO412 H 5 CH3CH2COOH4 Mn211 H2O
CH3CH2OH12 O2 eq \o(\s\up 6(Cu),\s\do 2()) CH3CHOH2O
b.
5 CH3CHOHCH32 MnO46 H 5 CH3COCH32 Mn28 H2O2 2244
eq \o\ac(,5) 3OHH
6.
CH3OH
64.7
C2H5OH
2500
(1) 78.3
(2) 95
(3) 99.5
(1)
(2)
CH2OHCH2OH
EGethylene glycol
(1) 197.3
(2)
(1)
(2)
OH30
CH2OHCH2OHCH2OH
glycerin
259.0
(1)
(2)
(3)
OH
d
2
mJsn
()KMnO4() CH3CH2BrKOH(aq)()()()()()
() eq \o(\s\up 6(),\s\do 2()) ()
D
2. ()() COZnOCr2O3 ()() ()
d
3
mJn
()OH()OH () () 3 () 3 ()
()() 3() 123
D
3. () 1() 2() 22()bp ()mp ()()KMnO4(aq)
d
4
mJn
10.8() 1() 2 () 21 () 22 ()
n1n0.85n41()()()
D
4. CH3OH HCHO()HCHO HCOOH ()CH3OH HCOOH()()()()93.()
()()()()2()()2()()4
d
5
m`Jn
() () () () 3 ()
()()()
D
5. ()() ()()1 ()100
G
phenols
1. OHArOHAraromatic
3
2. OH1
2,4,6
3.
(1)
(2) NaOH
4.
(1)
eq \o\ac(,1) 41 182
eq \o\ac(,2) 25 8 g100 g
(2)
eq \o\ac(,1)
eq \o\ac(,2) Ka1.281010Ka1=4.3107NaOHNa2CO3NaHCO31CO22NaHCO3
1NaOH H2O eq \o(\s\up 6(CO2),\s\do 2(),\s\down 6((H2CO3)))
NaHCO32
eq \o\ac(,3) OHOH
eq \o(\s\up 6(Br2(aq)),\s\do 2())H2O
eq \o\ac(,4) NaKCaBaNa 12 H2
eq \o\ac(,5) FeCl3
6 2 FeCl3 Fe3
5.
(1)
(2)
d
6
msPn
82.()()()()
()()
D
6. pH () ()()Na()FeCl3()
T
ethers
1. OROR' RR'
MTBE
2. O
3.
(1) 2 H3CCH2OH eq \o(\s\up 6(H2SO4),\s\do 2(),\s\down 6(140
))
(2) C2H5ClCH3ONa C2H5OCH3NaCl
4.
(1)
eq \o\ac(,1) 25 78
eq \o\ac(,2)
(2)
5. CnH2n2O
(1)
eq \o\ac(,1)
eq \o\ac(,2)
(2)
eq \o\ac(,1) O
eq \o\ac(,2)
C5H12O
a.81(42(33(1
b.6
(3)
6.
(1) 34.6
(2)
(3)
d
7
mn
82.()()()C2H6O()()
()56()C4H10O()
D
7. b.p. 34.7 () 1()()()
d
8
mJPcn
C4H10O ()6 ()2 ()2()2 ()1
()7() 1(2(3()3() 21
D
8. C4H10O80.(1) (2) 5 mL1.0 10 (3) 3 mL0.5 1 M3 mL85 1 mL (4)
IUPAC
(1) CH3CH2CH2CH2OHCH3CH2CH(OH)CH3CH3CH(CH3)CH2OH CH3C(CH3)2OH(2)
CH3CH2CH2CH2OHCH3CH2CH(OH)CH3CH3CH(CH3)CH2OH(3) (4) 2
7.
RCOOH
ArOH
ROH
ROR'
Na
NaOH(aq)
NaHCO3(aq)
CO2
Na2CO3(aq)
CO2
CO2
d
9
mJPOn
2222XYXYY(1) (2) (3) Y(4) 88.
(1) CH3CHCHCH2CH3Br2 CH3CHBrCHBrCH2CH3(2) CH3COCH2CH3(3)
CH3CH2CH2CHO2 [Ag(NH3)2]3 OH CH3CH2CH2COO2 Ag4 NH32 H2O(4)
(CH3)2C(ONa)CH2CH3H2
()2()22()()()2
D
9. 82.()()()()()()
D
10. ()NaOH(aq)() ()()NaHCO3(aq)()FeCl3(aq)
D
D
( ) 1.C4H8OBr2CCl4 () CH2CHCHOHCH3() CH3CH2COCH3()
CH2CHCH2CH2OH() CH3CH2CH2CHO
*() 2.
() () ()FeCl3 ()NaHCO3CO2 ()2,4,6
( ) 3. () () ()130140 ()
( ) 4. ()1 () 11 () ()
( ) 5. () 0.8 () 1.0 () 4.0 () 5.0
*() 6.C4H10OC4H8O ()3()3()4()2()3
7. eq \o\ac(,1) eq \o\ac(________,)170 eq \o\ac(,2)
eq \o\ac(,5) eq \o\ac(________,)eq \o\ac(,1)
eq \o\ac(,3) eq \o\ac(________,)
8.11. 92.
( ) 8.()()()()
( ) 9.()()()()
( )10.5000 ppm1 ppm1060.60.78 gmL() 1() 3() 5() 6
( )11.()()()()
( )12.300() () () ()
( )13.83.() CH3CH(OH)CH2CH3 () CH3CH2CH2CH2OH()
CH3CH(CH3)CH2OH() CH3CH2CH(OH)CH2CH3() (CH3)3COH
*()14.4.5STP1.12
83.() HOCH2CH2CH2CH2OH() CH3CH(OH)CH(OH)CH3() CH3OCH2CH2OCH3 ()
CH3OCH2CH2CH2OH() (CH3)2C(OH)CH2OH
( )15.86.() K2Cr2O7 () Mn(NO3)2() CuSO4() AgNO3
( )16.2 89.() () () ()
( )17.C8H10O() () () () 91.
( )18.91.()()()()
19.C4H10OAB93.
(1)
(2) ACH3(CO)CH2CH3
(3) B
(1) 22(2) 2(3) 1 21B1 2
7
-
4
@
aldehydesketones
1. carbonyl eq \o\ac(_______,CnH2nO)
2.
(1) RCHO
(2) RCOR'
3.
(1)
(2)
4.
(1)122 C2H5OHO2 eq \o(\s\up 6(Cu),\s\do 0(),\s\down 6(250 )) 2
CH3CHO2 H2O3 Cr2O728 H 3 RCOR'2 Cr37 H2O
(2)
(3)2
5.
C1
C2
C3
C4
C5
C6
RCHO
1
1
1
2
4
8
RCOR'
0
0
1
1
3
6
C5H10O(1) (2)
G
1.
(1)
(2)
(3)CO
C2H5COOH140.7 C4H9OH117 C2H5COCH379.6 C3H7CHO75 C5H1236
(4)
2.
(1)HCOH
eq \o\ac(,1)
Cr2O728 H 3 2 Cr34 H2O
eq \o\ac(,2)
a.Fehlings reagent
(a) Cu2OH
Cu2Cu(OH)2
(b)Cu2 eq \o\ac(__________________,Cu2O)
b.Tollen's reagent
(a)Ag2O[Ag(NH3)2](aq) eq
\o\ac(___________________,[Ag(NH3)2](aq)OH)
(b)silver-mirror reaction
(2) H21 H22
d
1
mBsn
()1()()()1()2
() 1 ()()()
d
2
mBcn
C4H8O93.
D
1. 1 mol11.2H2
() CH3CHO() CH3CH2CHO () () CH3CH2COCH3()
d
3
mBn
97.()() 2()()3()
()2()()
D
2. AB()()() ()BA ()
D
3. ()()()()
T
HCHOformalin
1.
2. b.p.21 m.p.92
3. sp2
1. 37
2.
CH3CHO
1. K2Cr2O7
2. b.p.20
1.
2.
CH3COCH3
1. 2
2. 56.3
3.
1.
2.
d
4
m`Bn
()()()()()
()()
D
4. 82.()()()()()
D
5. ()()sp3 ()()CuO
D
D
( ) 1.21530 eq \o\ac(,4)() eq \o\ac(,1) eq \o\ac(,2)() eq
\o\ac(,1) eq \o\ac(,3)() eq \o\ac(,3) eq \o\ac(,4)() eq \o\ac(,2)
eq \o\ac(,4)
( ) 2.()() () eq \o\ac(,3) eq \o\ac(,1)() eq \o\ac(,4)
*() 3.C4H8O
()3()3 ()1()1 ()Cu2OH2
( ) 4.C4H8O() CH2CHCH2CH2OH() CH2CHCH(OH)CH3() CH3CH2CH2CHO()
CH3CH2COCH3
( ) 5.() 23() 22() 21() 33
( ) 6.()()()()
( ) 7.() 2()()()
( ) 8.CH2CHCHO()1()()KMnO4()
( ) 9.2() CH3CH2CH2OCH3() CH3CH2COOCH3() CH3CH2COCH3()
CH3CH2CH2CHO
*()10.0.53 mL1
3 mL2 NH2SO48590 3 mL() B () B () B () B()CH3CH2COOH
( )11.(CH3)2CCH(CH2)2C(CH3)CHCHO() ()C10H20O ()()
12.A5488.911.1()B()A2C()A1D()EE81.
(1) A
(2) ABCDE
(1) CH88.91211.112354C4H6(2)
ACH3CH2CCHBCH3CH2CCAgCCH3CH2CBr2CBr2H DCH3CH2CCHECH3CH2COCH3
5. 5 CH3OH4 MnO412 H 5 HCOOH4 Mn211 H2O
3.()()
2.()()NaHCO3NaOH
*
10.()()()()()
7.()
9.()()
1.1 mol0.5H2()()22.4
4.()
8.(1)(2)1(2((3)2(
C2H6O
C3H8O
C4H10O
C5H12O
1(
2(
3(
1(
2(
3(
1(
2(
3(
1(
2(
3(
1
0
0
1
1
0
2
1
1
4
3
1
1
2
4
8
1
1
3
6
6.()()
3.()()()()()()()()()()()()() 3(
17. eq \o\ac(,1) eq \o\ac(,2)2()()4
2.()()
11.()C10H22O
2.()A()AB
*
8.() CHCl3() ()1
2. eq \o\ac(,1) eq \o\ac(,2) eq \o\ac(,3) eq \o\ac(,4)1() eq
\o\ac(,1)
4.1()
1.()2()1
10.
7.()()() () ()
8.()
5.
9. 2CuOCuO2
1.(1)7(2) 310
*
6.C6H615
3. C4H8O21()()2()()2
3.(1)(3)BCl2CCHClCHClEG eq \o\ac(,1) eq \o\ac(,2) eq \o\ac(,3)
eq \o\ac(,4) eq \o\ac(,5)NaOHNaOH
1.41()()
6.()MnO4
10.()
7.() NH4CNO(NH2)2CON2H4CO()()()()CH2
4.() C8H11OH() C2H4NO2H() C4H11H
3.(1) A152.2447.76A110O EQ \F(11047.76,16) 3.2835A150O EQ
\F(15047.76,16) = 4.4775O3.28354.47754(2) A EQ \F(164, 47.76%)
134(3) ACH13452.2470CH5C10HAC5H10O4
*
6.()C2H6OC2H4O() 12OH
1.
CHNO49.48125.15128.871416.49164521C4H5N2O485281697194C8H10N4O2
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