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5.4
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5.5
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5.6
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5.7
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5.8
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5.1
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5.2
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5.3
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2 !.)0/01 #1$.202.0.2
+
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0&20!2 #12/.
. 2110!.02!).
0202!).
02!).
/ 2+02!).. .02
2 2 #C .)2 . 12.2
5.
.22!..2 12& !.+.2/!10&

&+ &+ &O
_
+ AgOH &+ &+ 2+ + AgCl .

_
&+
&+
&+ &+ 0J&O 2

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CH3-CH2-CH3 + Mg(OH)Cl
&+
2. !.0/01. #1$.2 2.0..212 $.2.

+
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6. )2" !."0+10" CH3-CC-CH3 (I), CH3-CH2-CCH (II),

CH3-CH2-OH (III) .CH3-CH2-ONa (IV)
i) 03. #)0"/)220"
. ) II)

(I).(IV)

/
(II) . (III)
. (III)

(I) .(IV)
(IV)
/
(III) .(IV).
(I) .(II)
ii) 03. #.1"/)220"
7. )2" !."0+10"CH3-COOH, C6H5-OH, C3H7-OH .CH3-CCH

.2/! *0NaHCO3:
. CH3-COOH . C6H5-OH
) CH3-COOH
CH3-COOH, C6H5-OH .C3H7-OH
/ )0"
10
8. ) 2" !." 0+10" C6H5COOH, C6H5OH, C6H5-CH2-OH .

CH3-CCH
i) .2/! *0
. )0"
) C6H5COOH.CH3-CCH
) C6H5COOH , C6H5OH . C6H5-CH2-OH
/ ) C6H5COOH
ii) .2/! *0NaOH:
. )0"
) C6H5COOH
C6H5COOH . C6H5OH
/ C6H5COOH , C6H5OH . C6H5-CH2-OH.
9. ) 2 1* 2& !.+ 0+10& HCOOH, CH3CH3, CH3CH2NH2 .
CH3COONa
i) .2/! *02 HCl:
. .
/*
2!0"
/ )0"
ii) .2/! *2)1 02 HCl )1 .02 C3COOH:
. .
/*
2!0"
/ )0"
10. )2" !."0+10"CH3-CH=CH2 (I), CH3CH(OH)CH3 (II),
CH3-CCH (III), CH3CH2CH2NH2 (IV) .CH3-CC-CH3 (V):
i) .2/! *0.&.)/#.2! *.!*! #
. (III)
(II).(III)
(IV)
/ (III). (V)
0 (I).(III)
ii) 03. #)0"/)220"
. (III).(V)
(IV)
(II).(III)
/ (I)
iii) 03. #.1"/)220"
. (IV).(V)
(II)
(II).(III)
/. (IV).
11. ) 2 " 2& 1#2.2 1 0!+ 0+10& 0 !.) 2* C5H8,
.2/! *0.. )/#.CuCl .1$.2 #0!.!#! .
. .
/*
2!0"
/ )0"
11
12. 2".2/!10" 0"!..2 *2.02 $.1)#!)3"

# .212.1"
i) 2 #!)3 .2/!.12! 0.)
. .)0/01).1*0#2 0* "02! &
.2)0/01).1*0#2 0* "02! &

#/20! )! 0/01).1*0#2 0* "02! &
/ .) #/20! )! 0/01).1*0#2 0* "02! &

ii) . $&! *1. /.0.
. .)0/01).1*0#2 0* "02! &
.2)0/01).1*0#2 0* "02! &

#/20! )! 0/01).1*0#2 0* "02! &
/ .) #/20! )! 0/01).1*0#2 0* "02! &

13. ) 2" !." 0+10" CH3COONa (I), CH3CCNa(II), CH3ONa (III)
.NaCN (IV)
i) .2/! *0.#. /.
. ) II.IV)
) II), (III.IV)
) I.III)
/ )0"
ii) / # .2/!.1 . /)1" 2" .!." .#1/." .2 2 .2/!.12 #"0.# $&!/
.
II.IV)

I.III)
/ )0"
II), (III.IV)
_
14. )2..2/!.12!.: 2 + (I), & + (II),
_
&
N (III),
$.!.2! 2.&"#!)3.2.
. (I). (II)
(II) . (III)
(II). (IV)
/ (I), (III).(IV).
12
1+
(IV)
15. )2"/* $".2/!10"

CH3OH + SOCl2 CH3Cl + SO2 + HCl
(I)
CH3OH + Na CH3ONa + /2H2
(II)
$.!.2! 2.&"#!)3# .212.1

. (I)
(II)

(I) .(II)
/ ..
16. 0 2 0/!.1 #/.2 * /.*.2 " 0/ # 2 # .!*! # 12 .#
$&!/ .!02. !.&1 .22.2/!.12"&1"
00 # $&!/ ! *20
. 0..# $&!/&
.# $&!/ 1 0!"2 #
2 .# $&!/
/ ..! .2)..)$&! #
17.
.220/!.1Cl2 10 #2 12 /$#2 3&".!02.

. ) ..# $&!/
0./* 1 0!+.# $&!/&
).2.1 0!0 !.)2* C4H9Cl
/ 0.$&! .!.+&2 # #2. #
18. .2 #. *.2 #/ */01 *02.*/* .2)&C0..2-
12 $.10 10m .10 10m.

"2 #/01 *02.*/* 02 +.2)&C 12 )! 2 #0 #
0.
-
. 1,5410 10m
-
1,3910 10m
-
1,3410 10m
-
/ 2,8810 10m
-
0 1,5410 10m10 10m.
13
19. )2 #"#/! .0"C6H6, C2H4, C4H6 .C6H5-CH=CH2

i) . $!&.2 #/#.!& #10CCl4:
. ) C2H4 .C6H5-CH=CH2
) C6H6, C2H4, .C6H5-CH=CH2
) C2H4, C4H6.C6H5-CH=CH2
/ )
ii) 0!$012 )!)2 #1/01 *"
. C6H6
20.
C2H4
C4H6
/ C6H5-CH=CH2.
.22! 1$&! #10! .!02.

. /$&! !
/$&! !
$&! !
/ 0.$&! .!.+&2 #! . #
21. *! ! ')2"! 1"HBr 12 #2 0.2

. #2# !&/
1 #2# !&/
/0#20! 2." #2# !&/
/ 2!2 2." #2# !&/
22. )2".!.2&$"01+10"
+ 62 +J62
CH3COCH3
CHC-CH3 + H2O
(I)
CHC-CH3 + 2HBr %U&+ &+ &+
(II)
_
%U
&O
_
CHC-CH3 + 2Cl2 &O&+ & &+

_
_
(III)
&O &O
3G3W1L
CH3CH2CH3
CHC-CH3 + 2H2
(IV)
0...1
. (I)
(II)
(III)
14
/ (IV).
23.
.2 2 .2/!.1 ." &1" 0 CH3CH2MgCl . #/!)#1 2 #

! ')2 "! *200# #2.))2..!.&/0/ .
! *20)2&10.
24.
. CH3CH2CH=O
CH3COCH3
CH3CH=O
/ CH3CH(OH)CH3.
.220/!.10)".2/!.12! #Grignard10...#/!)#12 #! ')2 "! 1"! *20

. !&2 2.". )
/0#20! 2.". )
2!2 2.". )
/ !&2 2." /0#20! 2." 2!2 2." . ) . . 0 2 0/ "
2 #.2/!.12! #Grignard #$!1 0
25. 0.)0./#.2)..!.10#.100! 112.2

.! #&1
. #/! ) #
0! *
.2/!.12! #Grignard
/ #/! ) #.2/!.12! #Grignard.
26. 0.2.#2#/! )&102)"0./#.2).! *%0. )

. CH3CH2OH
CH3OH
&+
_
&+ &+ &+ / &+ & &+

_
2+
27. !+2 12/ 2 #$.1 *2".2/!.1"
CH2=CH2 + HCl CH3-CH2-Cl 0.
. #21$1HCl H + Cl
+
020! #21$1HCl H + Cl

! 1CH2=CH2 + HCl &+ &+ + Cl
/ 02.2! 2 #CH2=CH212!. &+ &+ .
15
_
2+
28. 12.0!)20! .) 2. 0/01. .! .2)2. # 1$.2 2. .2
2".2/!10"! 1"HCl 10. ! .0# ! 0.2

. &+ &+
&+ &+ &+

/ &+ &+ &+

_
&+ &+&+

0 &+ &&+
&+
_
&+
29. 012$.2/!.1C4H8O + H2 C4H9OH 0./#.2).

.!.10#.1 *
. .) . )
)0" #2.)0"
) !&2 2.0" #2.)0"
/
!&2 2.0". /0#20! 2.0". )0"0 !.)2* C4H10
30. 00/!.1.. */.*.2 " 10$&! #2 .!02.

. #2
#2
0.)&2&/#.2+.0&0 !.)2* C4H8
/ 0. #20&00#0..!..#1/.
31. ) 2 0/&1 2" ..)" 0 ) /#. K2Cr2O7 12 1#
0! !.1..02.
. ) ..
....) *0..#2+
) ..) *
/ 0..! #+0+10&
32. )2 0/&12&!&2 2.+. +0) /#.KMnO4 12
1#0! !.1.. 2.
. ) .! # .
./0/0" .
) ./0/0"
/ ).2..!.&
16
33. 0! 10! *12 !.&1.! #1.H2SO4- HgSO4.!02. !.&1 #.02 .2/!.12! Fehling. )2.
/0/ ..#2! *20)2&10.
34.
. . / 20.
2 !
2 .
/ ..
.22.2/!.12"&1"0..)/#.&/ #.! 2.

-
2! ..2 )CH3CH(CH3)COO .

)2"0+10"
CH3CH(CH3)CH2CH(OH)CH3
(I)
CH3CH(CH3)COCH3
(III)
CH3CH(CH3)CH(OH)CH3
(II)
CH3CH(CH3)CH(Cl)CH3 (IV)
&10./#.2).0.
35.
. IIII)
III) III)
IIIII)
/ IIIII) IV).
.2202.2! 2 #0 #10.2 0) 02.2!02..!$! "2! 0) 12/ I) .121#$0.2 2! 0) 02.2!02.! ".12/ II).
i) +.2"02.2! " #!..2 *2..22./* .!.&12/.I .$!1 *2..212 $.2..2/!.12!.
. #)32.! #1.02. *.2.*2
0.# *3.H2SO4/#.3

*2!&1" - 2.! #1.02. *.2.*2
/ 2/#.3
ii) $" .2/!10" # !..2 *2. .2 2. /* .!.&
12/.I.II 0..212 $.
. 0 #/02!&1! 1
0 #/02!&1..&
# .212.1! 1
/ # .212.1..&
17
36. )2 "2&1#2.21 0!+.! #+0+10&0 !.)

2* C4H8O
i) . #2 .2/!.12! Tollens:
. .
2!0"
/*
/ )0"
ii) .2/! *0..)/#.&/ #.1$.2 #2! .
. .
2!0"
/*
/ )0"
37. )2" !."0+10"CH3-CH2-OH (I), CH3-CH(OH)-CH3 (II),
CH3-CH2-CH=O (III) .CH3-CO-CH3 (IV)
i) . $!&.2 #2 1 0H2SO4/#.KMnO4:
. )0"
(I), (II).(III)
) I) .(II)
/ ) III)
ii) . #2 .2/!.12! Fehling:
. ) III)
(III) . (IV)
I) .(III)
/ )0"
iii) / #2&/ 3 !.2/!.1
.. ) (IV)
(I), (II).(IV)
,,.,9
/ (I), (III).,9
0$ .20*#1
38. +...2.12 *!+1.. 0#122.0.)./. #$ #.# *22..20! 2.0
. /#.1" )200 #/020!+ 2.2.00*0!. .
0!) )20. .!* 2.2.#/.2 /.#2 .
NaOH Na2CO3 .121#$0.. .!* 2.2..2. #1$.2 2.
/ CH3CH2OH .121#$0.. .!* 2. 012!0" #1$.2 2.
18
39. 2! #0!.!.10#02.00/!.1#)0! !.1.C:

. 0.2 "3H2SO4 10! . 2!)
2! #10#0!
310#0!
/ 0.2 "3H2SO4 10! . /)
40. .2!#0!/.0.2!012!0"2"#0!"0
. !01. .
#.)!012. .
.)!012. .
/ .! .
41. 2. . #0!/. . 2. 2!. #/! *. 2" #0!" 0. 0120!
.0
. !01. .! * !. *! #"
2 / !01 *
2 / .!) *
/ 2 / .)!012 *
42. 01.& 10)"2 *2!#0!/ #.!02.0.#0!"
.
. .!+ &
.2& !01& &
.2&.!+ &
/ !01&..)!012& &
43. . !!#.2/!12&1. #+ 3002.12 )2.#2

. /0# * #2#/!)#12&+.2&0.&
/.* 2.12..12...
02 #! *&"3#!.02.3 !"2 #.! *!* #12 0!)
-
/ 0!$ #12 )!)2 #"2)3 /.RCOO .

44. )! 0)"1. # *. 2002..)
. .#/!)3#/! .!..#1/...)3 2)!
.)3#/! .!..#1/...#/!)3 2)!
-
#/!)3..2)2.Na .)3..)2.RCOO
/ .)3 .* R-) ..#/!)3 2)! COO Na ).
19
45. 2 )! 2&1#02+. !!#.2+

i) 2 #/!)3 2.0.
. 2 2)! SO3
#/! .!..#1/.R

.!&.2)"/.2* "
/ 2 .* R-.
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#/! .!..#1/.R

.!&.2)"/.2* "
/ 2 .* R-.
46. 0!2) 2!2! 2 #) .!.10#02. 0 0/!.1 12
2 #)
. 3
2
0.2 "3H2SO4
/ 0.2 "2H2SO4.
47. +...!.10#1 #0.1#02). !!#.2).!0./.2 #0

. 0) H2SO4.NaOH
.# 0) H2SO4.NaOH
.# 0) 0.3H2SO4.NaOH
/ .!) *..#12)2!
48. 02.2! 2&0.&10!..2 02.12 $..0
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20
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1$1/01 *.+".02 $.!.2!1)2"1$1".#2"12III).
2.
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(II)
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. ! # .)
.. CH3Cl
. 0# .2)
. CH3CH3
1. 020! #2
+. .#)!.
. CH3CH(Br)CH3
2.
. 1 ! # .2)
/. CH3CH2CH2MgCl
#2
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02.1212III.01$02.212 $1
(I)
(II)
(III)
. !
.. Na
1. CH3CH2NH3+Cl
. ..) *
. NaOH
2. CH3CH2CH3
+. .#.
. NaHCO3
3. CH3COO Na+
. ! # .1 $&!/
/. HCl
4. CH3CC Na+
. 3.)
0. H2O
5. C6H5O Na+
3. 212 $120 .3 1.2. 2 0 !. &1 2" 12" I)
0..)2..2/!.12!.2"12"II02 .#2.2/!
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(II)
. ! .)2!
.. .&.)/#.CuCl
. 0 ') *
. ..) *
+. .#.
. NaOH
. !
/. HCl
. ..)
0. Na2CO3
. 3.)
. a
21
4.
.22# .212.12 #. ) #2&.#. /&0...)2.#!)3..2/!.12!.2"12"I.! 2. !."0+10" #. #12"20" #0!. 2.1212II)..02021$02.212 $1
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. H-O:
.. .!."
. 012!.".! # * "
. H3N:
+. NC:
. .
. & O:
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. -CC:
0. 2!
. .".#.& #
. -COO:
5.
0 !.&12"12"I.2/!0..2/!.12! 2"12" II . ! *20 . .) 2" !." 0+10" 2" 12" III .
02021$02.212 $1
(I)
(II)
(III)
. CH3CH2CH(OH)CH3
.. #/.2)/#.Ag2O
1. ..) *
. CH3CH(Cl)CH3
. CH3OH
2. /0#20! 2."
#2# $&!/
3. ! .)
+. CH3CONH2
. SOCl2
. HCOOH
/. #/.2)/#.H2SO4 4. 0.)"
0#012!."
22
6. ..212 $1020.0..)2" !."0+10"2"12"I0)1.

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2".2/!.1" #0!.02.1212III).
(I)
(II)
(III)
. 0)
.. Br2 /.# 10CCl4
1. C6H5Br
. .
. Br2 .! #1./$#2 #3&2)"
2. C2H5Br
+. .
. Br2.! #1.FeCl3
3. C6H5NO2
/. 3.H2SO4
4. C2H4Br2
0. HBr
7.
.22.2/!.1.0".)2" !."0+10"2" 12" I 0

.)2..2/!.12!.2"12"II.!02.. !.&1
#0!.02.1212III.0202"1$02".212 $10"
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8.
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. CH3CH=CH2 .. /#.Br2 10CCl4
1. 1,2-/!& .
. CH3CCH
. #/.2)/.H2SO4
2. /!& .
+. CH2=CH2
. #/.2)/.H2SO4 - HgSO4 3. ! .)
. CHCH
/. HBr
4. ! .)
.22.2/!.1.0)".)2..2/!.12!.Grignard 2"12"I)
0..)2".! #"0+10"2"12"II! *20 !.&102#/!)#12" .".!02...)2". )0" #0!.02.1212III.0202"1$02".212 $10"
(I)
(II)
(III)
. CH3CH2MgCl
.. HCH=O
1. 20# #2.)
. CH3MgCl
. CH3CH=O
2. #2.)
+. CH3CH(CH3)MgCl
. CH3COCH3
3. #2.)
. CH3CH2CH2MgCl
/. CH3CH2CH=O
4. 0# #2.)
23
9.
.22.2/!.1.0".)2" !."0+10"2" 12" I 0

. .) 2. .2/!.12!. 2" 12" II .!02. !. &1 #
0!.02.1212III.0202"1$02".212 $10"
(I)
(II)
(III)
. CH3CH2CN .. #/.2)/.H2SO4
1. .#.
. CH3CH=O
. NaCN / H2SO4
2. ! .)
+. CH3CN
. H2 .! #1.i
3. ! .) *
4. #/! #! . 2!
. CH3COCH3
10.
.22.2/!.1.0".)2" !."0+10"2" 12" I 0

. .) 2. .2/!.12!. 2" 12" II .!02. !. &1 #
0!.02.1212III.02021$02.212 $1
(I)
. CH3CH2OH
(II)
(III)
.. .2/!.12! Fehling
-
1. CH3COONa
. CH3COCH3
. MnO4 /H
2. CH3CH2COOH
+. CH3CH2CH2OH
. J2/NaOH
3. CH3COOH4
. CH3CH=O
/. Cr2O72 /H+
4. CH3CH=O
11. 2 12 II $.!.2!02. 2 0/ " 2" .2/!.1" 0 1 2 .
02.2!02.0&12"12"I10..)2"0+10"2"12"
(III.0202"1$02".212 $10"
(I)
(II)
(III)
. #2.
.. 0/&1
1. . 0)
. #2.)
. ..&
2. PVC
+. # $&!/
. .)1.1
3. #2.) *
. #2.)
/. #0!1)"
4. #2
. 2! 0)
0. . 3 !.2/!.1
5. &/ 3)!
24
12. ..212 $10200..)2" !."0+10"2"12"II02"

0+10"2"12"I.)2" 0".#2 !0.! *%00.)
.2/!.1 .+" . 0 . .) 2 #" $.!.2!1 *" # 0!.
2.1212III).
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. .# $&!/
.. CH3CH2OH
1. #!)3# .212.1
. ..
. CH3COOH
2. ..&
+. .
. CH3CH=O
3. 02! )3! 1
. .
/. CH2=CH2
4.
0. CH3CH(OH)CN
5. .)1.1
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6. #!)3! 1
13.
0 02.2! # 0!!302. 12 12 I !..2 02. 0 .

) .2/!.1 . .212 $1020 .3 1.2. .0. .) 2" 02.2! "2"12"I02 .2/!.12! 2"12"II02 .#2!..2 02.
(I)
(II)
. CH3CH2Cl CH3CH2CN
.. SOCl2
. CH3CCH CH3CCAg
. HNO3 - H2SO4
+. CH3CH2OH CH3CH2Cl
. #/.2)/#.H2SO4
. CH3CONH2 CH3COOH
/. .2/!.12! Fehling
. C6H6 C6H5NO2
0. 0.NaCN - H2SO4
. CH3CH=O CH3CH(OH)CN
. .. )/#.
. CH3CH(Br)CH3 CH3CH=CH2
. NaCN
,. CH3CH2CH2OH CH3CH2COOH
. .&.)/#.AgNO3
. CH3CH2CH=O CH3CH2COOH
. ) 0H2SO4/.KMnO4
25
14.
.0. .) 2" 02.2! " # 0!!3 2. 12 12 I !..2 02.0.) $.2/!.1..212 $1020.0..)2"
02.2! "2"12"I0..)2 #"$.!.2!1 *"2".2/!.1"
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. 0) 102! 0)
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. ! .)10! .)
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. ! 1
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/.
. ! .)10! .) *
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0 2 $.!.2!1) .#2" 2" .2/!.1" # 0!.02. 12 12
(III).
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. CH3CH(OH)CH3 .. ..)/#.J2
1. . 3 !
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. .&.)/#.AgNO3
2.
+. CH3CH2CH=O
. #/.2)/#.H2SO4
3. # .212.1
. CH3CH=CH2
/. ) 0H2SO4/.K2Cr2O7 4. ! 1

0. /#.Br2 10CCl4
26
5.3. !&210"1#!&1"
1.
.2 2 !..2 1 2& !.+ .2/!10& 1$.2 2. !.0/01.1.2)20!..)2. .0.2.2.
. 1$.21)"2 #" 3002.121$10)"/01 *C-A2!) "2"1$1" 0.!22. #!&" .) 2 /.3 ! ......... 02.*
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2. !. 0/01. # 1$.2 2. 0.
. 1$1 02.
0+ 12 .202 0!2&1 2. !. 0/01. # 1$.2 2.
0..1$1 02.
2.
.2 2 1$1 2& /01+ C-Cl , C-MgCl . C-H 12" 0+10"
CH3CH(Cl)CH3, CH3CH2CH2MgCl . CH3CH3 1$.2 2. .212 $.
2. !. 0/01. .
2. . 2. .212 $.
.
3. !."0+10"CH3COOH, CH3CH2OH, C6H5OH .CH3CCH 03. #. /)22. #0.

)2"0+10".#2".2/! *
.0Na .........................................
0NaOH ....................................
0NaHCO3 .................................
4. !." 0+10" CH3CH2MgCl, CHCNa . CH3CH(CH3)ONa .2/! * 0 2 0!) . 1$.2 # .212 $. 2" !." 0+10"
.
2".2/!10".#2"&"1$#!"10"1#0!3! 2..212 $.2.)2. .. . 2. .
2. .
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27
5. !." 0+10" 0 0) 2* R-NH2 2.

.03. #.../)220"21.2/! *0
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.2/!0.1$.202.2 ."
6. ..! #.)2.$ #/)220"21.2/! *
0 1$#! . . 1$.2 # 2. $ 2
-
CH3COO )2..2/!01$.202.2 *

7.
.2 2 .2/!.1 CH3CH(Cl)CH3 0 CH3COONa 2 #!)3 .2/!.12! 0+02.02 2."2 C 2 #
CH3CH(Cl)CH3.. 12..)0. 201...!02.

!.
&1

#
02.
................................................... .
8.
.2 2 .2/!.1 CH3CH(Cl)CH3 0 NaCN 2 #!)3 .2/!.

12! 0+02. 0 2 2." 2 C 2 # CH3CH(Cl)CH3
.. 12..)0. 201...!02. !.
&1 # 02.
.2/!.1 .#2 $.!.2!02. &" .2/!.1 . /)1" /)2
..................................................................................................................... .
9. 2" .2/!10" 12" 0" . )0" ROH) 03. # ) $.!.
2!.1$02. /01)"$.22.2/!.12"CH3CH2OH
0Na 1$.202. !.&1202.12".2/!10"# .212.1"1$02. /01)"$.22.2/!.1 2" CH3CH(OH)CH3 0 .!02. !. &1
.2..!..2. .. .!* 2..)2 1*12.0. 201..2/!.1.02.2 02.! "2.
........................... .
28
10.
.2 2 .2/!.1 CH3COOH 0 CH3CH(OH)CH3 /.

2 #CH3COOH.2.12.2..)2#!)3 /.
2"CH3CH(OH)CH3..!02. !.&1
# 02. .2/!.1.#2 # 02. !..2 02. .! #1.
0. .3/! . .202" 3 !" .2/!.1 02.
......................................... .
11. . 1#!+1020 2. 0 12 .!.2& .. .3 * 020 #)% )2
10010!&12"!+2"12".2/!02 .2/!.12! 2"
/0*20!"12"..!02. !.&12"2!2"12"
!.&1
2/!.12!
!.)! ')
CH3CH2OH
......................
CH3CH2Cl
CH3CCH
..................
CH3CCAg
.....................
CH3Cl
.....................
C4H6
.. )/-
......................
#.CuCl
.....................
CH3CH2Cl
CH3CH2OCH3
12. .1#!+10202".!.2&$"01+10"
+ 2

. CH3CH2Cl + ......................
........................ + AgCl
CH3CH2Cl + ...................... CH3CH2CN + ..................

CH3CH2Cl + ...................... CH3CH2CCCH2CH3 + ..................
/ ................... + ...................... CH3CH2COOCH2CH3 + .................
0 ................... + CH3Cl CH3OCH2CH3 + .................
29
13. .1#!+10202".!.2&$"01+10"..!%0202. ).2.)&2& !.+0+10& #1#02$ #1.#2"

+
. ........................ + ............... H
CH3COOH + CH3CH(OH)CH3
CH3CH2CONH2 + ............. + H ........................... + NH4
+
C6H6 + ................. FeCl3
......................... + HCl
/ .................... + ................... H2SO4 C6H5NO2 + H2O

14. *3&. 0 2 0&!. Lewis
1#2.2)" 2* " 2 # 0 # 0.
2* " .#2)" /0 0!!30 1&12 2 #" /01 *" 12

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15. .2 $. 00 2. 0!..2 /0/ . 2. . ..3! 2.
12 #"/01 *"2 # ! #2 #0 #*3&.0.#202 C
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0 #
16. 0) /0$.!.2!12".2/!10".)$
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0202. #)3 "2&02! &
30
17. 0 2 0/!.1 0.2 " . 10 C6H6
!..2 02. .2/!.1 # .212.1" . .!02. !.
&1C6H5NO21*3&.02$01&1
18. .../ #.2/!10"! 1"02.! #1.
0/#.Br2 100HCl.02.! #1.
. !.! ')2..#2+2& .2/!10& . # .212 $. 12" ) 0" 10!"
.
19.
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)201$.202.2 +.2 .)
21#$0.1$.202..)202.12 #0* #"2&02! &2 #/ */01 *! "2 +2 .2 "2
.)1#/02.02 ! "1$.21)2"
!01"&1"
20.
.22! 1212 ! .! #1.H2SO4 .!02.1*3&. 0 2 .). 2 # &" *! ! ')
.................................... .
21. ! 1HCl 12 ! 02.012 $.1)2"

2 12/ 2 # $.1 * 1$.2 2.
/* .! .2)2.2 .2 2.
. .2/! * 0 .)2. . 1$.2 # 2. .# $&!/.
. 2. . 03. # 02.*
2 #" 1 !0. 0/ 2. .*. 03. #
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2 #.1#0+"1$.202.100.*20!.. .0
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31
22. ) 2. .! .2)2. .# .2) 0# .2) 1 ! # .2) .
! # .2) 2 12.0!)20! 0. 2 . 2 .12.120! 2
23. 020/!.1#/.2 */.*.2 "H2SO4 - HgSO4 10. .!02.
0+10! .!02.
24. #/! !.0" )2..2/! *00!110.
02.2! 2.10 !01./$&!/.02.2 .2 #$&! #0&.
12 / 2 C . #12 ) 10!2&
25. #/! !.0" # .2/! * !&" 0 1 !. 1)22. Br2
. #12 ) 10!2&0+2.! ')2.
2".2/!.1".012 ) 10!2&
26.
.22.2/!.12".! #"&1"02
.2/!.12! Grignard . #/!)#1 2 # ! ')2 "
! 1".!02.0# ! .)
27.
.2 2 0/!.1 0.2 " NaCN . H2SO4 10 .. .!02.
. 0 2 0/!.1 #/.2 * /.*.2 "
H2SO402.2!02.12 !.&1
28. . 1#!+1020 2" .!.2& $" 01+10" 0 2 #" 1#2.2 *"
2* #"2&0+10& #0 #
. CH3MgCl + ...................... .......................
+H2O
- Mg(OH)Cl
&+ &+ &+

_
2+
CH3CH2MgCl + ........................ g(OH)Cl
&+
CH3COCH3 + .................... ................... +H2O
- Mg(OH)Cl
/ ................ + ................ CH3CH2CH2MgCl
32
_
&+ & &+

_
2+
+H2O
...................
- Mg(OH)Cl
29. 0 . .) 2. 12/. 2 # $.1 * 2" .2/!.1" 2" CH3CH=O 0
HCN 2 3 !21 2 C 2 # .! # # 1#/02.
02 2 C 2 ##!)3 #1$.2 2."2 !.)
0/01 01#2.2)2*
30. .# $&!/ 0 !.)2* C4H9Cl .20!02.00!).. ) /#. . .!02. 0. 2& !.+ 0+10&
. 12 0!$02. 10
0.*20! 1 12)2
31.
.221#!.1! .)" . H2SO4 12 #" C .!02.

.) 2 0 0! * 10 )
0! ! *20&"*! ! ')
32. 0 HCl 10 #2 .!02. &" *! ! ')
2 0!.)0 0 .. ) /#.
02.2!02.#!&"10
33.
.2 2 0/&1 2" CH3CH2CH2OH 0 ) /#. 2Cr2O7 .!
02. . . 0 2" 1#0" !. &1
0+ .2 2 0/&1 .#2" 0 ) /#.
KMnO4 .!02.) !.&1
34. . )C3H7OH .2/!0) /#. 2Cr2O7..!02. !.&101#2.2)2* ..3 *. &0! 1202.10. 2! #0!$00
0.3! !.1 1$.202. 12. 2 $+.2. 2 # 2! * 2 2! .!*! #)2..!.&1#0!.02.)2 1#2.2)"2* "2". )"0.
35. 2. !01 10" . ) 0!.0 0
..) /#. J2 .! 2. 2! . . 2 .! #) .)
/.. ) 0/+02.0) /#.KMnO4 ! "
2 !.&1 ..2/!0NaHCO3 .00#0!+02..!
33
36. 2. !01 .! #&10!.00

..) /#. J2 .! 2. 2! . . 2 .! #) .)
0+)2..2/!01$.202.0!.!#! .Cu2O.
37. . 2. 2 # ! # 2 # 20$2 * #0! *" Orlon 0.
-CH2-CH(CN)-CH2-CH(CN)-CH2CH(CN)-. .212 $ 0!" 0.
2 .)2 0.2/!10"1$.
2 2. 2. )!. 2 # #0! *" .2 2" .2/!10" .#2" 1#.0
#21$12&.0#!&.2&
02! & #! *2 #! "1$.21)/01+
38. . !%020 10 0 0) ! + 2 # .!.2& .. 2 3.)0
#.!.2!02...$!+.2 "1$.21)".2 ".220/!.1100&12"!+2"12".0)".)2..2/!.12!.2"
!+2" 10!" 2 0!2&1 .2 2 . /0 .!.2!02. ..
3.)0 10+12012 .212 $ 0) ! + 2 !.
!.&1
#.
Br2 10 CCl4
/#.
K2Cr2O7
CH3CH2OH
CH3CH=CH2
CH3CH(OH)CH3
CH3CH=O
CH3CCH
CH3COCH3
34
2/!.12!
Tollens
.)
/#.
J2
39. .1#!+1020100/122 2 #.!.2&/.!.2 "2 !.)! ')2"0$"02.2! "0202 ..2 *0 .2/!.12! . .020!2&1
CHCH
..................
NaCCNa
.............
/.2)/#.
H2SO4-HgSO4
CH2=CH2
........................
-
...............
MnO /H+
............
CHCH
CH3CH2Cl
......................
CH3CH2OH
.! #1.
H2SO4
H2/Pd, Pt, Ni
...............
..........................
40. .1#!+1020100/122 2 #.!.2&/.!.2 "2 !.)! ')2"0$"02.2! "0202 ..2 *0 .2/!.12! . .020!2&1
CH3CH2OH
...................
..................
..............
CH3CH=O
............
CH3CH(OH)CN
/.2)
/.
H2SO4
....................
CH2=CH2
CH3CH2ONa
CH3Cl
HCl
....................
......................
..................
CH3CH2CN
35
2/Pd, Pt, Ni
......................
41. .1#!+1020100/122 2 #.!.2&/.!.2 "2 !.)! ')2"0$"02.2! "0202 ..2 *0 .2/!.12! . .020!2&1

..................
Cl2/FeCl3
H2SO4
C6H6
..................
................
C6H5NO2
...............
C6H5NH2
HCl
..................
42. .1#!+1020100/122 2 #.!.2&/.!.2 "2 !.)! ')2"0$"02.2! "0202 ..2 *0 .2/!.12! . .020!2&1
CH3CH=CH2
HBr
........................
HCl
......................
.......................
-
Mg
.............
&+ &+ & &&+
........................
_
&+
/.2)
/.H2SO4
Cr2O72 /H+
.........................
0.
NaCN, H2SO4
..............
.......................
.......................
/.2)
/.H2SO4
H2O
CH3CH(CH3)CH(OH)CH3
.........................
43. .!%02012 .212 $ /122 2 ..2 *0 .2/!.12! .2

!..2 12"0.".)2".!.2&02.2! "
36
CH3CH2CH2CH2Cl
CH3CH2CH=CH2
CH3CH2COONa
CH3CH2CH(OH)CH3
CH3CH2COOH.

44. .!%02012 .212 $ /122 2 ..2 *0 .2/!.12! .2

!..2 12"0.".)2".!.2&02.2! "
CH3CH=CH2
CH3CH(CH3)CH2NH2
CH3CH(Cl)CH3
CH3CH(CH3)CN
CH3CH(CH3)COOH

45. .!%0202 #"1#2.2 *"2* #"2& !.+0+10&+
.,12".!.2&$"02.2! "
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+

,
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12
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0 2 0/!.1 0.2 " .
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49. .&.2.3#2..0.2"#0!"
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51. . 1. *. 0. .2. 0 2&
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52.
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38
53. . 1. *. .!.10# 2. 0 2 .2/!.1 2& 2!#0!/& 0

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1#0"1*3&.02$01&1
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5.4 !&210"2* #1&12) "0.2 )1

120.1$* #)$ ! 210" #. # *...3!0201$02).!/0.) #2 !0201)
1. . !.0/01..2/!.1"0.$"0+10" 0"/0
! *.. & *
2.
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3. ..!.)2.0. !.0/01. #1$.2 2..221$1

2 # */01 *0)".2) #C 0 / 20$)12 $0
4. To !.)0/01 #1$.202..22 #21$12 #/0-
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5. ! 11 #0 02.) 2! 10 .. .) 2!. 2!. # 0!$ #..) *3.)...).212 $...!.2!1 #0)2
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6. 10 /#. aOH 2 0!$0 . !&2 #2) /02 "
.0$!+.10pH 5 - 7, ! 12 #012.).12.).#)/#.
CH3COOH, ..!.2!0..2 #$!+.2 "2 #/.*.2 "
7. 10/#.aOH 2 0!$0.!&2 #2)/02 #.0
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2 #$!+.2 "2 #/.*.2 "
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40
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! 0. *.10" *
10. )2.2/!.1 #. //02.02$01&1
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11. )2 /0/ )2 .0"00)2* R-NH2 0..100"10"
! *20)2 0+10".#2".2/! *) 01$#!. *$. .
12. 020/!.1212 CH3CH2CH2Cl .!02.CH3CH2CH2OH1*3&.
02$01&1 CH3CH2CH2Cl2 CH3CH2CH2OH + HCl.
13. ) 2 .2/!.1 0)" .#. / # 0 KCN .!02. !.
&1 #$012 )!)2"0!11)20!.2 .C 101$102 .#. /
14. .2/!.1 # !..2 02. 02.* 2 # CH3CH2Cl . 2 #
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16.
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18. 020/!.1$&! #10CH4 12 /$#2 3&"0./#.2)..!.$0
0.2011!&$&! .!.+&2 #CH4.
41
19.
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20. 2 )! 2 # 0 # 0 2 C 1#/02. 0 2. /* 02 2 #

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21. *! ! ') 2" ! 1" 0! * 10 0 . 0. . /0#20
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22. .2/!.1 ! 1" HCl 12 CH2=CH2 $.!.2!02. &" .2/!.1
02! )3"! 1"
23. )2.2/!.1! 1"0! *12 ! .! #1.H2SO4, .!02.1 !.)0./* !.+0+10&
24. 1 ! # .2)0.00!0.12.0!)20! 101$102 ! #
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/$&! !
28. 0" !010" 100" . )0" !0 . .!.10#.12 * 0
! 1 .! #" &1" 10 .2/!.12! Grignard . #/!)#1
2 #! ')2 "! 1"
29.
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42
30. .2/!.1! 1"HCN 10.02./0/$.!.2!02.&".2/!.

1#!)3"! 1"
31. ) 2 .2/!.1 .. 2! # 0 0!110. 0! * .! #1. H2SO4
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32. )2.2/!.1$&! #2 #0.. )/#. .!
02.1 !.)0./* .0&
33. 0 2 !.1 0.2 " ! .)" . ! .)" 12 #" C
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34. 0 2 !.1 .0" .) 2" 1 0!0" . )0" 0 !.) 2*
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$12 ..
35. . 2 0 ! 1 0! * . 0/&1 2 # ! ')2 " ! 1"/0.! #) *0.) 2 .
36. 00/!.1) #/.*.2 "K2Cr2O7 100. )0 !.)2*
CH2+2O .!02. . . 0 2" 1#0" .! # &1 0 !.)2* CH2O.! #) *0 !.)2* CH2O2.
37. 0 0/!.1 ) # /.*.2 " K2Cr2O7 10 .0. .) 2" 1#2.2
1 0!0" . )0" 0 !.) 2* C4H10O .!02. . . 0 2"
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0 !.)2* C4H8O2.
38.
0 !01 .! # 02) !0 . .!.10#.120 0

0/&1.". )"
43
39. )2 /0/ )2. )0 !.)2* C4H10O/0. $!&.20

) /#. KMnO4 1#0!.020 )2 .#2 $0 1#2.2) 2*
2+
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41. +../.! #02! .).)2! . ! *0.$!1 1 #0300 #!).)$) /#.KMnO4.
42.
0 . .) 2" 1#2.2 1 0!0" . )0" 0 !.) 2* C4H10O
!0 . .!.$0 0 2 ..& ." .! #" &1" 0 2 .! #1.02. *.2.*2
43. +. . /.! #0 2 ! .) .) 2 ! .) ! *0 .
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KMnO4.
44. ./.! #&1 #.2/!0300 #!).+".
0..)/#.&/ #0...
45. 1$02 !..0 #0! *"! 1"0..!. .1 2"1$02" !."."2 # 0! *".)2 .#2).!$0
46. 2 )! 2 # .0 # #!$0 ." /01)" 0+ 12 )! 2 # #
.0 ##!$ #) /01 1
44
0$ .20*#1
47. 0.20!.1.2 #0.)./ #0NaOH 0+02. *222 #
48. ..#/!)#12&012!& 02.1.& 1
49. ./.2 ) ..0. *1 10.)!012. .!0.0!.0 ".!"2! 3"
50. .1!1. *.$ #.*20!. !!#.2/!112 1!)0!)101$102...1. *.
51. +. 2 .!.10# 0)" #012!. $!1 *2. &" 0! .
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45
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4. +!%20 2 #" 1#2.2 *" 2* #" . 2. ).2. 2& !.+ 0/01& # ! *2 # .) 2 1$1 2& /01+ C-Cl 2& 1#2.2
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5. )201$10)"/01 * 02. #2 /+1201$.22
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7. .!%0202"$"01+10"2&.2/!10& #!..2 *2.
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46
8. 0" .) 2" !." 0+10" C6H5-CH2-OH, C6H5-COOH, C6H5-CCH

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9. +!%202$01&1 2" .2/!.1" # !..2 02. .2 2
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10. .!%0202 #"1#2.2 *"2* #".2 ) ./* !.+0+10& #03. #.1"/)220".+".2"$"01+10"/*
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11. . !%020 2 #" 1#2.2 *" 2* #" . 2. ).2. 2& .+ #
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2&.2/!10& #!..2 *2..220/!.1HCl 10.0..)2".0" #..3!.20
12. +!%202"$"01+10"2&.2/!10& #!..2 *2..2 2 0/!.1 Mg 10 1 ! # $&!/ . 2 #/!)#1 2 # ! ')2 "
13. +!%202"$"01+10"2&.2/!10&# .212.1"02" 0"
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14. )20 . $ .2/!.1 $.!.2!02. &" .2/!.1 . /)1"
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47
16. 120 .2 .2/!.1 # . //02. 0 2 $ 01&1

CH3CH2Cl + CH3ONa CH3CH2OCH3 + NaCl $.!.2!02.&"#!)
3# .212.1
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22 ." .2/!.1" ..3! 2." . 2" 1#0" #) 2" 0" .#2
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22. +!%202"$"01+10"2&.2/!10&02" 0".! 2.
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48
24.
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25. +!%202"$"01+10"2&.2/!10&012" 0".!02. .) .. . !&2 2." . ) 0 /* 2 . C . )! .
!&2 2.". )02!.2 .C.)!
26. +!%20 2" $" 01+10" 2& .2/!10& .2 2" 0" .!02.
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27. "0. 1#2.2)"2* ".2 ) .2 #*! # !. *! ')2 " 2" .2/!.1" 2 # !& #2 # 0 .. ) /#.
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29. .!%0202$01&1 .. //02 1$.21)2 #*! #
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31. ..) 0/+02.! "..020/!.1) #/.*.2 "

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49
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32. +!%202 #"1#2.2 *"2* #".2" .10"2& !.+! ')2& # !0.! *% #.22 0/&1.0".)2"1 0!0". )0"0 !.)2* C3H8O.
33. 0. 2 .2/!.12! Tollens; +!%20 2 $ 01&1 2" .2
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36. 0" .) 2" !010" 100" . )0" . 0" .) 2" !0
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37. +!%20 2 #" 1#2.2 *" 2* #" . 2" .10" 2& 1 0!+ .
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38. " 0. 1#2.2)" 2* " . .1. 2 # 0! *" .) 2
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0NaHCO3; +!%202"$"01+10"2&.212 $&.2/!10&
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52
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2 *02! 1.#2
5. +!%20 2" $" 01+10" 2& .2/!10& 0 2" 0" .) 2 .# '&// 5 .! 2. . . ) R-OH .!." R-O-R
012!."RCOO-R/2 2! R-CN .02 . R-CC-R
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120 . 1$*0 !)2.1 )2. . $ &1 1#02$0 10
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12. 0!!%202././ $12/.2 #$.1 *2".2/!.1"! 1"
HCl 10. ..!3 2."2.#2)$! .2$01&1012./ #
+.2.2/!.1.#2$.!.2!02.&"02! )3! 1
54
13.
.2 2 .2/!.1 ! 1" HCl 10 ! .!02. 0. /*

1 0!+ .# $&!/& 120 0 1 2 $.1) 2" .2/!.
1" .) 2. 1 0! .#2 .# $&!/. .!02. 10 0.*20!
1 12)
14. . .. )&" . 2. .. . $!&.2 # /#. Br2 10 CCl4. 0
/* / .12 *" 1&0" # 0!$ # 2 /. 1)22. /.*.2 "
Br2/CCl4/. #012 .CH3CH=CH2.12 CH3CCH.
. . !%020 2" $" 01+10" 2& .2/!10& # !..2
*2.12 #"/* .#2 *"/ .12 *"1&0"
02120+" ! *002.!.&/./.1../.12+1 #0
.!+"0.2 .! #/.1.012 01&.
15. .!%0202"$"01+10"2&.2/!10&02" 0".).2
.2/!.12! Grignard . .2 .! # &1 .!02.
. !&2 2.". )02 !)20! /#.2).!).2)&C.)!
/0#20! 2.". )02!.2 .C.)! .
2!2 2.". )02 !)20! /#.2).!).2)&C.)!
16. 0.2 ) .2" !."&1"CH3CH2CH(OH)CN+!%202
$ 01&1 ." .2/!.1" .!.10#" 2" &1" .#2" . 0!
!%20 2. /./ $ 12/. 2 # $.1 * 0 2 .#2 !..
2 02.
17. .!%0202"$"01+10"2&.2/!10&02" 0"2 .#
$&!/ 02.2!02.20.10! #..10! .) *
18. 0 ! 1 +&1 10 .! #" 0+10" .! 2. #.#/!0"
#/!)#12& & /0 12 1$.21) .#/! # & . !%020
2"$"01+10"2&.2/!10&02" 0".!02..)2.2 .! # &1 . #/! #! .) * . #/! #
0# #2.) * 0 .2/!.12! .20!02. .!
#&1.0 !..2 02.#/!)#12"#.#/!"
55
19. 02120 0" .) 2" 1#2.2 1 0!0" . )0" 0 !.) 2*
C4H10O ! *. 0/& *$&!"./.1.120.!.2 #".#1/. +!%20 2 #" 1#2.2 *" 2* #" 2& ! ')2& 2" 0/&1" .#2+
-
2&. + .)2. 0/&21.MnO4 /H+ .Cr2O72 /H+ !0

.$!1 0.2 0/&1.0".)2". )0".#2"! 0 #..!.$0...)2..!.&! ')2. 0/&1"
20.
.0. .) 2!0" 30" 0!$0 . .) 2" . )0" #2.)
#2.).0# ! .)
. ...3!020..2/!.12! 02 .2/! *. 2!0".#2". )0"..2/!.12! 02 .2/! *) /* .
..2/!.12! 02 .2/!) .
. !%020 2" $" 01+10" 2& .2/!10& 2& .!.&
. +02..2/!.12!. #..3!.20
21. .! #&100) !.)2* &H2/.12+0)2

.02 .2/!.12! Tollens ./02. 3 !.2/!.1
. 012..!.&/0/ .002120 "0. 1#2.2)"2* "2"&1"
+!%20 2 $ 01&1 2" .2/!.1" 2" &1" 0 2 .2
/!.12! Tollens.
+!%20 2 $ 01&1 2" .2/!.1" 2" &1" 0 ..)
/#.$&! #
22. * 30"-1.-20!$ #.212 $.CH3CH2CH=O .CH3COCH3.
. ...3!020/* .2/!.12!.2. .)2.! 120 *2 .12
3-1.2 123-2..!.2!010.0..)2"
30" 1$.21)".2 "$.!.2!12 *$!+.2 "
.!%0202"$"01+10"2&.2/!10&12" 0" 3002.
1$.21)"2&2&
23. .!%0202"$"01+10"2&.2/!10&..&"02.! #
1. 02. * .2.*2 2& 0+10& . ! .) ! ../
! # $&!/ ./2! 0)
56
24. 0" .2/!10" $.!.2! 2. &" #0!1)" ! 1" +!%20

2 #"$ *"2* #".2. ).2./* #0!+! 1".+".
2& 0!+.)2. ..#2.! 2.
25. 2 0!.12! 0. /.1. 2. .2/!.12!. NaCN, H2O, HgSO4,
#/.2)/#.H2SO4.+".30.
.!%0202"$"01+10"2&.2/!10&02" 0" ! *0
..!.10#1 #012 0!.12! 2 #/! #! .) *
26. .2 #0 2. .)!.. .2/!.12!. Na, SOCl2, H2, #) 3,
#)H2SO4, Mg, Ni, H2O . #/.2)/#.H2SO4 - HgSO4.
.!%0202"$"01+10"2&.2/!10&02" 0" ! *0
..!.10#1 #002$!12&.2&.)2..!.&.2/!.12!.
. .)CHCH .CH3CH2OH 2 CH3CH2CH2CH2CH2CH3
.)C6H6 2.
.)CHCH .CH3CH2OH 2 CH3CH(OH)CH2CH3.
27. 030"0!$ 2..212 $. 0+10"
CH3CH2CH2CH=O
CH3(CH2)4CH3
CH3(CH2)3CCH
CH3CH=CHCOOH
CH3(CH2)3CH=CH2
CH3CH2CH2COOH.
02120 . 0. /#.2) . 0.!&0 2 0!0$)0 2" 0 3"
.2. ./.2/!.12!. #0./.1.0.
ii) #/.2)/#.Na2CO3 .
i) /#.Br2 10CCl4,
iii) .&.)/#.AgNO3.
28. 02030"0!$ 2..212 $. 0+10"
CH3CH2CH(OH)CH3
CH3CH2COCH2C3
CH3CH2CH(OH)COOH
CH3CH2CH2CH2CH=O
CH3CH2CH2COCH3.
. 02120+" ! *0.0.!+1 #02 0!0$)0 2"03" . /.2 #0 2. .2/!.12!. i) ) /#. KMnO4
ii) #/.2)/#.J2/KOH iii) 300 #!)
+!%202$01&12".2/!.1" #.!..2 0.2
2$!1 12 #300 ##! *
57
0$ .20*#1
29. 2! #0!0..1$#!).0/# 0!2)2 !0.0!.00! *1
. 0"!+20"*0"$!1 *2..2.!.10#2"+!%202
$01&12".2/!.1"02 ..!.10#02.
+" ! *0.2 #0)20! 0#.1212.2#.2.
30. 120 # 3002. . !!#.2 /!1 2 # 1. # * RCOONa
.0!!%202 2!) /!1"2 #.22. !#12&.!+
0/&.)2.! *$.
31. . .2 !. 1#02+ . !!#.2+ 0. 2. .2. 2& .#
0 1 #3 + &+!%202 1#2.2)2* 0)"22 #.2 "
.# /0202" /0"12" 0" 3002.. !!#.22 #/!1
+!%202"$"01+10"2&.2/!10&02" 0"2 .2
.# 0) .02.2!.02012 ." #..3!.20
32. . ..3!020 /* 1.2" $!10" 2 # 2 # # . . !%020 2
$01&12".2/!.1"02.2! "2 # 2 # # 10 .
0. $.!.2!12 /)22. 2 # . 10 2 0 020 .2 2"
2!2! #0!"
33. . 2..!.!0"0!!%202/./.1.02 .
3..02.2! 2.10.!.!0"
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#0! *"! 1".0)" #0! *"1#*&1".+".2&
0!+.)2. ..#2.! 2.
58
5.7. 110"! .2.

1. 0 2!. 2!. . + 0!$ 2. #/.2 /.*.2. CH3CH2OH,
CH3COOH .Na2CO3.
.
/0202 2!) 02 ! *0.0021 #010 .)
2. 2!. 2!. 0!$02. CH3CH2OH $&!" . $!1 1 #0
/ 20 $).2/!.12!
! 0 #./.12+1 #02 0!0$)0 2&/* & 2!+
0!.0 2 . .) .#2 . /.12+1.0 )2 20 0.2120
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2. +.. !.&1/.12+.2.0"
. 2002..)C, H .
$01$02 !..
.2/!0NaHCO3.
. !0202 1#2.2)2* 2"&1"

1202 ) 2 #.0! #10STP #.00#0!&0.! 11 #0mol 2"&1"10./#. #0!$0mol NaHCO3.
$02".2 "0"C: 12, H: 1, O: 16.
3. 02120.2./.*.2. #.! *% #100..)2".!.2&
0!2+10"0.)... #/20!.
. /#1. #.2! #CH3CH2ONa) 100!)
! 1mol .#."10L /.*.2 "HCl 0,1M
.01&)&/.*.2 "CH3COOH 0,1M .NaOH 0,1M
/ /..1. #10Na ./#12 #! ')2 "2".2/!.1"10
0!)
59
4. !0202 #"$ *"2* #"2&0+10&.+.1#!+1202"

$"01+10"
. &+ &+ &+ 3
_
&O
DNaCl + H2O
CH3COOH +
5. 9,2g ."#" !01" 10 *". )".2/!.1.!&"
0g Na. )2.2/!.1.#200#0!+0..! .! #%0.120!0)2 /.*1.0100!).1$.2120./#. #0302 .11#0!3 !
. 1202.11#0!3 !2 #/.*.2 " ..!3 2." .
2"$"01+10"2&1$02+.2/!10&
!0202 1#2.2)2* 2". )"

12010STP 2 ) 2 #.0! #
$02".2 "0"C:12, H: 1, O: 16, Na: 23.
6.
.22!.*1mol ." !."&1" #. 2002..)

2.12 $0.C, H ..!$.L CO2 10STP.
.
1202 .!).2)&C #0!$ 2.10.)! 2"&1"
00/!.1 Na 10mol 2"&1".!$.L H2 10STP.
.12+0.))2&1.2/!0NaOH, 0+/0.2/!
0NaHCO3. .! 20020.$&1..!3 2.".2 1#2.2)2"2* ...2. !02.12..!.&/0/ .
..2 10202.211."
7. 0 g !01" !." &1" # . 2002. .) C, H .

0/!.10 0!110. Na . 00#0!+. L #/! ) # 10 STP 1
1)22. 2" &1" 0.0!+0 . ! #%. L .2+ 10 STP.
0/0/ )2&1.2/!0NaOH, !0202 2"&1"
60
8. 2 #/!) / $0 2 # /. * 1$T = 12.0!

.2 " 2 002. 0 . 0#2
2 13.!)"
!1)2. .!$ mol ! - 0,2mol
.!."
CH
CCH
3
#.012 / $0 .#2)0.2
2!) . 22! ."g .
/.12+1.0)22 !$10.02.02..!.2012.0! 010 !11
. 120. ) 02.02 .! " ..20*#1.

12021*12.12&.0!& #0!$ 2.2012 / $0
021202.1#0.02201.&2 #.2! #01 #012
/ $0 0!"12.)0"0! *
.0&!1020.02.221.2+2 #0! *.+".2 #") #"
2& .0!& 1&2& # .) . 0!$ 2. 12 / $0 .2 2
/!0. )& 2& .!.& /0!.1+ 0! !.1. 2 # 1#12.2 "
/.2!02.12.0!$02.2 .Na: 23.
9. #!+120 2" .!.2& $" 01+10" .3 * .2.2.121020 2
1* R 02 .2 .*
. RBr + ..................... CH3CH2OCH2CH3 + NaBr
RI + ...................... &+ & 2&+ &+ + NaI
__
RCl + ...................... CH3CH2CCCH2CH3 + NaCl

/ RCl + ...................... CH3-CN + .................. .
10. +!%202"$"01+10")&2&/#.2+.2/!10&02" 0"
0./#.2)..!.10#1 #0
. 2 . CH3CCCH2CH3 0 0/!.1 .# $&!/ # 12 .2
!.&1
2 .!.CH3CH2OCH3 00/!.1.# !&/ #1012.2 !.&1
0*1
!$ # /* 1#/#.1 .2/!+2& . 2 .!.10#
2"0&1"
61
11. 0. #2 #0!.12! #0!$ 2.mol CH3CH2I.

. 0!!%20 0 2!) ! *0 $!1 +2." .#2 ) 2
!.!+2*.2..)!...2/!.12!.Ag2O, H2O .Na
..!.10#1 #0/.#.!.

120212.2 #/.#.!. # ! *0..!.10#1 #002 / .#2$!1 +2.")2 1)22.2 #
.# '&// # #/.2 #0
$02".2 "0"C: 12, H: 1, O: 16.
12. 10,9g 0)" .# !&/ # .20! 2. 0 0!110. #/.2 * /.*
.2 " Ag2O. +1.0 .2. 2 !. &1 # .!$0./.12+1.0)20$0.g.
. !0202 1#2.2)2* 2 #.# !&/ #
0!!%200 2!) ! *0..!.10#1 #0/.#.!.
$!1 +2." &" ./ !. !+2 * 2 &1 ..!3 2.".2"1$02"$"01+10"
$02".2 "0"C: 12, H: 1, O: 16, Br: 80.
13.
.2 2 0/!.1 0!110." #/.2 * .&!.2 " Ag2O 10 g 0)"
.#. / #.2/!.10) 1)22.2 #.#. / #.
.!$.g ..)"
. !0202 1#2.2)2* 2 #.#. / #
. . .#. /. . 10 0" 1)220" . ! *1.0 .
$!1 1 #0 ! 0 # . .!.10#1 #0 0 2 .!.&
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$02".2 "0"&+2&O%U
62
14.
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&11$.2120 .!."CH3CH2OCH3.
1)22. 2 # / # .# $&!/ # 0/!.10 10 . ." 0 2!
(&1+..!$0 012!." &+ & 2&+ &+ .
__
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120 2 .21 1." ..!3 2." 2" $" 01+10" 2&
.2/!10& #!..2 ..22"/* .!.&.!.10#".
+&! 2.")2
1# 1)22.2 #.# $&!/ # #/.2.02.g
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.2/!10"2. 1 2"
.!$.g .!.
# 1202.2 #012!. #.!$0
$02".2 "0"C: 12, H: 1, O: 16, Cl: 35,5.
15. 3 *! 1/ !10202"0+10"..1#!+10202".!.2&$"01+10"
. &+ &+ 2 & &+ 2
_
&+
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. ................ + ................. .
16. 1202&1 &+ 2 & =2 .!%202$01&1.".2_
/!.1".!.10#"2"
120121#$0.2"0"2&$+0+10& # .2/! * )2. .! 2. mol .#2" . 1#!020 2"
0"2&$+.#2+ #1+ #.2/! *0.#2" #!0...0$ * ! 0 # . .!.10#.10 .!.& 1)22. .#2"
2"$"&1"..2 10202.211."
$02".2 "0"C: 12, H: 1, O: 16.
63
17. ./#.) #mL ! #%000/!.10!110."/.*.2 "

HCl 10 . ./ 2 /#. .$0*. 0+10" ! .)
*.$&! *$ .+
. +!%202$01&12".2/!.1" #!..2 0.0
2 . /. 02. .! #1. 2& /* .!.& 0+10& 12
/#.
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0!$ 2.g ! . * "
$02".2 "0"C: 12, H: 1, O: 16, N: 14.
18.
.220/!.10!110."SOCl2 10g !01" 10 *". )"00#0!+0.0..0!&.)!.&0+10&2 # #

) "!01 "0L 10STP.
. !0202 !.)2* 2". )".!%202 #"/#.2 *"1#2.
2 *"2* #".#2"

/020 . 2!) 0 2 ! *0 . ! 1/ !1 #0 2 1#2.2)2* 2". )"
19.
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.!&) #L 10STP.
. 0!!%20. / 02 . !020.! 1/ !10202 1 2 1*12.1 2 # 0.2 " 2 / .#2 # . 0!!%020
!020 . $!1 1020 / 1." # 02 .!2 /0/ .
0 2 ! ()01 )2 2. . 201.2. # . ! *% # .2 2
000!.1..#2+.0.. /02

1202 ) (10STP)2 #CO2 #..!.$0.22!
.*1L (10STP)2 #0.2 "2&/* #/! .!& !020 . 2 0#020 . $!1 1020 2 . 201. 2 # 1 2 *
1."! 1/ !1 *2 #! *0 #0!&2.2 "
64
20. .g CH2=CH2 . $!&.2 # !1 1)22.Br2/.# #10CCl4.

/. 1)22. Br2 . $!&.202. .) g CH3CH=CHCH3 g
CH3CH=CH2 /g CH3CCH.)g CH3CCCH3.
. ./.20202 #".! *"./..2.* #1.10!
.1.01 !.)0.2&20.!.&#/! .!&
00!110.2&.)0!.)0 Ni. 022. !#12"
0!110." 2 # 2 .!0. L (10 STP) 0)" 0.2 " !0
1& #/! .!&
120 2 . 2 # 0 1#12.2 *
.#2 *2 #0.2 "
2. 1$02".2 "0" C: 12, H: 1.
21.
.22/..1! #10#/.2)/#.H2SO4 .2/!.10)

1)22.2 #! #! "0./* . +.! 1/ !1.0 .2. 2" 1)220" 2& /* . + . . 2" !.0
.212 $.g .0,6g.
. 02120 .0.. ). .. )
!020 "0. ) "10STP 2 #! 0 # #/.1.012 #/.2)/#.H2SO4;
0!!%20. / 2 .0..) . $!1 1.0 .
2 1 2) ! 1/ !1) 2 # 0.2 " 2& /* . + .
..!3 2." .!. . 2" $" 01+10" 2& 1$02+ .2/!10&
22. 0/..1mol 2 #.0 #10.!.)/#.H2SO4! *2 #

0,2 mol . )" , . 0/+02. !&" .) ) /#.
KMnO4 $&!" . /.1.120 .!. .#1/. . ! *20 2
.! #) *
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.!.& 0/&1
65
23. +..! 1/ !1 #021*12.10)"0.2 "CH3CH2OH .CH3OH

03.!)1.02"/* .!.2&0)/ #"
/ "
.010.&3g 2 #0.2 ".#2 *.! 11.0.2 12.)0" 1 0 H2SO4 /#. 1) KMnO4 0,5M $! . 03.10 12.0!) +/0" $!+. .2 2 /!0. 2" ! 1" 2 #
KMnO412 0..!.2! *1.0)200#0!+ 2...! )&2"
0/&1"2"CH3OH! "CO2 1*3&.02$01&1
5CH3OH + 6KMnO4 + 9H2SO4 3K2SO4 + 6MnSO4 + 5CO2 + 14H2O.
.12+1.0)2.2..+.mL 2 #/.*.2 "1.
/ "
0 !1 1)22.2 #0.2 "! 11.00!110... */.*.2 "2 .02!1.02.2 #.2 " #1$.2120
.12+1.0 )2 2. . 201.2. 2& /* 0)/& 2. . *2&" 1#.2
. 0 1 2. /0/ . 2" !+2" 0)/ # # 120 2 1*12.1 2 #
0.2 "
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$02".2 "0"&+2
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#/.2)/#.H2SO4 2 /#. #! *20. $!&.20$mL ) # /.*.2 " KMnO4 , 0+ )2. .2/!1 # !&" mol
CH3CH2CH=CH2 0 #/.2) /#. H2SO4 2 /#. # ! *20
. $!&.20%mL ) #/.*.2 "KMnO4.
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1$....2102012.0!&2.2. #. # *
2/2SO4
+ H2/Ni
+ AgOH
+ H2O
CH3CH=O + CH3MgCl
. 0. 1#2.2 2* . .10"2&0+10&

.+
+!%20 2" $" 01+10" 2& .2/!10& 0 2" 0" .) 2
&1.! 2.i) &1
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#02.2!012&1
2. 1$02".2 "0"C: 12, H: 1, O: 16.
26. .2 #0 2. .2/!.12!. Grignard CH3MgCl , CH3CH2MgCl . 2"
./0/0"CH3CH=O , CH3CH2CH=O.
. 02120 .) 2. .!.& .2/!.12!. Grignard . . .)
2" .!.& ./0/0" . $!1 1 #0 ! 0 # . .!.10#1 #0. ) .)2.! 120010..)/#.&/ #.1$.20.
+!%202"$"01+10".#2"2".!.10#"

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! 0 #..!.10#1 #0g CHI3
2. 1$02".2 "0"C: 12, H: 1, O: 16, I: 127.
67
27. !0" 30" -1 -2 . -3 0!$ # .) g 2& 1 0!+ !01&
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!0202 ) !.)2* 2&2!+. +.+
2. 1$02".2 "0"C: 12, H: 1, O: 16.
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69
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71
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2. 1$02".2 "0"C: 12, H: 1, O: 16.
36. 21,6g 0)". #..0$.0g H2.2 0. #! #%0
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72
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73
3.
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ii) 2 12020 1."
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74
2 .!/0.!2! #. )1"1*2 "/!0."

200 02.1" .)1 !.+.2/!10&2/!10"
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75
2. +!%20 2 $ 01&1 ." $" .2/!.1" 12 . 2

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CH3COOH
C2H5OH
C6H5OH
CH3-CCH
Na
NaOH
Na2CO3
NH3
/0"
76
3 .!/0.!2! #. )1"1*2 "/!0."

200 02.1"2/!10" !.+0+10&0
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................................................................................................................
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................................................................................................................
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2. ) 2" !." 0+10" CH3-CCH (I), CH3CH2OH (II), CH3COOH (III),
C6H5-CH2-OH (IV) .CH3-CC-CH3 (V).2/! *002.)2!
. )0"

(II), (III). (IV)

(I), (II), (III). (IV)
/
(I), (III). (V).
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77
3. 02120. .!.2&! 210"0. !"..10"

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4. 0,2mol CHCH .2/! *00!110.02. *.2! #
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78
4 .!/0.!2! #. )1"1*2 "/!0."

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# 02.
/0"
79
3. .1#!+10202"$"01+10"
ROH + ..................... RCl + .................... + ........................
RCl + ..................... ROH + .............................. .
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80
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81
3. . .!%0202"$"01+10"2&/* $+.2/!10&01
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82
6 .!/0.!2! #. )1"1*2 "/!0."

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83
3. .) .1#!+10202".!.2&$"01+10"
CH2=CH2 + HCl ......................
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0,5mol $&! #2 #
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. g CH2=CH2 ..2 *.2!#/! )&12 #"0.*20! 1)22.2101$10.#2 #..2 *.g CH3CCCH2CH3.

2. 1$02".2 "0" C: 12, H:1.
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84
7 .!/0.!2! #. )1"1*2 "/!0."

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85
3. * . )0"0 !.)2* C4H10O, 0"03. #1 !0.1" /.12+0 )2 . $!&.2 # /#. KMnO4
1 0
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..................................................................................................................
86
8 .!/0.!2! #. )1"1*2 "/!0."

200 02.1" 2/!10" 0/&1"..&" !.+
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87
2. 0. 2! #0!0$0mL 0*.2 "CH3CH2OH) ! 11.0

12.)0"/.*.2 "KMnO4 1 #0H2SO4.
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. CH3CH2OH.CH3CH=O
CH3CH2OH, CH3COOH.CH3COOCH2CH3
CH3COOH
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2010* 2 !. #.212 $0121&12.21
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88
1 .!/0.0..2 *!2! #. )1"

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2010* 2 !. #.212 $0121&12.21

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12 /#.

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90
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CH3+
CH3
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2010* 2 !. #.212 $0121&12.21

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/ 0.3#/2&12"0.)"
2010* 2 !. #.212 $0121&12.21
/0"
91
3. 12.0!)20! .) 2. 0/01. .! .2)2. # 1$.2 2. .2

2".2/!10"! 1"HCl 10. ! .0# ! 0.2

. &+ &+
&+ &+ &+

/ &+ &+ &+

_
&+ &+&+

0 &+ &&+

_
&+
&+
2010* 2 !. #.212 $0121&12.21

/0"
4. 0 !.&12"12"I) 02.2!00 0/&110..)
2" 0+10" 2" 12" (II). . 020 2 1$02 .3 1.2 .212 $1
(I)
(II)
A. #2.)
.. 0# ! .
B. #2.)
. #2.) *
+. 0# ! .)
. #2.
. #2.
/. #2.)
. 0# ! .
0. 0# ! .) *

/0"

+

,
1. .!%0202"$"01+10"2&.2/!10&02" 0".!02.
..)0 ./ !.!+2*
. ..#. /
..
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92
2. .0021020. .!.2&! 210"0.1&12"..10"

. 1$02 !..0 #0! *"! 1"0..!. .1 2"1$02" !."."2 # 0! *".)2 .#2).!$0
/0"
0 2 !.1 0.2 " 0# ! .)" . 0# !
.)"12 #" C .! #1. H2SO4 .!02.0./* .0&
/0"
,
!1 1)22.. )"0 !.)2* C3H8O 0/+0020/!.1/.*.2 "K2CrO7 1 #0H2SO4)2 /#. #! #%0 02 2 0/&1 . +0 1 2 2 0. 2& !.+
0+10& #0!$ 2.1.#2).12+0)22 0..#2)0$0.
30,6g, . 20 *2..)2./0/.2 *.020/!.10!110."300 ##! *1$.212.mol0!.!#! #.2 "
. 0. 1#2.2 2* 2"./0/".2 # "
+!%202"$"01+10"2&.2/!10& #!..2 ..22 0/&12". )"

1202.mol2". )" # 0/+.
$02".2 "0"C: 12, H: 1, O: 16.
/0"
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93

5.1. !&210" ."0 "

.
/

i) / ii)

i) . ii)
11.
12. i) / ii) .
13. i) / ii) .
14. /
15. .
16.
17. /
18.
21.
22.
23.
24.
25. .
26.
27.
28. 0
31.
32. .
33.
34.
35. i) ii) /
36. i) ii) .
37. i) ii) . iii)
38.
9. i) ii) .
10. i) . ii) iii) /
19. i) ii) .
20. .
29. /
30. /
39. .
40. /
1.
2.
3.
4.
5.
6.
7.
8.
41.
42.
43.
44.
45. i) . ii) /
46.
47.
48. .
5.2. !&210".212 $1"

/
.
+

.

+/
0

/
0
+
.

/

+0
.

.
+/1

./
.
+..+0

+.
/

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0

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+/
../

+.

0
13.

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+.

/
14. 0
0
++/
15. ./
0
1.
2.
3.
4.
5.
6.
7.
8.
9.
10.
11.
12.
94
5.3 !&210"1#!&1"
1. >.! .2)2.@ >.!.)2.@ >.#)!0"@ > *@ >02!.2)22."@
[C], [A], >02!.!2)22."@>)2.@> #2@

2. [ &+ &+&+ ], [ &+ &+ &+ ], [ &+ &+ @ >1 ! # .2)@ >! #
.)@>.#)!.@
3. > ) "$.!.2!."@>)0"@; > CH3COOH, C6H5OH@>) CH3COOH].

4. [CH3CH3],
[CH3CH2CCH],
[CH3CH(OH)CH3],
[ &+ &+ ],
[ +& & ],
[CH3CH(CH3)O: @>.# .)@>.).02#/ #@>1 ! # #.)@

-
5. >.1"@> .@>.#.& #@>HCl], [CH3CH2NH3+Cl ].

6. [.1"@>.212 $. .@>HCl], [CH3COOH].
-
7. [CH3COO: @>/0#20! @>Cl ], [CH3COOCH(CH3)CH3],

>..)"1 ! #012!."@
-
8. [ :CN], >/0#20! @ [Cl ], [CH3CH(CH3)CN], [0# ! . 2! ], [2 ! ')

$012 )!)2 #0!11)20!.2 .C 101$102 .2/!+].
9. [RO-H], [CH3CH2ONa], [R-OH], [SOCl2], [CH3CH(Cl)CH3], [SO2], [HCl], [/0].

-
10. [-OH], [CH3CH(CH3)O: ], [CH3COOCH(CH3)CH3@>..)"1 ! #012!."@

>0120! 1@>H2SO4@>)#/!)#1@
11.
!.&1
2/!.12!
!.)! ')
SOCl2
AgNO3/NH3
CH3CCNa
CH3CCCH3
CH3CH2CCCu
CH3ONa
12. .>AgOH], [CH3CH2OH]
>NaCN], [NaCl]
[CH3CH2CCNa], [NaCl]
/>CH3CH2COONa], [CH3CH2Cl], [NaCl]
0>CH3CH2ONa], [NaCl]
13. .>CH3COOCH(CH3)CH3], [H2O]
95
[H2O], [CH3CH2COOH]
[Cl2], [C6H5Cl]
/>C6H6], [3]
14. >@>! 1"@>.2.212.1"@>. *@>/ *@
15. >1@>00/ @>0& @>p@>0.&)@>0#!@>0202. @>@>0202. .02 1 @
16. ># .212.1"@>! 1"@>/.1 *1.@
17. >3@>H2SO4], [C6H6 + HNO3 H2SO4 C6H5NO2 + H2O
18. [Pd, Pt, Ni], [CCl4], [H2SO4], [..@> !01./$&!/.@>.# $&!/.@
> !010" 100". )0"@
-
19. [HCl], [02! )3 @>Cl ], [@>.# .2)@>Cl ], [CH3CH2+], [CH3CH2Cl].

20. [Markovnikov], [CH3CH(OH)CH3].
21. [02! )3"
! 1"@
>CH3CH2CH2+],
[ &+ &+&+ ],

[Cl ],
[CH3CH2CH2Cl], [CH3CH(Cl)CH3], [1"@ >@ > &+ &+&+ ], [CH3CH2CH2+],

[CH3CH(Cl)CH3].

22. [ &+ &+&+ ], [CH3+].

23.
24.
25.
26.
>..)"@>! .)@
[HCl], [.&@
>.0&@> !01&/!&/&@
[CH3COCH3], [CH3MgCl].
27. [CH3CH(OH)CN], [CH3CH(OH)COOH].

28. .[CH3CH=O], [CH3CH(CH3)OMgCl]
[H2O], [CH3CH3]
[CH3MgCl], [CH3C(CH3)2OMgCl]
/[CH3CH2MgCl], [HCH=O], [CH3CH2CH2OH].
-
29. >02@[CN ], [CH3CH(CN)O ].

30. [CH3CH2CH=CH2], [CH3CH=CHCH3], [CH3CH=CHCH3].
31. [CH3CH=CH2], [! 1@>CH3CH(OH)CH3].
32. >! 1@>CH3CH2CH(Cl)CH3], [KOH], [CH3CH=CHCH3].
33. [CH3CH2CH=O], [CH3CH2COOH], CH3CH2COOH].
34.
[CH3CH2CH=O], [AgNO3/NH3], [CH3CH2CH2OH].
96
35. [CH3CH2OH], [HCOO-], [CH3COOH], [CO2].

36. [CH3CH=O], [HCOO-], [300 #!)@
37. [CH2=CHCN], [! 1"@>/01+@> !&@>1@
38.
!.&1
/#.
K2Cr2O7
2! 10
!1
2/!.12!
Tollens
.)
/#.
J2
2!
.
2! 10
!1
2! 10
!1
2!
.
.!32"Ag
2!
.
0#).
2!
.
#.
Br2 10 CCl4
$
. $!&.
21)"
. $!&.
21)"
$
39.
CHCH
0!110..
NaCCNa
H2/Ni
/.2)/#.
H2SO4-HgSO4
CH2=CH2
HCl
CHCH
CH3CH2Cl
H2/Pd, Pt, Ni
CH3CH3
97
CH3CH=O
-
MnO /H+
CH3COOH
CH3CH2OH
.! #1.
H2SO4
CH3COOCH2CH3
40.
CH3CH2OH
Cr2O72-/H+
H2SO4
170 C
Na
CH2=CH2
CH3CH=O
NaCN - H2SO4
CH3CH2ONa
CH3Cl
HCl
CH3CH(OH)CN
CH3CH2Cl
/.2)
/.
H2SO4
CH3CH2OCH3
NaCN
2/Pd, Pt, Ni
CH3CH2CN
CH3CH(OH)CH
CH3CH2CH2CH
41.
C6H5Cl
Cl2/FeCl3
H2SO4
C6H6
C6H5SO3H
HNO3 - H2SO4
C6H5NO2
42.
H2/Ni
C6H5NH2
CH3CH=CH2
HCl
CH3CH(Cl)CH3
CH3CCNa
&+ 2 & =2
_
C6H5NH3Cl
/.2)/.
H2SO4
HBr
CH3CH(Br)CH3
HCl
CH3CH(OH)CH3
+
Cr2O72-/H
Mg
CH3CH(CH3)MgCl
CH3CH=O
CH3CH(CH3)CH(CH3)OMgCl
H2O
CH3CH(CH3)CH(OH)CH3
CH3COCH3
0.
NaCN, H2SO4
CH3C(CH3)(OH)CN
/.2)
/.H2SO4
CH3C(CH3)(OH)COOH
98
43. .. )/#. #/.2)/#.H2SO4, 2aOH, Cl

44. X: HCl , KCN - H2SO4 , H2/Ni , 0!110./.*.2 "H2SO4
45. CH3CH2X , CH3CH2MgX , +CHCH , CH3CH=O ,
CH3CH2CH(CH3)OMgX , CH3CH2CH(OH)CH3 , ,CHI3.
46. CH3CH2CH2OH , CH3CH=CH2 , +CH3CH(OH)CH3 , CH3COCH3 ,
CH3C(CH3)(OH)CN.
47. >00*0!..! # .@>0+ #0@>NaOH @>00*0!.! #
.@>.! #.2.@>1.& .@
48. >#0!@>3@>H2SO4], [0 - 10 C], [ !+/0"#)@>/#.2"@
49.
50.
51.
52.
>2!012!0"@>.! # .@>2!#0!/.@

[CH3(CH2)7CH=CH(CH2)7COOH], [.)!012.@>!)20!@
[Na], [K], [.!+ &@>Na@> @>..@
>#0!@>2!+@>C15H31COONa], [C17H35COONa], [C17H33COONa].
53. [NaOH @>1.& 1@>1.& 1@>. *2!#0!/ #@>1.& 1@>2 *2!#0!/ #@>0..! #+.2&@
54. >#/!)3@>0!)@>C17H35-], [)3@> "@
55. [Ca}, [Mg], [./#2.@>1#02+. !!#.2+@[Ca}, [Mg],>/.#2@
56. > /*1 .@>2 #) @>2!&1@
[C6H5CH3 + 3HNO3 H2SO4
C6H2(NO2)3CH3 + 3H2O
57. >.)!012.@>#/! )&1@>C], [4atm], [Ni].
5.4 !&210"2* #1&12) "0.2 )1

1. .)2.!0" #1$.2 2.100/01.12/...2..1 2.
100)0.1#0+"/0 ! *.. & *
2. )0* "02! &2 # */01 *C-Br 02.02.! "

2 02!.!2)20! 2 Br 0 . 201. 2 1$.21) 2 # .! .
2)2 "CH3CH2+.
3. $.2 2.) .221$1/01+C 0)20! 02!.!212 $0.$Mg.
99
4. To .22 #21$1)&!"/.3 !"02!.!2)22."02.*C ..!.01002 .02!) 2 # *0* #"0. +

_
201.2 1$.21)2".#)!." &+ & ).

_
5. . 2!0"0+10".2/! *02 2! 00#0!+ 2.".! 2.

6. /#.NaOH $0pH > 7. 02! 12 #CH3COOH0 #/020!+02.
2 NaOH0. 201..0+02.22 #pH. 0220 #/02!&1)"
2" 1)22. 2 # NaOH 12 /#. . 0!$02. 2 ." CH3COONa . 2
CH3COOH # 1#0$ #0 . ! 12 #0 #0+" 2 pH . 0+02. . .
. 2102!)20!2 #0. 201...02 $!+.2 #/.*.2 "
7. /#. NaOH $0 pH > 7. 0 2 ! 1 2" 3.)" . .2/!10
) 2 NaOH . 12 /#. . 0!$02. C6H5ONa . 3.) # 0!1
10*0 0/ 3.) /0 202. /.20!. .! #1. 2" 1" C6H5O- 2
pH 2 #/.*.2 "..!.000.*20! 2 #!.2 $!+.2 #/.*.2 "
/0..0
8. 2 !.) 2* C4H6 .212 $ * 2. .. CH3CH2CCH .

CH3CCCH3. ) .#2 ) 2 CH3CH2CCH .2/! 0 .&.) /#.
CuCl .1$.200!.!#! .
9. ) 2 $ 01&1 ! *20 )2 2 CH3CC- 0. 1$#! 1

CH3CC0.2 1##" *2 #CH3CC-1#0+"0. *.10" *
10. )2.2/!.1! *20)22.. #.)2.0.1$#!"10".)2

. )0"ROH 0.2.1## .2 #"1#0+"03. #.10) $.!.2!.
11. 2/! *2)1 01$#!)1 .0.10 .$

RNH2 + HCl RNH3Cl , RNH2 + RCOOH RCOONH3R
12. CH3CH2CH2OH .!02. 0 2 0/!.1 #/.2 * /.*.2 " Ag2O 12
CH3CH2CH2Cl,1*3&.02$01&1
CH3CH2CH2Cl + AgH CH3CH2CH2OH + AgCl.
13.
.22.2/!.1.2.12.2.2 2 Cl 0CN. !. !.&1
#! *20$0.2 C 0
14. .)Cl- #. .!*02..221$12 # */01 *C-Cl

.2.12.2..)2 #!)3 CH3COO:- .
100
15. !..2 02. .2/!.1 CH3CH2OH+SOCl2CH3CH2Cl+SO2+HCl, 0

. 201... .!* 2..)2 2!2..!.)0..!.SO2 .HCl#0+"
.2 #0!0$ #12 2!.0.!)20!.).g.
16. .2/!.10..3/! ..2.010.212.11 !! ."1#0+"

.)/ 12"0.!)20!.)
17.
!..2 02.#/!)#12 #! ../ #1*3&.02$01&-
1CH3CH2CONH2 + H2+ CH3CH2COOH + NH4+.
18.
.22.2/!.1 !0..2.2.12. *0Cl 2 .2./* 2.2!.

.2.2110!.2 .2 #CH4 0. 201..! *200. #0!$0
CH3Cl, CH2Cl2, CHCl3 .CCl4.
19.
.22.2/!.1.#2 / 202 2 # ! #2 ##/! !..
!0..2.2.12.0.)2 Cl.21 !0..!.$00.2

.0!$0ClCH2CH(CH3)CH2CH3 , CH3C(CH3)(Cl)CH2CH3 ,
CH3CH(CH3)CH(Cl)CH3.CH3CH(CH3)CH2CH2Cl.
20. 2! $.)p 0.!. .2) #0.*202.0#!.02./* 2! $.p2&02 +2 #.2)&C21+120.1$.202.."0202. "
/01)"/./.0202. #)3 "02! &2 .0
1 /*..10).2.2 .C .!102.&.2&.)2 00/ 2&/01+1
21. 0! 10! *12 CH2=CH2 .!02.CH3CH2OH.

22. 1$12 #/01 *.01.12.2 .C 02..)2 02! )3 +
2 1$.202..22020! #21$12 #/01 *H-Cl.
23. ! 102.1*3&.02 .).2 #Markovnikov, )20.!02.

! .)100.*20! 1 12)101$102! .)
24. 0/ 2. .*. .! #1 # 3.)0 2 02 3 !21 2 C

2 # 1 ! # .2)2 " 03.0 !)20! 3 !2 .) 2 02 3 !21
2 C 2 #! # .2)2 "1#0+"0.00!0.12.0!)20!
25. )2.2/!.12 #CHCH00!).!02.CH3CH=O.

26. !0.0. 1/ 20.)!012 "#/! !.."
27. .2/!10" ! 1" 12 2!) /01) . # * 2 .). 2 #
Markovnikov, )202 *! ! ')2".2/!.1"0.2 /$&! !
28. .2/!10" 2& .2/!.12!& Grignard 0 .! #" 0+10" 0.
.2/!10". /)1"1#0+"CH3OH/00./#.2)..!.10#.120
02 / .#2
101
29. )2"1 0!0". )0" /* !&2 2.0".!.10# 2.0 ! 1

3 !./0/"12 .2 .2/!.12! Grignard/0#20! 2."0! 1.."! ."12 .2 .2/!.12! Grignard.2!2 2."0! 1! .)"12 .2 .2/!.12! Grignard.
30. ) 2 020! #2 1$1 2 # 1 /01 * 2 # HCN ! *20 2 #!)3

CN:- 2 1#/02.02 023 !21 2 C 2 #.! # #
31. .2/!.1 /012 1$.21).. * ")&2"#/!)#1"2 #

.../ #
32. #2 .!02. 10 0.*20! .. . .2 2 # #2 # (03.! .).Saytzeff).
33. .!02.) 2 !

34. /0# ! .)/0/0.
35. .! # ..! 2.02 0/&1!&2 2.+. +)2.
..) 2 . 0! 10! */0!&2 2.. ).2.#) . .. / # )& 2 # .). Markovnikov, /0#20! 2.0" 2!2 2.0"
. )0"
36. !&2 2.0" . )0" / # . . 0 2" 1#0" ./0/0" ).
/0#20! 2.0"/ #) 02)0"0+ 2!2 2.0"/0 0/+ 2.
37. #2.) . 0# ! .) / # ./0/
*
#2.)/0) 02)0+0# ! .)/0 0/+02.
38. +. 0 02) #!$0 .212 $ /0#20! 2." . ) .) 2 .
!0..!.$00 0/&1
39. . )/0 0/+02.!.0.2!2 2."2 !.)2* C4H10O .212 $0) .2!2 2.". )0# ! .)
40. 0 .&.) /#. AgNO3 .2/! * . 1$.2 # .!32 .!*! #
) ./0/0".)$ 02)0"2 !.)2* C4H8O.212 $ */* 1 0!0"./0/0"..) 02) #2.)
41. 0 2 300 #!) .2/! ) ! . . 1$.20 0!.!#!
.Cu2O, 0+02 ) /#.KMnO4.2/! *. /* 0+10".1#0+"2 . $!&.2 #
42. 0 ..& 2& ./0(/+ 0 2 .! #1. 02. * .2.*2 .! 2.
!&2 2.0". )0"0..&2&02 +.! 2./0#20! 2.0". )0" 0+ 2!2 2.0" . )0" /0 !0 . .!.$ * 2 !.) 2* C4H10O
.212 $0 . 2!2 2." . ) 0# ! .) . 1#0+" /0
!0..!.$00.#2)2 2!)
102
43. 02 ..)/#.&/ #.2/!) ! .)..!02.$.!.2!12)2! .CHJ3, 0+. /* . )0". $!&.2 #2 )
/#.KMnO4.
44. 3 *.2/!0300 #!)0../0/ ./)&"./0/ #

/02. 3 !.2/!.10...
45.
.)!.2& #0!+! 1"1$.2 2.0.2/!10"! 1"
02.* 2& !& 2 # 0! *" 1*3&. 0 2 $ 01&1
CH2=CH-A ( &+ &+ ))2 $)2* 2 # #0! *"! *20
_
$
)2
#0! *"

0! *".
46. #. 1$.202.0.2/!10"! 1" !&.0 #.2

2" 0" 1#.0 #2 1$1 2 # /01 * 2& !& 2 # .0 # .
1$.21)"/01+102.*2&!+ #! *2 #
0$ .20*#1
47. . 00*0!. . 12. . 3002. *22. 0 2 aOH 02.2! 2.
12..212 $..! #.2.2. ./.$&! 2... .!* 2..)
2 0.)./
48. 2.2/!.1.#2.102..!.10#2&1. #+

49. .$ #00!02)22.10 !01. .0+12...#0!20! * 2. .)!012. . #0+" 2 /.2 ) !0 . 0!.0 2! 3"
#0!$ # ..
50. . !!#.2 /!1 2& 1. #+ 0+02. 12 1!) 0!) 020 .#2
0.1!020../)21$.2 #/#1/#2..! #.2.02
.112 .2 .1
51. . 0! #$!1 *2.0../.! #) *../(/! #.. )
52. . #0!! 1".! 2.0.2/!10"! 1"02.*2& !&2 # 0! *"1*3&.020$01&1

CH2=CH-A (-CH2-CH(A)-)
.)2 .! *20)2
#0! *"
103

0! *".
5.7 110"! .2.

1.
)/0
. .22.02&/.#2&CH3COOH .Na2CO3 .!.2!02.#1.0! #CO2
Na2CO30..".1#0+"120!022&1
2. .&1 C$H%O&.$%&
2/!0NaHCO3 $012 )!)2"2 #$12 .COOH & 2.
+.0&.)2$%./*.2 !.&
(1) $% $ % !. CH3COOH.
NaHCO3 0.100!110. )20..!.$0mol C2 V = 22,4L 10
STP.
-
3. .CH3CH2O + H2O CH3CH2OH + OH , !.! *20.1)/#.

CH3CH2NH2 + H+ CH3CH2NH3+
20
0,1mol
CH3CH2NH3 0.2 1##" *2".10 *"1"CH3CH2NH2!..+
2/!02 0!)CH3CH2NH3+2CH3CH2NH23+ /#.)

-
CH3COOH + OH CH3COO + H2O
20
0,1Vmol
CH3COO 0.1##"12 #.10 *" "CH3COOH,!..2/!

-
02 0!)CH3COO 2CH3COOH + OH /#..1)

-
/ HCCH + Na HCC Na+ + 1/2H2

-
HCC Na+ + H2O HCCH + Na+ + OH , !./#..1)

4. CH3CH(CH3)NH3+Cl
CH3CH(CH3)NH2
+CH3COO +NH3CH(CH3)CH3
5. . ROH + Na RO Na+ + 1/2H2

-
RO Na+ + H2O ROH + Na+ + OH , !./#..1)

CH3CH2OH
2,24L H2 10STP.
104
6. . C$H%O& +
$%&

2 $CO2 + %/2H2O
$ mol
1mol
.!$.L CO210STP $ $

0,1mol 2" &1" )2. .2/! * 0 Na / # mol H2
(STP!.12 )! 2"&1"#!$0. /. #.2/!0Na, /./..COOH .CCH.
&1/0.2/!0NaHCO3, 1#0+"/00!$0COOH02 NaOH
.2/! * 3.)0")$)&" . )0".2...2 #2* #RCCH.
-
!.&10.3.)02 .C .. 12 )!)2"/./

0.C6H5OH.
7. .L 10STP 2"&1"$ #.g, !.2.L .$ #.g
$0
. mol 2"&1")2..2/! *0Na 00#0!+ #
0,1mol H2 1mol 2"00#0!+0mol H2 , )20&1$012 )!)
2" . /. # .2/! 0 Na. 2/! 0 NaOH, !. /. .#2 0.
COOH.3 *3.)$0!
C$H%O& $%& & 3 $%./*.2
!.& .$% $ % CH3COOH.
-
8. . !..2 02..2/!.1CH3CCH + Na CH3CC Na+ + 1/2H2

.$0&". 201.2022&12 #1# *.! *mol 2&.0!&
3 * .0&2.!. #12.0!022&112.no$0&". 201.
20&12 #) #.1#0+"02.12 #0) #! "2..!120!

CH3CCH
.!$
0,2mol
.2.! 0,02mol
20
0,18mol
Na
0,02mol
0,02mol
-
CH3CC Na+
0,02mol
0,02mol
/2H2
0,01mol
0,01mol
2. !&0 .2/!.1 12 / $0 #!$ # mol CH3CCH .

0,01mol H2.
! 11 #012.)0"0! *.!..2 0.2/!.1
-
CH3CC Na+2 CH3CCH.+ !...# *.2.

1# mol 2&.0!& )202 .02.0! "2./0
105
9. . CH3CH2Br + CH3CH2ONa CH3CH2OCH2CH3 + NaBr

CH3CH2I + CH3COONa CH3COOCH2CH3 + NaI
CH3CH2Cl + CH3CH2CCNa CH3CH2CCCH2CH3 + NaCl
/ CH3Cl + KCN (NaCN) CH3CN + KCl (NaCl).
10. . CH3CCNa + CH3CH2Cl CH3CCCH2CH3 + NaCl
CH3CH2CCNa + CH3Cl CH3CCCH2CH3 + NaCl
CH3CH2Br + CH3ONa CH3CH2OCH3 + NaBr
CH3Br + CH3CH2ONa CH3CH2OCH3 + NaBr.
11. . CH3CH2I + AgOH (Ag2O + H2O) CH3CH2OH + AgI
CH3CH2OH + Na CH3CH2ONa + 1/2H2
CH3CH2I + CH3CH2ONa CH3CH2OCH2CH3 + NaI
12 1)22./.#.!..!02.)2.)0" .2/!10"0. 1 2". .!$" 1)220"!1 2.1012 $0 02!.. .21
2mol .) 2 1)22. 2 # CH3CH2I # /.2 #0 02.2! 2. 10 mol
CH3CH2ONa, 2. . .2/! * 1 2 0 2. #) . mol CH3CH2I .
.! 2.mol CH3CH2OCH2CH3.
12. . CBr
AgOH

mol
+
C
AgBr

mol
+
.!$.g C (A)

=

CH3CH2Br.
A: CH3CH2OH
CH3CH2OH + Na CH3CH2ONa + 1/2H2
CH3CH2OH + SOCl2 CH3CH2Cl + SO2 + HCl
CH3CH2ONa + CH3CH2Cl CH3CH2OCH2CH3 + NaCl

2 CH3CH2OH H2SO4/140 C
CH3CH2OCH2CH3 + H2O
13. . CgOH COH + AgX

.!$.g CH3CH2OH .n = 0,92/46 = 0,02mol.
!..2/!.1.mol C2H5; #$ #.g
0,02(122 + 5 + ) = 2,18 = 80 2 . ) 0.2 Br
. 2 #CH3CH2Br.
,. ! *1.0.$!1 1 #0mol CH3CH2Cl mol CH3CH2I.
14. A: CH3CH2Cl , B: CH3ONa , +CH3COONa
106
2/!10"
CH3CH2Cl + CH3ONa CH3CH2OCH3 + NaCl

CH3COONa + CH3CH2Cl CH3COOCH2CH3 + NaCl.
.2 #0 mol CH3CH2Cl

.!$. mol CH3CH2OCH3 0,8mol CH3CH2Cl 02.2!.
10.!..2.#) . mol 10012!..!$.mol 012!.88 = 105,6g.
15. HA: CH3CH(OH)CH3
HB: CH3COOH
. CH3CH(OH)CH3 + CH3COOH
CH3COOCH(CH3)CH3 + H2O
CH3COOH + NaOH CH3COONa + H2O
CH3CH(OH)CH3 + Na CH3CH(CH3)ONa + 1/2H2
16. HCOOCH3 : 0.)"0#012!."
HCOOH + CH3OH
HCOOCH3 + H2O
0,2mol
0,2mol
0,2mol
.2/!.1.46 = 9,2g HCOOH .0,232 = 6,4g CH3OH.
0/.2/!.1.2.010.212.1$"1 !! ." 0" #!0...0$ *! 0 #..!.$ *mol HCOOCH3 0.
.HCOOH > 9,2g ..CH3OH > 6,4g.
17. .) ./ $0 CH3CH2CN2
CH3CH2CN2 + H2O + HCl CH3CH2COOH + NH4+Cl
! ../ mol CH3CH2CN2 1mol CH3CH2COOH

$
1,2/60 = 0,02mol
$ mol CH3CH2CN.

!. 12. mL /.*.2 " HCl ! 12. mol CH3CH2CN2, 1#0+"12mL ! 12.mol CH3CH2CN2.
18. . C + SOCl2
CCl + SO2 + HCl
.mol
.mol
!.. . ..

.mol
0,2 =

C3H8O. #.2 CH3CH2CH2OH (I) .CH3CH(OH)CH3 (II).

0! 112. ).. */.*.2 "21$.21202! .. )0../01$.21200.
107
19. . 0.2&#/! .!& #! #%00!$0. mol CH3CH2CH3 .

mol CH3CH=CH2 #0!110%0
$0) L 10STP . .
+..! 1/ !1 #021*12.12 #0.2 ".#2 * ! *0.2 /.1 #010! #1 /#.Br2/CCl4 2 0!$00!11)20!..)
2,5 mol Br2, +120./010*10)2 1)22.2 #CH3CH=CH2# #0
2 #!)0.022/..12 #0.2 " )20
m = m!
0 #
m!
0 #..)2.
m!
0 #/42).
.L 2 #0.2 "0!$ #.22,4L CH3CH2CH3 .22,4L CH3CH=CH2

2.L 2 #0.2 "0!$ #. L CH3CH2CH3 .L CH3CH=CH2.
!..)2.*12&L 2 #0.2 "00#0!+ 2.. 2,5 =
30L CO2.
20. . C + Br2 CBr2 , C-2 + 2Br2 C-2Br4
)2".!.&0".2/!10"! *20)2
1mol #/ 20.0 #. $!&.20mol Br2 .
1mol #/ 20. #. $!&.20mol Br2.!.
2..mol CH2=CH2 . $!&.2 #.mol Br2
2.mol CH3CH=CHCH3 . $!&.2 #mol Br2
2.mol CH3CH=CH2 . $!&.2 #mol Br2
2./mol CH3CCH . $!&.2 #/mol Br2
2.mol CH3CCCH3 . $!&.2 #mol Br2.
3 *. $!&.202./. 1)22.Br2 0.
. / /.
0.2& !01&#/! .!& #! *20. 2002.1# .) mol .0!$0
0,130=3g CH3CH3 , 0,242=8,4g CH3CH2CH3 .56=11,2g CH3CH2CH2CH3.
21. .
.22.2/!.1! #00!).! 2./* . )0"1*3&.0

2"$"01+10"
CH3CH=CH2 + H2O CH3CH2CH2OH .
CH3CH=CH2 + H2O CH3CH(OH)CH3.
0/! 102.1*3&.02 .).2 #Markovnikov, .!02.
10 * 0.*20! 1)22. CH3CH(OH)CH3 !. . ) 0.
CH3CH(OH)CH3.. )CH3CH2CH2OH.
.
+
= 60 n.
+
+

= = mol

CH3CH=CH2 0,122,4 = 2,24L 10STP.
108
.2/!.1.mol
.1.02 0.2 . +10..)/#.2. +1.0.

#1.02 . #1$.212021#$0.! 11.012 /#. #
! #%0 .2 12.)0" ) /#. KMnO4 0,1M . 02!1.0 2 )
.#2 * #. $!&.2120
) 2 . 2 # .2 " # 1$.2120 # #0 2 1)22. 2"
CH3CH(OH)CH3..)2 ) 2 #/.*.2 "KMnO4 0,1M #. $!&.2120# #02 1)22.2"CH3CH2CH2OH.
$"01+10"2&.2/!10& #!..2 .0.
-
CH3CH(OH)CH3 + 4I2 + 6OH CH3COO + CHI3 + 5I- + 6H2O

-
5CH3CH2CH2OH + 4MnO4 + 12H+ 5CH3CH2COOH + 4Mn2+ + 11H2O.

22. i) 3 *mol 2 #.0 #/ #mol 2". )". )0.
2 ./)! ')2".2/!.1"! 1"0! *12 . . )
02 0/&12"/0.! #) *!.0.!&2 2." .
#/00! 10! *. 012!&2 2.. )0.2
CH2=CH2. !.2 . 0.2 .
...! . #2 02! 10! */ #/0#20! 2.
. ) . ! 1)22. !&2 2. *" 0+ 2 #2 /0 . 0
12/0#20! 2.. )
-
ii) 5CH3CH2OH + 4MnO4 + 12H+ 5CH3COOH + 4Mn2+ + 11H2O

0,2mol
mol
. $!&.2 2.mol KMnO4 2. .0!$ 2.10L /.*.2 "

KMnO4
23. . .g 2 #0.2 "0!$ #.mol CH3CH2OH ( .mol
CH3OH.
/* . )0" 0/+ 2.!&".)0,2 = 0,1mol KMnO4
5CH3CH2OH + 4KMnO4 + 6H2SO4 5CH3COOH + 2K2SO4 + 4MnSO4 + 11H2O
.mol
4.mol
5CH3OH + 6KMnO4 + 9H2SO4 5CO2 + 3K2SO4 + 6MnSO4 + 14H2O

mol
6mol
mol
. .

)2"01+10".. mol 2,3g CH3CH2OH .
mol 1,6g CH3OH.
00#0!+. mol CO2 V = 0,0522,4 = 1,12L CO2 10STP.
109
.g 2 #0.2 "0!$ #

mol CH3CH2OH
1$.212.mol CHI3 ( 0,2394 = 78,8g CHI3.

24. . 1$*02
CH3CH=CHCH3 + H2O CH3CH2CH(OH)CH3
0,2mol
0,2mol
5CH3CH2CH(OH)CH3 +
0,2mol
[

2MnO4-
+ 6H+ 5CH3CH2COCH3 + 2Mn2+ + 8H2O
0,22/5mol
x = 160mL.
25. . CH3CH(OH)CH3 CH3CH=CH2 CH3COCH3 +&+3CH(Cl)CH3

i) CH3CH(OH)CH3 H2SO4/170 C CH3CH=CH2 + H2O
ii) 5CH3CH(OH)CH3 + 2MnO4- + 6H+ 5CH3COCH3 + 2Mn2+ + 8H2O
iii) CH3CH(OH)CH3 + SOCl2 CH3CH(Cl)CH3 SO2 + HCl
.!$.g CH3CH(OH)CH3 ( 0,19mol CH3CH(OH)CH3
.g CH3CH2CH2OH (&1 0,01mol CH3CH2CH2OH.
!..2/!.1.1# mol CH3CH=CH2 .)2. .02.2!010CH3CH(OH)CH32 100/0,2 = 95%.
26. . CH3CH2MgCl + CH3CH2CH=O &+ &+ &+&+ &+
_
20J&O
&+ &+ &+&+ &+
_
+ H2O CH3CH2CH(OH)CH2CH3 + Mg(OH)Cl
20J&O
CH3CH=O + 3I2 + 4OH CHI3 + HCOO + 3I + 3H2O

0,5mol
0,5mol
..2 *2.mol CH3CH=O 44 = 22g CH3CH=O.

27. . 3-20!$02!2 2.. )3-1/0#20! 2..3
-3!&2 2.2!2 2.0". )0"/0 0/+ 2. !&2 2.0"
0/+ 2. ! " . . /0#20! 2.0" ! " 02)0" !. 2!2.2.0"
. )0"/0. $!&.2 #2 /#.KMnO4, 0+ !&2 2.0". $!&.2 #/1 ) 101$102"/0#20! 2.0"
5RCH(OH)R + 2MnO4- + 6H+ 5RCOR + 2Mn2+ + 8H2O
5RCH2OH + 4MnO4- + 12H+ 5RCOOH + 4Mn2+ + 11H2O
110

-1 . $!&210 0,04 = 0,02mol KMnO4 0!$0
= 0,05 mol

RCH(OH)R 2. .$ #.g

. )0" 0. 1 0!0" 1#0+" $ # ) 0) !.) 2*
C
!. 2&. +0.C4H10O.
28. . CH3CCH +H2O/H2SO4-HgSO4 CH3COCH3 H2/Ni
H2SO4/170C
CH3H=CH2 Br2/CCl4
CH3CH(OH)CH3
CH3CH(Br)CH2Br
i) CH3CH2CH2CH(CH3)CH3 CH3CCCH(CH3)CH3
CH3CCNa + CH3CH(Cl)CH3
CH3CCH
CH3CH(OH)CH3
&+
&+
_
_
ii) &+ & &22+ &+ & &1

_
_
2+
CH3COCH3
2+
29. . .!)2.1
A
+
Cr2O72-/H+
B
KOH/C2H5OH
H O/H SO
CH3CH2Cl
CH2=CH2 2 2 4 CH3CH2OH
CH3CH=O
Cl
H2/Ni
H2SO4/170C
CH3CH2Cl + Mg CH3CH2MgCl
CH3CH2MgCl + CH3CH=O CH3CH2CH(CH3)OMgCl
CH3CH2CH(CH3)OMgCl + H2O CH3CH2CH(OH)CH3 + Mg(OH)Cl
CH3CH2OH
CH3CH2Cl
+Na
.! 2
-
CH3CH=O
30. . CH3CH2OH , B: CH3CH=O
H SO
CH2=CH2 + H2O 2 4 CH3CH2OH
CHCH + H2O
H2SO4 - HgSO4
+AgOH
.AgCl
-
CH3CH=O
HCOOH: CH3CH=O + 3I2 + 4OH- HCOO- + CHI3 + 3I- + 3H2O

HCOO- + HCl HCOOH + ClCH3COOH: 5CH3CH=O + 2MnO4- + 6H+ 5CH3COOH + 2Mn2+ + 3H2O
CH3CH2COOH: CH3CH2OH + SOCl2 CH3CH2Cl + SO2 + HCl
CH3CH2Cl + KCN CH3CH2CN + KCl
CH3CH2CN + 2H2O + H+ CH3CH2COOH + NH4+
31. . CH2=CH2 + HCl CH3CH2Cl
CH3CH2Cl + KCN CH3CH2CN + KCl
111
CH3CH2CN + 2H2O + H+ CH3CH2COOH + NH4+

CH2=CH2 + H2O
H2SO4
3CH3CH2OH + Cr2O7
2-
CH3CH2OH
+ 8H+ 3CH3CH=O + 2Cr3+ + 7H2O
!)1010 12 #. 2 # 3 22 + 12.)0" ) # /.*.2 " KMnO4

..!.2!10)2.#2). $!&.2120
CH3CH=CHCH3
32. . CH3CH2CH=CH2
1- #2
#2
CH3C(CH3)=CH2
0# !
. )/0 0/+02.!.0.2!2 2."CH3C(CH3)=CH2

02! 10! *12 . ! *20) .. )
CH3CH=CHCH3
CH3CH2CH(OH)CH3 CH3CH2COCH3
/ +CH3CH2CH=CH2 CH3CH2CH(Cl)CH3 CH3CH2CH(CH3)MgCl

CH3CH2CH(CH3)CH(OH)CH3
33. . -1-40!$ #. )0"-2-30!$ #./0/0"
-2-40!$ #2"CH3CH(OH)CH3 , CH3CH=O
!. -4 : CH3CH(OH)CH3-2 : CH3CH=O ,
-1 : CH3CH2CH2OH-3 : CH3CH2CH=O.
! 12 #010/0.2..)2"2110!"30"300 #!) )20/.! #0 2" 30" # 0!$ # 2" ./0/0" .) 2" 30" # 0!$ # 2"
. )0" 2 1#$0. 0 0/!.1 10 /0.2. .) 2" 2110!" 30" ! 12 #0 ..) /#. 2 )20 /.! #0 2" 30" # 0!$ # 2"
0+10" #/ #2. 3 !.2/!.1
34. . CH3CH2CH2CH2OH
. $!&.21)"
- +
+ MnO4 /H
. $!&.21)"
CH3CH2CH(OH)CH3
CH3CH2COCH3
CH3CH2CH2CH2OH
H2SO4/170C
CH3CH2CH=CH2 + H2O
H2SO4
2
2! .
CH3CH2CH=CH2 + H2O
CH3CH2CH(OH)CH3
3CH3CH2CH(OH)CH3 + Cr2O72- + 8H+ 3CH3CH2COCH3 + 2Cr3+ + 7H2O

35. . 020/!.1.2! #. 2!0"0+10"00#0!+ #.! .
2!0"0+10"0.. )0"
) 0/+02.! " *) 0.!&2 2."C3H7CH2OH
/02. 3 !.2/!.10.CH3CH2CH(OH)CH3
+0.2!2 2."CH3CH(CH3)(OH)CH3
.3#/.2+02. ! " . 2 0 ! 1 0! * /0 &" *!
! ')2&1!.. )0.CH3CH2CH2CH2OH.
112
.g 2 #0.2 "2&. +0 ) !.)2* C4H10O 0.

= 0,5mol. 0 2 ! .*1 2 #" 00#0!+ 2. mol CO2 44 = 88g
CO2.
36. . .g 2 #. #00) !.)2* C.212 $ *10

mol ...02.2!. *10 !010"0+10"..2 *

mol
2&0+10& #! 12 #0

! 11.0 mol H2 . mol Br2, !.

= 0,8
C4H6
0 2 ! 1 0! * 10 mol 2 # . # C4H6 .! 2. mol 2"
.! #"&1"C4H8 ./02. 3 !.2/!.1.22 ..! 2.mol CHI3 394 = 78,8g.
113

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#2 12" 0)"+0+! "

&RS\ULJKW &  2! ./0#2"!0#."

!&210" ."0 " ...............................................................9

!&210"2* #1&12) "0.2 )1..................................40

!&210"1*2 ".21" .............................................................46

110"! .2. .........................................................................59

!2!. )1" ............................................................................73

!&210" ."0 " .............................................................94

!&210"2* #1&12) "0.2 )1..................................99

110"! .2. .......................................................................104

!)2. . 12 #"

0/)20" #1#0!12...".)2 $!10!.

0)2.3 !2 0!0$)0 2 #.!)2 "3#./ #$ #0..!.2!

2 2 "2 #.!)2 "3#./ #0!$ 2.

0.! .2)0!$0..!. 2  #$0120&20!2 #

.22020! #21$12 #/01 *C-Br 12 !.&1CH3CH2Br

.22 21$12 #/01 *C-MgCl 12&1 &+  &+ 0J&O 2

.22  #21$10)"/01 *C-H 12 0#  #2 ! *20 !.)0/01 #0!$0..!. 2  2  $012

.22!..2 12& !.+.2/!10&

+ AgOH &+  &+ 2+ + AgCl .

&+  &+ 0J&O 2

2. !.0/01. #1$.2 2.0..212 $.2.

 &+  &

 &+  &

&+ 

&+ 

6. )2" !."0+10" CH3-CC-CH3 (I), CH3-CH2-CCH (II),

(II) . (III)

ii) 03. #.1"/)220"

7. )2" !."0+10"CH3-COOH, C6H5-OH, C3H7-OH .CH3-CCH

8. ) 2" !." 0+10" C6H5COOH, C6H5OH, C6H5-CH2-OH .

12. 2".2/!10"  0"!..2  *2.02 $.1)#!)3"

#/20! )! 0/01) .1*0#2 0* "02! &

/ .) #/20! )! 0/01) .1*0#2 0* "02! &

#/20! )! 0/01) .1*0#2 0* "02! &

/ .) #/20! )! 0/01) .1*0#2 0* "02! &

 )  II), (III . IV)

 )  I . III)

 II), (III . IV)

14. )2..2/!.12!.: 2 + (I), & + (II),

 (II) . (III)

15. )2"/* $".2/!10"

CH3OH + Na CH3ONa + /2H2

$.!.2! 2.&"#!)3# .212.1

.220/!.1Cl2 10 #2 12 /$#2 3&".!02.

18. .2 #. *.2 #/ */01 *02.*/* .2)&C0..2-

12 $.10 10m .10 10m.

0 1,5410 10m10 10m.

19. )2 #"#/!  .0"C6H6, C2H4, C4H6 .C6H5-CH=CH2

.22! 1$&! #10!  .!02.

/ 0.$&! .!.+&2 #! . #

21. *! ! ')2"! 1"HBr 12  #2 0.2 

 /0#20! 2." #2# !&/

/ 2!2 2." #2# !&/ 

CHC-CH3 + 2HBr %U&+  &+ &+ 

CHC-CH3 + 2Cl2 &O&+  & &+ 

.2 2 .2/!.1 ." &1" 0 CH3CH2MgCl . #/!)#1 2 #

.220/!.10)".2/!.12! #Grignard10...#/!)#12 #! ')2 "! 1"! *20

25. 0.)0./#.2)..!.10#.100! 112.2

/ #/! ) #.2/!.12! #Grignard.

26. 0.2.#2#/! )&102)"0./#.2).! *%0. )

 &+  &+ &+  / &+  & &+ 

+, ,

#2 12" 0)"+0+! "

&RS\ULJKW& 2! ./0#2"!0#."

!&210" ."0 " ...............................................................9

!&210"2* #1&12) "0.2 )1..................................40

!&210"1*2 ".21" .............................................................46

110"! .2. .........................................................................59

!2!. )1" ............................................................................73

!&210" ."0 " .............................................................94

!&210"2* #1&12) "0.2 )1..................................99

110"! .2. .......................................................................104

!)2. . 12 #"

0/)20" #1#0!12...".)2 $!10!.

0)2.3 !2 0!0$)0 2 #.!)2 "3#./ #$ #0..!.2!

2 2 "2 #.!)2 "3#./ #0!$ 2.

0.! .2)0!$0..!. 2 #$0120&20!2 #

.22020! #21$12 #/01 *C-Br 12 !.&1CH3CH2Br

.22 21$12 #/01 *C-MgCl 12&1 &+ &+ 0J&O 2

.22 #21$10)"/01 C-H 12 0# #2 ! 20 !.)0/01 #0!$0..!. 2 2 $012

.22!..2 12& !.+.2/!10&

+ AgOH &+ &+ 2+ + AgCl .

&+ &+ 0J&O 2

2. !.0/01. #1$.2 2.0..212 $.2.

&+ &

&+ &

&+

&+

6. )2" !."0+10" CH3-CC-CH3 (I), CH3-CH2-CCH (II),

(II) . (III)

ii) 03. #.1"/)220"

7. )2" !."0+10"CH3-COOH, C6H5-OH, C3H7-OH .CH3-CCH

8. ) 2" !." 0+10" C6H5COOH, C6H5OH, C6H5-CH2-OH .

12. 2".2/!10" 0"!..2 *2.02 $.1)#!)3"

#/20! )! 0/01).10#2 0 "02! &

/ .) #/20! )! 0/01).10#2 0 "02! &

#/20! )! 0/01).10#2 0 "02! &

/ .) #/20! )! 0/01).10#2 0 "02! &

) II), (III.IV)

) I.III)

II), (III.IV)

14. )2..2/!.12!.: 2 + (I), & + (II),

(II) . (III)

15. )2"/* $".2/!10"

$.!.2! 2.&"#!)3# .212.1

.220/!.1Cl2 10 #2 12 /$#2 3&".!02.

18. .2 #. .2 #/ /01 02./* .2)&C0..2-

12 $.10 10m .10 10m.

0 1,5410 10m10 10m.

19. )2 #"#/! .0"C6H6, C2H4, C4H6 .C6H5-CH=CH2

.22! 1$&! #10! .!02.

/ 0.$&! .!.+&2 #! . #

21. *! ! ')2"! 1"HBr 12 #2 0.2

/0#20! 2." #2# !&/

/ 2!2 2." #2# !&/

CHC-CH3 + 2HBr %U&+ &+ &+

CHC-CH3 + 2Cl2 &O&+ & &+

.2 2 .2/!.1 ." &1" 0 CH3CH2MgCl . #/!)#1 2 #

.220/!.10)".2/!.12! #Grignard10...#/!)#12 #! ')2 "! 1"! *20

25. 0.)0./#.2)..!.10#.100! 112.2

/ #/! ) #.2/!.12! #Grignard.

26. 0.2.#2#/! )&102)"0./#.2).! *%0. )

&+ &+ &+ / &+ & &+

/ 02.2! 2 #CH2=CH212!. &+ &+ .

&+ &+ &+

/ &+ &+ &+

0 &+ &&+

29. 012$.2/!.1C4H8O + H2 C4H9OH 0./#.2).

!&2 2.0". /0#20! 2.0". )0"0 !.)2* C4H10

30. 00/!.1.. /..2 " 10$&! #2 .!02.

.22.2/!.12"&1"0..)/#.&/ #.! 2.

2! ..2 )CH3CH(CH3)COO .

III) III)

/ IIIII) IV).

2!&1" - 2.! #1.02. .2.*2

36. )2 "2&1#2.21 0!+.! #+0+10&0 !.)

39. 2! #0!.!.10#02.00/!.1#)0! !.1.C:

.2& !01& &

43. . !!#.2/!12&1. #+ 3002.12 )2.#2

/ 0!$ #12 )!)2 #"2)3 /.RCOO .

/ .)3 .* R-) ..#/!)3 2)! COO Na ).