Практикум органска хемија

Farmacevtski fakultet
Univerzitet
.
-
Sv. Kirili
Metodij

:
. - -
. -
. -
:
. -
. -
1.11
-

...

( )

...

..

...

IR

(I)

: VSEPR
, ()

(II)

,

1

, 1
, 2
+ : , 4
, 6
2
: 1.
, 7
, 8
1 (), 10
+ , 11
, 13
2 ()
: 2.
, 14
, 15
, 16
2 ()
: 3.
, 17
, 18
+ , 19
, 20
3

, 21
Fisher- , 22
, 23
4

, 24
(Canizzaro- ), 25
+ , 26
, 27
5

, 28
, , 29
+ , 30
6

, 31
, 32
7

, 33
, 34
8
(I):

, 35
, 36
, 36
9
(II):

, 37
, 38
, 39
10
(III):

, 40
, 40
, 44
, 46
, 51
IR , 55
, 58

,
, , ,
, .

, ,
,
.
, ,
.
, , .

.

,
. ,
.
,
. , .

- , , ,
, .
.
/
!
2005
R (risk) S (safety) .
R (risk)

,
R . , R11 " " ( ),
R34 "" ( ).
, R23/24 "
".
.
S (safety)
R S

. , S8 " ", S24 "
", S36/37 "
".

R23/24, " ",
.
R S :
1.
:
T
R: 45-25-26-34
S: 53-26-27-45
R45 -
R25 -
R26 -
R34 -
S53 - ,

S26 -

S27 -

S45 -

2. (HMPA)
:
T
R: 26/27/28-45
S: 53-54
R26/27/28 - ,

R45 -
S53 - ,

S44 -
3.
:
T
R: 21-23/25-40 S: 36/37-38-40
R21 -
R23/25 -
R40 -
S36/37 -

S38 - ,

S40 - ,

,

MSDS (MaterialSafetyDataSheet)
.
2
1.
HIGHLY FLAMMABLE F
EXTREMLY FLAMMABLE F+
.
,
, ,
.
100 .
GLP ( )
,
.
( ) .
,
, : , , ,
, , (), , , ,
.
.

,
.
(. flash point)
.
, (. 2,) (. Mg
) .
LiAlH4 2
.
E
2.
EXPLOSIVE

. : Na
, - .
.
/ .
2.

. ,
, , , , ,
.
O
3.
OXIDISING

( ).
( . )
.
. .
, , .
, , (VI) .
C
4.
COROSIVE
.

.
.
: , ,
, , .
,
, ,
.

.
,
.

. , .
HCl
.
Xi
5.
IRRITANT
,
. ,
: -
, , .

: , -, , , .
.
.
6.
Xn
HARMFUL
TOXIC
,
. ,

. ,
,
(, , , .) .

, , , ,
, , , , , , ,
, .

, .
T+
7.
VERY TOXIC
(CANCER SUSPECTED AGENTS)

() .
,

.
!
cancer supspected agents
( ).
,
.
/ :
, , , , , :
; : ;
: , ; ,
(VI), , ,
; , .
.
,
() .
.
.

(Materila Safety Data Sheets - MSDSs)
http://ptcl.chem.ox.ac.uk/MSDS/carcinogens.html.
ENVIROMENTAL DANGER
7.

.
.
8.

.
,
" , !".
,
.
II.
1.
. , ,

, , .
!!!
()

, ,
.

.
. ,

, .
,
.
. 1
.

,
.
6
2.
:
- , , , .
.
- .
, ,
, ,
.
- ( )
- :
+ ; + ; (III) /
+ ; / 2 + .

,
.
, .
.
1.

-
-
Ppm
mg/m
200,0
400,0
20,0
1,0
0.1
5.0
250.0
1.0
10.0
0.1
50.0
200.0
300.0
50.0
10.0
50.0
50.0
400.0
1000.0
200.0
400.0
2.0
0.1
50.0
400.0
100.0
200.0
1.0
0.5
10.0
10.0
5.0
100.0
10.0
10.0
366,0
965.0
100.0
3.3
0.25
19,0
32.0
894.0
5.0
0.7
154.0
965.0
11.2
1050.0
200.0
180.0
270.0
1464.0
1914.0
890.0
1200.0
3.0
0.4
249.0
980.0
610.0
256.0
5.1
4.7
25.0
70.0
25.0
383.0
32.0
65.0
3.

.
.

!
.

. ,
, ,
.
.
,
.
,
,

.

.
III.
:
-
.
.
.
-
. ,

.
.
- , ,
, .
( )
.

.
- ,

IV.

:
1.
2.
3.
4.
5.
1.
.
( )

.

. .
( )
(5-10 cm)
.
2. () , ,
, , .
( ) .
Ac. borici
NaCl NaHCO3. ( )
.
3. :
a. (H2SO4, HNO3, HCl, HF, CH3COOH) ,
(10 min)
.
9
5% NaHCO3 . ,
.

.
b. (KOH, NaOH) ,
, .
. ,
.
.
,
1%
.
c.
.
.

( ) .

, ( )
.
d. -
10 (
).

.
, ,
.
4. . ,
.
,
,
.
, .
SO, H2S, ,
2 .
.
, , , ,
. HCN

.
5. .
.
. .
10
(
, .)
!!!

!!!
V.
,

. .
1. , ,
,

( )
2.
.
,
.
3. (KMnO4, K2Cr2O7, AgNO3)
.
4.
, .
link-:
MSDS (Material Safety Data Sheets): MSDS
.
, , , , ,
,
.
MSDS
http://msds.chem.ox.ac.uk/
R- -
http://msds.chem.ox.ac.uk/risk_phrases.html ( R- )
http://msds.chem.ox.ac.uk/safety_phrases.html ( S- )
11

...
1.

;
2. ,
, ;
3. ,
(g / mL / mmol) (, , ,
.);
4. ,
.

.
!!!
,
, ( )
.
, .
...
1. :
- , ,
- ;
- ;
- ,
;
- , /
2.
/;
3. ,
!!!
4.
()
.
...
1. ;
2.
3.
;
4.
.
12
, :
1. , /
.
2. .
3.
4.

5.
6.
7.

8. ,
, ,
.
9.

.
10. .
11.
.
__________.20_____.
13
R/S
R36
R 26
R23/25
S3
S36
S3/7
14

, ,
( /, ) :
:
1. -
2. -
3. -
15
. -
.
-
:
16

.
.

. , ,
, ,
. ,
.
.
,

. ,
,
-
.

.
( )
( )
.
" "
,
.

( 1).

100ml
1.

18
:
100 ( ) 100 mL
7.5 g - () (- 100 7.5 g /100 mL)
20 ( ) 0.25 g -
100 mL () (- 20 0.25 g /100 mL)
(20-25 )
.
:
100 , 7.5 g
100 mL . 20 ?
: 20 0.25 g (7.5 g - 0.25 g = 7.25 g)
: 7.25 g .

.
:
() 6 g
?
:
100 7.5 g 100 mL .
7,5 g
6,0 g
100 mL
X
6,0 g 100 mL = 7,5 g X

X = 80 mL
: 6 g 80 mL .
temperatura

.

( ). ( )
.
(1 2).
1. ( )
19
temperatura
1 .
.

( ) .

.
( 2)

.
.
2. ( )

.
" " ..
/ ( 1).
1.

,,
, , ,
,
,
,
,

,

.
,
. ,
;
; .
20

.

, .

.
:

1. -

. ,
.
2. ()-
,
,
(,
) .
.
.
3.
,
. ,
0 (
.
,
.

. .. ,

.
4.
Buchner . .
(! !)
5.
.
( ),
.
21

.

.

.
,

.

.

:
1.

.
2. ( )

. .
.
3. (
)
,
, .

:
4.
5.
6.
...
1.

(, , ).
,
,
, , .
(
).

(, , ) . 10-20 mg
22
- ( ). 1 mL
. - ( )
(++) (-).
10- (0.5 mL)
. (++),
(+).
.
( ).
- (++), (+)
(-).

.
2.
-
2 g .
:

. -.
, . -
( mL) .
.
o

.

,

.

.

(1-2 min).
-
. ( % = /
100).
23
I -

-
(g/L)
++ ; + ; -
______________________
II
= ________g ;
___________mL
( - ).
24
3.
mpred = ________g
% = mpo / mpred x 100
mpo =_________g
% =
4.
:

, .
.
++
-
+
++
-
++
++
++
-
++
++
++
++
+
++
+
+
++
++
0.8g/100ml 0 5g/100ml 78.

25
1.
12 g ?
_____________ mL
2.
()?
_____________ g
3. (g) ()?
4.
_____________ g
26

,
. 1.
2. -
.
, , /
.

.
- , .
-

. o,
(
). ..
,
.
H2O
CH2Cl2

() ,
:
() -
=
() 2

( ):
() CH2Cl2
~
() 2
46
35 g / 100 mL
5 g / 100 mL ( )
:
35 g/100 mL
=
=7
5 g/100 mL
, ,

().
100 mL 5 g
100 mL .
=7.
g,
5- g, :
X g/100 mL
7=
X = 4.375 g
(5-X) g/100 mL
, 100 mL
4.375 g 100 mL 5 g
. 0.625 g . 87.5% .. 87.5%
.
,

. , 2 3
.
, 100 mL
50 mL ( )
3.89 g , 1.11g , 0.863 g
. 4.753 g 95%
.
2
, .
, , .
,
1 .
,
(), ( . NaCl) .
47
NaCl
,
.

.
,
, .
( )
,
. ,
.
.
( ).

- ,
.
:

.
:
( ) -
, , (, ) .
( ) -
, ().

.
-
/
, .
- - ( > 4)
- - .
(/)
/
.
.
48

1.
+
+
+
/
+
/
+
-
(. )
( / )
() .
(. ) (Na-)
, . NaOH.
, .
(. HCl)
.

.
(N)

5% NaOH
(A)
(N)
(A)
(A)
(B:)
(N)
(N)
5% NaHCO3
Na-

+
(Na A)
5% HCl

+ (BH Cl )
pH~9
.
NaHCO3
pH~1
Na-
.
HCl
.
HCl
pH~5
(A)
(A)
(B:)
..
.. - ,
.. .

.
! !
49

. , ( ),
.
1.

.
(. ).
(. , , )

. ,

( 2).
!!

( !)
2.
50

. /
(3 ).

.
( !),
,
! ( 2).
( ).
(
)!

2,

,
() ( ).
.
( )
. ( ) .

mL .

,
.

!
...

( -) ( 4-).
2 g 1:1 20 mL
(CH2Cl2).
, 2
20 mL 5% HCl. -
/.
, 2
20 mL 5% NaOH. -
/.
/ 20 mL
(CH2Cl2) -
.
, - 20%
NaOH ( ).
, ( ,
, ) .
, -
. HCl, .
, .
4-
% m / m
100.
51
1.
:

:
*

( - )
-.
-.
52
2.
.@
org. k-na:
org. baza:
CH2Cl2 __________ ml
mL
5%HCl
CH2Cl2
20% NaOH __________ ml
5% NaOH __________ ml
CH2Cl2
25% HCl ___________ ml
(

53
3. :
m (.- ) =
% - (recovery) =
m (. )=
% (recovery)=
% (recovery)=
4. :
:
.
/ 10 25.
4g 100ml , 100ml
50 mL ?
54

. ,
, .

.

. e
, .
,

.
, :
-
- ( )
-
-

. .
.

.
.
,
.
, .
, ,
.
.
1.
,
. ,

.
46

:
.
:
(P)
PA PB .
P = P A + PB
: ,
(P)
PA (X) .
PA=PA XA

.

.

.
.
2.
( ; - - - )
-
( )
( ). 1:1
( ).
. ,
, 50 % ,

- .
47
(
) .
,
.
. 80
.
( )
85% 15% ( ),

() .
,
. , ,
.
()
.

80 30-150 . , ,
, , . 30 ,

, 150 ,
. 3
.
3.

. 2/3
.
.

.
(.. Y ),
48
.
Y-
. .
.
, .

.
( 4. )
Liebig-
Allihn-
( )
Graham-
4. ()

,
().
..
( T 150 )
.

,
(. , , ,
).

.
,
/ .
.
, .
,
. , ,
,
.
49

1.
: 12.5 mL
mL

45-88
0.5

88-90
4.8

90-180
0.9

180-183
4.2

,

80 .
,
. ,
.

(y-).
5.
,
( )
( ) .

. ,

.

(
Vigreux- (1), Widmer- (2),
(3) .
50
5.

.
. ,

. , n-
n- .
1:1
3 ( 20-30 ),
3 95%
. , 2-15
. ,
0,5 .
( )

.
.

.
, 150
.
, Clisen-
, -
, Liebig- .

.
, ,
Clisen-
( ) .
(
6).

.
51
6.

.
, 20 .
10-20 mmHg 100 .
0,1 mmHg,
150 .
( 7).

. .

. , ,
, .
760 mmHg 200 ,

20 mmHg 90
7.
52

,
.
. (!
). ,
()
.
, a

.
100 .

.
, .
,
( = 126 ). 90 (760
mmHg). () (90 ) (
)
.
= +
760 mmHg = 525 mmHg +
= 235 mmHg
, (mol)
, :
P () 235 mmHg
n (mol- )
=
P () 525 mmHg
n (mol- )
0,448 mol / 1 mol ,

, 0,448 mol-a 1 mol ,
( ()= 114 g/mol; ()= 18 g/mol) :
0,448 mol () / 1 mol ()
51 g / 18 g ,
, 51 g 18 g 74 % () .
,
35 : .
.
( /
),
( 8). ,
. .
.
.

53
, ,
.
)
8.

8.
, .
, (),
lisen-
.
54

, .
.
.

(
- ). ,
, ,
.
.
)
9.
()
9. , .

. , ,
(cold finger .
) . 9
.
46
1.

( )
46
2. :

: (y-)
(-)
V
(mL)
T (C)
()
.
____________ :
47

. o
( chroma = , graphien = )
,

.
,
:
.
.
( ).
1.

( )
(
)
/ Size exclusion chromatography
()

( , )
-

( )
(
)
,
() ( ) -/ (
). ,
.
:
.
.
48

(Thin layer chromatography - TLC)
(TLC)

.
TLC (0.2-0.04 mm) (
). () ,
(SiO2).
. (Al2O3)
.

. .

: - ( 1).

.
( )
UV TLC .
CF2
O (CH3)
2C
O Si
O
H
Si O
O Si
O
R1
R
(
)
1.

( ).
2 .
.
,
.
.. ( 1).
( ,
) .
49

1.

n-
n-,
i-

..
TLC
. ,
.

TLC (0.5-1 cm )
( ) .
.
TLC
(l) , .
,
.
50

,
( ) .

.
. TLC
,
.
,
.
/
. ,
( ) (
).

.
,
() TLC .

TLC . ( 1. :
).
()
.

.
- -
TLC
. 2
:

,

- ( )

,

- ( )
(0.5-1 cm
TLC )
.
TLC

. , .
UV , ,
51
-
(.
, KMnO4
, , ,
, ,
.).
(Rf )
TLC Rf
(. retention/retardation factor). Rf
(cm) TLC .
Rf 0 1. Rf
.
( )

Rf
.
Rf . Rf
. Rf
, . , , ,
.
()
Rf =
(b)
4,8 cm
Rf =
8 cm
Rf = 0,6
.
, TLC
: (St), ()
.

.
52
TLC .
TLC .
TLC.
TLC.

( ).
.
...
...
1. reaktant
2. reakciona smesa
3. produkt
53

.
. ,
().
.

.
.
.
2.
K :
1.

.
.
.
.

.

, .
2.
54

,
, .
3.
,
, .
( )
. .

( )
flash ( )
4.
,
.
( ).
TLC.
TLC.
( Rf ) .
3. (TLC)
55
....
( )
(254 nm).
TLC : , 2 , .
TLC (~0.5 - 0.7 cm
) (1. -, 2.
, 3. 2-).
. !

. .

TLC .

. ~5 mm
( ). :
(5:5). 0.5 cm .
UV 254 nm.
UV
. Rf
.
4. TLC
56
.
(TLC)
1.
2.
3.
: (
):
57
( Rf
)
58
59
()

1 . ,
, ,
,
.

50250 .
,
.
.
(1-2 ) ( ),
(> 3 )
( ).

Tiele-
Tiele-
.
. ( =1-1,5 mm) ,
,
(50 cm).
. 3-4 mm
.
Thiele-

60
,
, 1
/.
(
)
,
(~10 )

. ,
7
. (1-2
) .
MelTemp

.
.
Tiele- .
Koffler-

.
.
50-250 .
.
.
61

,
2 ,
(. 123-125).

.
,
.
,

(. sintering).
( =1).

(2).
.
()

(T1)
(T2)
...
I ( 1)
max 2
.
, (
Thiele- ).
.
II
( 1) .
(
1). ( 1)
50:50 ( ).
( 1).
62
.
()
I
,

_____________________________________
_________________________.
63
II

( 1 + )
1
2
.
.
-
3- -
76-80
43-47
135
157-158
165-166
157.5-161.5
80.5
48.1
135
158
165-166
172.5
:
64

4 :
1.
2. ( )
(/, )
3.
4.
1.

.
.

1 mL .
~ 20mg ( ) 5-6 ( )
.
.
:
H2O: - ( 5
) (, ,
, ) .
5% HCl, NaOH NaHCO3
!
5% HCl: - ()
5% NaOH: - ( ,
)
65
5% NaHCO3 : - ( ,
). CO2

.
.
H2O
( < 6 C )
( < 5 C )
( < 6 C )
( < 6 C )
( < 4 C )
( < 5 C )
( )
5%
NaHCO3
5%
NaOH
5%
HCl
H2SO4
+
+
+
+
+
+
* - HCl , - . H2SO4
66

.

COOH, -NH2 OH.
5
( ). ,
(. ), .

.
NaOH
, 5-9% -
NaOH. pH , 14, a
(pKa) < 12 .
(pKa~5) .
(pKa~10) .
.
O
-
RCO- + H2O
RCOH + OH
OH
O-
+ OH
+ H2O
NaHCO3
; 5% - pH
~9. pKa < 7,5. ,
(pKa ~5)
.
. . 4- pKa = 7.15. 5% - NaHCO3.
NaHCO3 CO2.
O
RCOH
HCO3
O
RCO-
H2O
CO2
HCl

HCl . HCl
. ,
.
67
RNH2
HCl
RNH3
Cl

.
/ ,
.
.
ROH + H2SO4
O
RCR + H2SO4
RC N
H2SO4
+
ROH2 + HSO4
OH+
RCR + HSO4
+
RC NH
HSO4

.

. , ,
.

/ .
2.

.
.
.
.
, , ..
3.

(C,H,O) (N,S,P X)

.

.
( . ), ( .
) (. , ).
68

1.

.
: 1.
2. . 2.
(Baeyer ) .
- .
0.5 mL 1
KMnO4.
.
.

. , ,
.
R1
R3
R2
KMnO4
R4
vi ol et ov
R1
OH
R3
R2
OH
R4
MnO2
kaf en
2.
0.5 mL H2SO4 K2Cr2O7.
.

. .
R1
OH
K2Cr2O7
R1
O
R2
R2
Cr
3+
zel en
3.
.
0.5 mL (~1 mL) AgNO3 (Tollens ). NaOH.
( ).
RCHO
2 Ag(NH3)2OH
RCO2NH4 + 3 NH3 + H2O + Ag

sr ebr eno ogl edal o
Dokolku ispituvanot soedinenie e vo forma na kristali se zemaat ~50mg i se r-raat vo 0.5ml voda
69
4. ( )
0.5 mL - NaOH.
.
( ).
.
!
O
R
I 2, NaOH
CH3
RCO2Na + CHI 3
H 2O
svet l o ` ol t
pr eci pi t at
5.
0.5 mL
FeCl3. - .
6 Ar OH
Fe ArO
FeCl3
36
+ 3H
+ 3 HCl
6. ( -, -)
1-2 mL 5% NaHCO3 .
CO2 /
Na2CO3 NaHCO3
. CO2
.
NaHCO3
RCOOH
R COONa +
CO2 + H2O
7.
0.5 mL 2 mL HCl 0.3 g
NaNO2. - - 1 mL NaOH.
.
- .
OH
ArNH2
aq NaNO2
HCl
Ar
OH
+
N N
di azoni um jon
N
70
Ar
8.

,
. SN1
.
, .

, sp2
( ) .
AgX.
0.5 mL AgNO3.
,
Cl -, Br I- .
RX
AgNO3, EtOH
R ONO2 + AgX
X = Cl, Br, I
bel - kr emast -` ol t
(
), ,
.
, , ;
, 3,5- . ,
,
, .
(, ).

.
...
(1-7).
: , , , ,
, , , ,
, , , 4-, .
:
-
- ,

-

71
, (1-7) :

, HCl, NaOH NaHCO3
. H2SO4
!
(
)
.
:

!!!
72
,
.

.
(+/-)
H2O
5% NaOH
5% NaHCO3
5% HCl
(1-7) :
1,2,3,4,5,6,7
-
H2O
5% NaHCO3
5% NaOH
5% HCl
73

( / / ) :

_
74
(+) :
/
KMnO4
K2Cr2O7
FeCl3
Na2CO3 /
NaHCO3
Ag(NH3 )2NO3
NaNO2;
-
AgNO3
.
:
75
* : , , , , , ,
, , , , , 2, , 4-, , .
76
(IR)

(IR)
/
.
(
) .

( ,
).
.
.
, ()
cm nm.
Slika 1. Elektromagneten spektar
, () , Hz ()
(1Hz =1 /).
: , , ,
= c / = c /
, 2.9979x108 m/s
:
E = h = hc /
h Planck , 6.6x10-34 Js
(cm-1),
:
(cm-1) = 10 000 / (m) = hc

, !
: ,
. .
2,5-15 m IR
4000-666 cm-1.

(1-10 kcal/mol)
(
77
(IR)

).
, IR

.

IR
().
( ).

.
VALENTNI VIBRACII (VO RAMNINA)
ASIMETRI^NI
SIMETRI^NI
DEFORMACIONI VIBRACII (VO RAMNINA)
SCISSORING
ROCKING
DEFORMACIONI VIBRACII (NADVOR OD RAMNINA)
TWISTING
WAGGING
2. :

:

( 1500 cm-1)
:
o (
. C-H, O-H, N-H (2600-3700 cm-1), C-C, C-O,
C-N (800-1300 cm-1)
78
(IR)
o / . /
(2300-2000 cm-1)
(1900-1500 cm-1)
(1300-800 cm-1)
valentni
vibracii
deformacioni
vibracii
IR .
- ( )
. ( %) y-.
IR IR
().

, .

(cm-1).
(, , /strong, medium, weak)

79
(IR)
.. ,
(), , /
IR
.
IR

- (Neat) (CCl4, CHCl3, CH2Cl2)

NaCl ( IR )
:
- KBr KBr
- (Nujol) - Nujol .
,
2900,
1460 1375 cm-1
-
NaCl

IR C-H
~3000 cm-1.
.
1300 cm-1 , ,.
.
(, ,)
IR
.
1
C-H (~3000 cm-1) :
80
C-H - sp3 ()
3000 cm-1 (3000-2850 cm-1)
Abs.
max
-1
(cm )

-1
3000 cm
C-H

-1
3000 cm
2950
CH sp
(IR)
C-H - sp2 ( )
3000 cm-1.
Abs.
max
-1
(cm )

-1
3000 cm
C-H

-1
3000 cm
3050
CH sp
1600
C=C
. C-H
-1
3000 cm .
-1
C-H 3000 cm .
C-H - sp (! )
3300 cm-1. CC
2250 -2100 cm-1.
Abs.
max
-1
(cm )

-1
3000 cm
C-H

-1
3000 cm
3300
CH sp
22502100
CC
2
C-H ( 3000)
( C-H ) O-H N-H .
.
OH
o

3300 cm-1. C-O 1260-1050 cm-1
81
(IR)

-1
3000 cm
C-H

-1
3000 cm
Abs.
max
-1
(cm )
34003200
12601050
OH
C-O
O-H .
-1
CCl4 3620-3670 cm .
,
. 1.
o
OH (
C-H ) () .
.
= 1730 cm-1

-1
3000 cm
C-H

-1
3000 cm
82
Abs.
max
-1
(cm )
33002500
17251730
OH
C=O
(IR)
NH2
NH2
N-H ( )

-1
3000 cm
C-H

-1
3000 cm
Abs.
max
-1
(cm )
34503400
1NH
NH

-1
3000 cm
C-H

-1
3000 cm
Abs.
max
-1
cm )
34503400
2NH
3
( C-H
). .
I.
2200-2300 cm-1
(/) (/)
83
II.
1650-1800 cm-1
(=)
III.
=
1500-1600 cm-1
(IR)
- ~2200 cm-1.
. -
3300 cm-1.

-1
3000 cm
C-H

-1
3000 cm
Abs.
max
-1
cm )
3300
CH sp
22502100
CCH
CN CC,

C=O 1700-1720 cm-1

-1
3000 cm
C-H

-1
3000 cm
Abs.
max
-1
(cm )
1700
C=O
o 1700-1720 cm-1.
C-O , , ~ 1200
cm-1.
Abs. max
-1
(cm )
1735
1000-1300
C=O
C-O

-1
3000 cm
C-H

-1
3000 cm
84
(IR)
o 1725 cm-1.
W ~ 2800 cm-1 C-H
.
Abs.
max
-1
(cm )

-1
3000 cm
C-H

-1
3000 cm
2800
1725
C-H
C=O
o ( OH )
1760-1690 cm-1 .
,
. OH . C=O
1320-1210 cm-1 C-O .

-1
3000 cm
C-H

-1
3000 cm
85
Abs. max
-1
(cm )
3100-2500
OH
1760-1690
1320-1210
C=O
C-O
( C-H - sp2 )
Abs. max
-1
(cm )

-1
3000 cm
C-H

-1
3000 cm
3000-3100
CH
2
sp
1650
./
C=C
(IR)
86
Abs. max
-1
(cm )

-1
3000 cm
C-H

-1
3000 cm
3100-3000
C-H
1600,
1470,1400
C=C
(IR)
(, )
-1
(cm )
4000-3000
~3300
3200-2600
~3000
-1
- 3300 cm
O-H
2-3 - 3450-3400
-1
cm
N-H NH2
NH NHR
,
-1
( , ) 2500 cm
, (
) C-H
-1
3000 cm
3000-2900
-1
cm
-1
3100-3000 cm
O-H
C-H ( )
C-H
-1
, - 2150 cm
CC
2300-2100
-1
, 2250 cm
, 1715 cm
CN
-1
C=O
-1
1715 cm W
-1
2850-2750 cm
-1
1780-1500
, 1735 cm (C-O-C,
-1
, 1200 cm )
-1
, 1715 cm O-H
-1
3200-2600 cm
-1
C=O
-1
87
C=O
C=O
~1640 -1680 cm
~1650
C=O
, - 1650 cm
C=C
1600, 1580, 1500

-1
cm
C=C
88

(I )
: , ,
, VSEPR (valence shell electron pair
repulsion) , ; ;

: Spartan Build Spartan View;
;
; VSEPR;
.

SpartanBuild
SpartanView .

.
.
.
SB Spartan Build, SV Spartan
View.
.
" ",
.
. ,

(
).
1.
,
.

.
. ,
.
89
1. (SB)
Model.
,
.

. :
,

, , .
2. ,
.
: VSEPR
Geometry Angle.
(
).

Geometry Distance.
().

(Valence Sheel Electron Pair Repulsion -VSEPR).

.
. ,
(
) -
( )
. ,
.

(, , ) ()

().
(
) .

.

.

.
90
1. VSEPR
0
0
0
1
2
4
3
2
3
2

109.5
120
180
<109.5 (107)
<109.5 (105)
3. (SB) : , , , , ,
, , , , , .
:
:
H-C-C

C-C, C-H,

,
()

.
.
0,5 .

(-) (+).
.
, ( + - ).
( /esu)
( cm) = e x d. Debye (D).

.
4. (SV)
:
NH3, H2O HF.
SpartanBuild (NH3, H2O HF) ...
+ ( ) SpartanBuild
/
.
91
:
-
-
.
Van der Waals-

. ,
.

.
, .
5. (SV)
() :
H2, HF, CH4, CH3F CF4
6. (SV) : ; ; ;
; ; ; ; ; ; .
/ ( )

SpartanView :
File -> Open -> Carey ->...
92
...
Chapter 9
Molecule
Chapter 9
Molecule
Chapter 1
Molecule
Chapter 1
Molecule
Chapter 1
Molecule
Chapter 1
Molecule
Chapter 1
Molecule
Chapter 1
Molecule
Chapter 1
Molecule
Chapter 16
Molecule
Chapter 4
Molecule
Chapter 22
Molecule
Chapter 4
Molecule
Chapter 18
Molecule
Chapter 20
Molecule
Chapter 15
Molecule
Chapter 19
Molecule
figure 93
figure 93
figure19
figure19
problem1
problem1
problem1
problem1
problem1
Formalde
figure 44
Phenol
figure 44
figure 22
Methylam
Problem1
Figure 20
file
Acetylen.sxf
Ethylene.sxf
Ammonia.sxf
Water.sxf
Hydrogen.sxf
Hydroge1.sxf
Methane.sxf
Fluorome.sxf
Tetraflu.sxf
Formalde.sxf
Methanol.sxf
Phenol.sxf
Chlorome.sxf
Aceticac.sxf
Methylam.sxf
Dimethyl.sxf
Ethylace.sxf
II

(
)
93
III (VSEPR )
*
()
()
**
x y
-
*N-H2
*=
{ ,

** #
IV
( )
C-H

( )
*-
H-C-O
*N-H2
H-C-N
*=
C-C-O
H-C-X
:
94
V ,
, ,
() .
NH3
H2O
HF
:

()
(D)
H-N (NH3)
H-O (H2O)
H-F (HF)
(-),
( + - )

H2
CH3F
CCl4
cis-1,2
trans-1,2
=0 ?
95
(D)
VI
} 3 H2O,
NH3 HF .
H2O
96
NH3
HF
:
1. VSEPR ( )
?
H O
H C C H
H
Cl
CH3
H3C
N CH3 CH3 CH2 C O H
2. , ?
?
3. |:
Csp3 - Csp3 ___________, Csp2- Csp2 ___________, Csp Csp____________
H-- Csp3___________, HCsp2___________, H-- Csp___________,
Csp3 - Osp3 ___________, Csp3 Osp2___________,
4. ?
97
5. ?
6. 1- 74.
{? ({ )
98
II
II
( )
: ,; ;
; - ;
: Newman- , , ,
; -
;
I
1.

Newman- .
Newman-

. Newman- -
/ .
. ,
.
1. ,
Newman- .
E
Newman-
. 360.

, .
,
. ( !!!;
). .
.
.
.
2.8 kcal/mol.
Sparatn Build .
C-C . ( Internal
rotation SpartanBuild)
99
II
2. SpartanView (folderite): Chapter3 -> Molecule >Problem 3. (a,b,c) .

.. .
3.2 kcal/mol.

. H-H
H-CH3 . 0.4 kcal/mol
H . ,
.
. ( H-H 0.9 kcal/mol H-CH3 1.3
kcal/mol)
3.
.
.
(gauche, anti syn )
.
C-C : anti gauche.
CH3 ( C1 C4) anti. ( /
, C1, C2 C3 C2, C3 C4)
180. .
CH3 60 gauche .
CH3 0.9kcal/mol.
anti- gauche- .
H-H H-CH3 .
(1.3 kcal CH3-H 0.9 H-H)
3.5 kcal/mol 3.4 kcal/mol.
CH3
0 .
4 6 kcal/mol. ( H-H
0.9 CH3-CH3 2.2 4.2 kacl/mol.
(CH3).

- .
,
. , 80% anti
20% gauche.
100
II
Dihedral Geometry
( 2 )
.
2.
4. (/) SpartanBuild
- .
( )

. .
V , (a b)
. V (c d) (
a b). d. a.
(e). f. c e.
b.

2 .
.
/ 4
/ .
. -
. :
- 1 4 2-3 5 6 (A)
- 2 5 3-4 6-1 (B)
- 3 6 4-5 1-2 (C)
5. (CH3- ) (CH3-
)
. :
101
II

3 5
- -1 - -3 -5, CH3
(1. 2.)
Newman- 1-6 2-1,
. gauche- ( ).
6. SpartanView (folderite): Chapter3 -> Molecule >Problem 4.
.
7. SpartanView (folderite): Chapter3 -> Molecule >Problem 5. .
( ) ?
8. :
a) trans-1- -3- t-
b) cis-1- -3- t-
c) trans-1- -4- t-
d) cis-1- -4- t-
*tert (t)- = 1,1-
102
II
.
( )
I
Newman-
Newman- ( ) A,B C.
Newman- (1-2 3-2)

:
1-2
3
2
1
3
2
1
3
2
103
3-2
II
Newman-
C2-C3 .
.
E
N
E
R
G
I
J
A
diedralen agol () (pome|u

dve metal grupi)
II

:
1. 3 1. / 2.
2. -4 1. / 2.
-1
3. -6 . 1.
2. ?
1
4
104
II
,
Newman- gauche .
.
1.
2.
3- .
3
5
1
3
5
Newman-
1-6
2-1
1-6
2-1
( ) 1,3-
?
( )
1.
105
2.
II
III
(/) ((CH3)3C- CH3- )
:
:
(CH3)3C-
CH3-
trans-1-t--3-
cis-1- t --3-
trans-1- t --4-
cis-1- t --4-
( +
) .
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
:
106
107

: 2
:
:
C6H5NH2
. HCl
(CH3CO)2O
CH3COONa

0,027 mol
0,027 mol
0,032 mol
0,050 mol
:
O
NH2
NHCCH3
1. HCl 2.(CH3 CO)2 O
3. CH3 COONa
!!!
!!!
65 mL , .
HCl.1
. , 0,2 g
5
50 .

,2
12,5 mL .
.
,
.
:
: 113 .
...
IR
.
108
:

( ).
O
CH3
C
NH2
+N
O
CH3
C
O
O
CH3 C
C
O
CH3
H
CH3
O
NH
CH3
NH
H
+ CH3 COOH
+ CH3 COO

, ,
.
O
C CH3
N
C CH3
O
O
N
C C H3
O
+
C C H3

,
.

.
109
,
.
.

. ,
.
HC l
NH 2
NH 3
, ,
.

.
O
NH 3
C H3
NH 2
C H3
OH
110
NH2
1 .H C l 2 .(C H 3 C O ) 2 O
3.
C H3C OONa
p r o d uk t
p r o d uk t
p r o d uk t
2 C lS O 3 H
p r o d uk t
NH3
p r o d uk t
H3O
H2NS O2
p r o d uk t
111
NH2
(http://riodb01.ibase.aist.go.jp/sdbs/)
112
-1
( )
113
-1
( )

: 2
: ,
:
C6H5CHO
C2H5OH
KCN ()
0,1 mol
25 mL
2 g 5 mL H2O
:
OH
O
2
C
H
KCN
!!!
!!!
-
-
( )!!!
!!!

. , 1
.
,
,2 95 30
. ,
.
- ,
.
.
:
: 137 .
...
IR
.
114
( ):
,
() (- ).
..
. ,
-
.
.
.
,
.
( = 8.7),
.
, .
115
, --
( )
. ()
--,
, --, .
.
,
.
116
1 ()

( ) . 1 (),
- ,
, (
).
.
-2

.

( ).
(+)
()
:
(1)
4-;
(2)
4 (3) 4--.
!
117
118
-1
( )
119
-1
( )
Oksidacija na benzoin do benzil
mehanizam na reakcija

( )
: 2
: ,
:
HNO3
0,025 mol
25 mL
:
OH
C C
O
HNO3
H O
C C
O
!!!
!!!

!!!
!!!

. , ,

1 (1/2 2 ).
.2
,
150 mL . ,

.
,

.3 ,
.
:
: 94-95 .
...
,
.
120
Oksidacija na benzoin do benzil
( ):

. =

.
:
121
Identifikacija na benzil
122
-1
( )
Sinteza na benzilna kiselina
postapka

: 3
: ,
:
KOH
C2H5OH
HCl
0,0143 mol
0,054 mol 6 mL H2O
10 mL
:
O
OH
KOH
-
" H C l"
OH
O
C
HO

! (
) ,
.
30

2

,
- KOH.
(10-15 min).
,
. ,
.1
,2
20-25 mL .
HCl
.
.
:
: 150-153 .
...

.
123
pra[awe
( ):
1,2-, .

-.
-
-.
124
pra[awe
(+)
1,3--1,3- ()
(1,2--1,2-)?
.
125
Identifikacija na benzilna kiselina
((http://riodb01.ibase.aist.go.jp/sdbs/))
126
-1
( )
Identifikacija na benzilna kiselina
127
Sinteza na acetilsalicilna kiselina
postapka

: 2
: ,
:

(CH3CO)2O
H2SO4
0,025 mol
0,063 mol
!!!
!
2

,
1 5 H2SO4.1.
15 min .
, , 5
mL .2 35
mL
.3
.
:
,
: 143 .
...

, .
128
(Fisher- )

(- )
( ).
- ,
( ).
:
1. - -
-
2. -
3.
4.
5.
2
3
.
- .
20
.
,
()
.
, .

(,
).
.
.
129
(-1)
(-1)
130
(-1)
Sinteza na benzoeva kiselina i benzil alkohol
postapka

Canizzaro-
: 3
: , ,
:
C6H5CHO
KOH
Na2SO4
5% NaOH
40% NaHSO3
. HCl
5 mL
5,5 g
30 mL
:
OH
O
2
C
H
!!!

2
5
206 !!!
!!!
K OH
C
H
O
H
C
+
OH
:
KOH 4 mL
.1
.
.
.
,

.
15
mL
. 2
.
1)
10 ml
NaHSO3,3 15 mL 5% NaOH.4
,
Na2SO4,
(40 )
(206 ).5
2)
. HCl. ,
.
:
: 122 .
...
IR .
131
pra[awa
( ) :
-
- .
, . -

( - )
.

-
(1)
(2).
- (-)

(-) .
(2).
, ( )
,
. (2),
.
-
- . ,
-
.
, .
132
pra[awa
:
(/) :
_________________________________________
@
__________________________________________
133
Identifikacija na benzoeva kiselina i benzil alkohol
(-1)
134
(-1)
Sinteza na anomeri na glukoza pentaacetat
postapki

: 3
: , ,
1:
D- ( )
(CH3CO)2O
bezvoden CH3COONa
2,5 g
12,5 mL
2g
2:
D- ( )
2,5 g
ZnCl2 (CH3CO)2O
0,5 g 14 mL
1:
.
.
(~1,5 ).
. , 50 .
. ( 130-132 ).
2:
2
. 2.
, 2-(3)2. ,
(~1 ) . ,
120 . .
. ( 109-111 )
...
,
.
135
Sinteza na anomeri na glukoza pentaacetat
:

. .

.
1: / ,
.
,
.
( )
.
2: /
(100)

. ( - )
- .
3: / Lewis-
(ZnCl2). Lewis-
.
136
Izolacija na eugenol
postapka
1. Fischer- D- (1-6)
2. Haworth-
.
3. - - .
4. -D- . .
5. ?
137
postapka

: 3
: , ,
:
Eugenia Caryophyllata
10 g
30 mL
:
OH
O C H3
C H2
CH
C H2
2--4-;
2--4-(2-)
:
,
~500 mL. 150 mL
(min 50 mL ).
.
Na2SO4. .

( = 253 ; = 1,06 g/cm3).
...
% / .
138
postapka
139
(-1)
Izolacija na kofein
postapka

: 3
: ,
:
Na2CO3
30 g
40 mL
8g
:
O
CH3
O
CH3
N
N
N
CH3
1,3,7-trimetilksantin
:
1000 mL ~250 mL ,
Na2CO31 .
. 10 min da vrie
.
2 .
. 2

Na2SO4.

.
,
.

. = 238
...
(1),
.
(m2 = + ).
%
.
140
Izolacija na kofein
postapka
141
(-1)
Sinteza na nepoznat produkt I
postapka
():

:
2.4 mL
0.9 mL
14 mL 96% EtOH
18 mL 1%
:
, .
- . 30 .
( ) .
.
. 110-111. IR
.
:
142
Sinteza na nepoznat produkt I
pra[awa i identifikacija
.
? ( !)
1 (http://riodb01.ibase.aist.go.jp/sdbs/)
143
(-1)
Sinteza na nepoznat produkt II
pra[awa
(): -

:
0.0183 (3--1-)
0.0233
.
:
!
1.
3 24
2. .
3. 5
4. 8
5.
.
6. , :
1) 6 mL - 23. .

2) 6 mL - NaCl. .

3) Na2SO4 (10 min)
7. ( 142 , IR )
144
pra[awa
:
1.
.
2. _____________________________
3. :
-
_____________________________
- 23 - ________________________________________________
Na2SO4 _____________________________________________
3. ?
145
identifikacija
2 (http://riodb01.ibase.aist.go.jp/sdbs/)
146
(-1)
Sinteza na nepoznat produkt III
postapka
():
:
0,5 mL 85%
0,5 mL
:
0,5 mL 85% 2,5 mL ,
.
. .
. . 107 .
:
147
PRILOG

IR
IR
(0-100:)
148
Presmetuvawe na prinos
PRILOG

.
100.
10 0
. 1- 1-
74.12 /
= 0.8098/
137.08 /
:
17 mL 1-,
20 mL .
24 ,
16,2 1-.

.
,
1- ( ).

.
1-
( ).

1 .
(1-) = 0,8098 / x 17 = 13,77 1-
(1-) = 13,77 / 74,12 / = 0,1857 1-
1 1- 1 1- 1 0,1857 () = 0,1857 x 137,08 / = 25,44 .
.
149
Presmetuvawe na prinos
PRILOG
(/
) %.
16.2 g
100 63.7%
25.44 g
,
. 50-80%
, 80 . 100%
.
150
Vodewe na laboratoriski dnevnik i Laboratoriski izve[taj
PRILOG

.

.
:

( )

.

.
. .

. , ,
( , , .),
.
( )
( ).
.
,
.
.
(%).
.
151
Laboratoriski izve[taj
() /
() / ()
152
(/3)
( , ,
. )
( ):
:
153
.
154
PRILOG
Organski rastvoruva~i
155
PRILOG
Fizi~ki konstanti na naj~esto koristeni organski rastvoruva~i
(760
)
()
()
( )
1,049
1,3716
6,2
10
20
-1
()

117,9
16,6
56,2
-95,3
-30
0,79
1,3588
20,7
1000
81,6
-45,2
0,786
1,3442
37,5
40
**
80,1
5,5
-11
0,874
1,5011
2,3
1-
(- )
117,3
-89,5
35
0,81
1,3993
17,5
100
2-
(- )
99,5
-114,7
26
0,808
1,3978
16,6
100
76,5
-22,9
1,594
1,4601
2,2
10
61,7
-63,5
1,483
1,446
4,8
10
80,7
6,6
-18
0,779
1,4266
300
1,2-
( )
83,5
-35,4
15
1,235
1,4448
10,4
20
39,8
-95,1
1,327
1,4242
8,9
200
( )
156
PRILOG
( )
(760
)
()
()
( )
400
20
-1
()

34,5
-116,2
-40
0,714
1,3526
4,3
83
-58
0,863
1,3796
7,2
, -
157
-60,5
57
0,949
1,4305
36,7
189
18,5
95
1,101
1,477
46,7
1,4-
101,3
11,8
12
1,034
1,4224
2,2
50
( )
78,5
-117,3
0,789
1,3611
24,6
1000
77,1
-83,6
-3
0,9000
1,3723
400
69
-95
-23
0,66
1,3751
1,9
100
( )
65
-93,3
11
0,791
1,3288
32,7
200
2--2-
( - )
82,2
25,5
0,789
1,3878
12,7
100
36,1
-129,7
-49
0,626
1,3575
1,8
600
( )
157
20
PRILOG
(760
)
()
()
( )
20
-1
()
1-
( - )
97,4
-126,5
15
0,804
1,385
20,3
200
2-
( )
82,4
-89,5
22
0,786
1,3776
19,9
400
115,5
-41,6
20
0,982
1,5095
12,4
67
-108,6
-17
0,889
1,405
7,6
200
110,6
-95
0,867
1,4961
2,4
200
()
138144
<-45
~25
~0,87
~1,50
2,4
200
= : 8
. !
*
.
, .
158
IR
(IR)
IR
159
IR
IR
cm
36403610 (s, sh)
OH ,

35003200 (s,b)
OH , H
34003250 (m)
NH
, ,
33002500 (m)
OH
C( )CH: CH
()
31003000 (s)
CH
31003000 (m)
=CH
30002850 (m)
CH
28302695 (m)
HC=O: CH
22602210 (v)
C( )N
22602100 (w)
C( )C
17601665 (s
C=O
()
17601690 (s)
C=O
17501735 (s)
C=O
17401720 (s)
C=O
17301715 (s)
C=O
1715 (s)
C=O
17101665 (s)
C=O
, ,
16801640 (m)
C=C
16501580 (m)
NH
16001585 (m)
CC (inring)
15501475 (s)
NO
15001400 (m)
CC (inring)
14701450 (m)
CH
33303270 (n, s)
160
IR
13701350 (m)
CH rock
13601290 (m)
NO
13351250 (s)
CN
13201000 (s)
CO
, ,
,
13001150 (m)
CH wag (CH2X)
13001150 (m)
CH wag (CH2X)
12501020 (m)
CN
1000650 (s)
=CH
950910 (m)
OH
NH wag
900675 (s)
CH "oop"
850550 (m)
CCl
725720 (m)
CH rock
700610 (b, s)
C( )CH: CH
690515 (m)
CBr
910665 (s, b)
m=medium, w=weak, s=strong, n=narrow, b=broad, sh=sharp
161
IR
IR
.
-1
C-H 30002850 cm
-1
C-H 1470-1450 cm
-1
C-H , 1370-1350 cm
-1
C-H , , 725-720 cm
.
-1
C=C 1680-1640 cm
-1
= C-H 3100-3000 cm
-1
= C-H 1000-650 cm
.
-1
CC 2260-2100 cm
-1
CC H: C-H 3330-3270 cm
-1
CC H: C-H 700-610 cm
.
-1
C-H 3100-3000 cm
-1
-, , 2000-1665 cm
-1
C C- (-) 1600-1585 cm
-1
C C (-) 1500-1400 cm
-1
C p 900-675 cm
.
-1
H , 3500-3200 cm
-1
CH 1260-1050 cm ()
.
C= :
-1
o 1715 cm
-1
o , - 1685-1666 cm
.
-1
C-H = 2830-2695 cm
C= :
-1
o 1740-1720 cm
-1
o , - 1710-1685 cm

.
-1
H 3300-2500 cm
-1
C = 1760-1690 cm
-1
C- 1320-1210 cm
-1
H 1440-1395 950-910 cm
.
C=
-1
o 1750-1735 cm
-1
o , - 1730-1715 cm
-1
C- 1300-1000 cm
.
-1
NH 3400-3250 cm
-1
o 1 : 2 : 3400-3300 3330-3250 cm
-1
o 2 : 1 3350-3310 cm
o 3 : -1
N-H ( 1 ) 1650-1580 cm
-1
C-H ( ) 1335-1250 cm
-1
C-H ( ) 12501020 cm
-1
N-H w ( 1 2 ) 910-665 cm

-1
1550-1475 cm
-1
1360-1290 cm
162
IR
( )
( )
163
IR
1- ( )
-1
-1
3000 cm 1400-1600 cm .
-1
1800 cm (overtone-).
( )
164
IR
1720 cm
2- ( CCl4)
-1
3000 cm
3- ( )
-1
3- ( CCl4)
165
IR
-1
1700 cm W 2800 cm
( CCl4)
-1
166
IR
( CCl4)
-1
2200 cm .
-1
-1
2200 cm 3300 cm
1- ( )
167
IR
2- ( )
( CCl4)
-1
-1
: (1760-1690 cm ) (3300-2500 cm )
168
IR
( )
( CCl4)
169
IR
: (1750-1735 cm 1730-1715 cm - - ) C-O
-1
1320-1000 cm )
-1
-1
( CCl4)
( CCl4)
170
IR
-1
3300-3500 .
. .
( CCl4)
( )
171
IR
( CCl4)
:
(Nujoll)
172
(0-100:)
0-100
(C)
0.0
5.0
10.0
12.5
15.0
15.5
16.0
16.5
17.0
17.5
18.0
18.5
19.9
(mmHg)
4.6
6.5
9.2
10.9
12.8
13.2
13.6
14.1
14.5
15.0
15.5
16.0
16.5
(C)
(mmHg)
(C)
19.5
20.0
20.5
21.0
21.5
22.0
22.5
23.0
23.5
24.0
24.5
25.0
26.0
17.0
17.5
18.1
18.6
19.2
19.8
20.4
21.1
21.7
22.4
23.1
23.8
25.2
27.0
28.0
29.0
30.0
35.0
40.0
50.0
60.0
70.0
80.0
90.0
95.0
100.0
(mmHg)
26.7
28.3
30.0
31.8
42.2
55.3
92.5
149.4
233.7
355.1
525.8
633.9
760.0
173
:
Bell E.C. Douglass F.T. Clark K.A. Organic chemistry laboratory, with standard and microscale experiments, 3e,
Harcourt College Publishers, 2001 (prevod od angliski Bogdanov J. i Bogdanov B.)
Davis G.B. Fairbanks J. A. Carbohydrate chemistry, Oxford Chemistry Primers, Oxford University Press, 2002
Harwood M. L, Moody J. C Experimental organic chemistry,principles and practice, Blackwell Science, 1989
Keese R, Brndle MP, Toube T. P, Practical organic synthesis, A students guide, Wiley, 2007
Lazarevi} M. Petrova D., Praktikum po organska hemija, Univerzitet Sv. Kiril i Metodij, Skopje, 1993
Lindhorst K. T. Essentials of carbohydrate chemistry and biochemistry 3e, Wiley-VCH, 2007
Milic B.Lj. ilas J.M. anadanovic Brunet J.M , Eksperimentalna organska hemija, Univerzitet u Novom Sadu,
Tehnoloski Fakultet, 1996
Zubrick W.J. The organic chem lab survival manual, 7e, Wiley, 2008
SDBSWeb : http://riodb01.ibase.aist.go.jp/sdbs/ (National Institute of Advanced Industrial Science and
Technology, 2010)
174
Katedra za organska Hemija

Farmacevtski Fakultet
Katedra za Organska hemija 2010
Univerzitet Sv. Kiril i Metodij -Skopje

Практикум органска хемија

Uploaded by

Document Information

Copyright

Available Formats

Share this document

Share or Embed Document

Sharing Options

Did you find this document useful?

Is this content inappropriate?

Copyright:

Available Formats

Практикум органска хемија

Uploaded by

Copyright:

Available Formats

Farmacevtski fakultet

(CANCER SUSPECTED AGENTS)

6,0 g 100 mL = 7,5 g X

% = mpo / mpred x 100

0.8g/100ml 0 5g/100ml 78.

20% NaOH __________ ml

25% HCl ___________ ml

760 mmHg 200 ,

0,448 mol / 1 mol ,

RCO2NH4 + 3 NH3 + H2O + Ag

Slika 1. Elektromagneten spektar

DEFORMACIONI VIBRACII (VO RAMNINA)

DEFORMACIONI VIBRACII (NADVOR OD RAMNINA)

- (Neat) (CCl4, CHCl3, CH2Cl2)

1600, 1580, 1500

N CH3 CH3 CH2 C O H

Csp3 - Csp3 ___________, Csp2- Csp2 ___________, Csp Csp____________

H-- Csp3___________, HCsp2___________, H-- Csp___________,

Csp3 - Osp3 ___________, Csp3 Osp2___________,

2. SpartanView (folderite): Chapter3 -> Molecule >Problem 3. (a,b,c) .

Newman- (1-2 3-2)

diedralen agol () (pome|u

Oksidacija na benzoin do benzil

Oksidacija na benzoin do benzil

Sinteza na benzilna kiselina

Sinteza na benzilna kiselina

Sinteza na benzilna kiselina

Identifikacija na benzilna kiselina

Identifikacija na benzilna kiselina

Sinteza na acetilsalicilna kiselina

Sinteza na acetilsalicilna kiselina

Sinteza na acetilsalicilna kiselina

Sinteza na benzoeva kiselina i benzil alkohol

Sinteza na benzoeva kiselina i benzil alkohol

Sinteza na benzoeva kiselina i benzil alkohol

Identifikacija na benzoeva kiselina i benzil alkohol

Sinteza na anomeri na glukoza pentaacetat

Sinteza na anomeri na glukoza pentaacetat

Sinteza na nepoznat produkt I

Sinteza na nepoznat produkt I

Sinteza na nepoznat produkt II

Sinteza na nepoznat produkt II

Sinteza na nepoznat produkt II

Sinteza na nepoznat produkt III

Vodewe na laboratoriski dnevnik i Laboratoriski izve[taj

Fizi~ki konstanti na naj~esto koristeni organski rastvoruva~i

Fizi~ki konstanti na naj~esto koristeni organski rastvoruva~i

Fizi~ki konstanti na naj~esto koristeni organski rastvoruva~i

36403610 (s, sh)

m=medium, w=weak, s=strong, n=narrow, b=broad, sh=sharp

Katedra za organska Hemija

You might also like

Csp3 - Csp3 _____, Csp2- Csp2 _, Csp Csp________

H-- Csp3_____, HCsp2_, H-- Csp_______,

Csp3 - Osp3 _, Csp3 Osp2_,