Rozwiązania zadań z kolokwium 2 (z dn. 08.05.2008) Zadanie 1.
C C6H5
HO CH2CH3 C H
C6H5
CH3CH2 OH H C CH2C6H5
CH3 Br H
H2O , T
C CH2C6H5
CH3 H
Br C
C6H5
OH2 CH3CH2
H C
C6H5
H2O
CH2CH3
+
H H2OC C6H5
CH2CH3 H
- H
+ a)
:
(CH3)2CHC O
CH3+ OH H2O + (CH3)2CHC O
CH2 (CH3)2CHC CH2
.. : :
O: ..
b)
:
(CH3)2CHC O
CH2 C C6H4 Br p O
H
: : .. :
H2O
:
(CH3)2CHC O
CH2
: ..
+ C C6H4 Br O
H
p
..
(CH3)2CHC O
CH C OH
H C6H4 H
Br-p + OH
+
: .. : : :
: : :
(CH3)2CHC O
CH CH C6H4 Br-p + H2O + OH
: ..
(CH3)2CHC O
CH CH OH
C6H4 Br-p
.. :
c)
CH3 H H
Cl
C2H5ONa
CH3 Cl
H
C2H5
..
O H..
CH3 - H2O, - Cl
C2H5OH
Zadanie 2.
NO2
F F
CH3ONa (nadmiar)
T
NO2
OCH3
F
+ NaF A: 2-fluoro-1-metoksy-4-nitrobenzen (lub 3-fluoro-4-metoksynitrobenzen)
a)
b)
CH3CH2C OOCH3 CH3CH2CCH3 CH3 OH
+ CH3OH B: 2-metylobutan-2-ol
C: metanol H3O
2)
1) CH3MgI (nadmiar)
1
C O
CH3 1) 3 Br2 , NaOHaq 2) H3O
C O
OH+ CHBr3
D: kwas benzoesowy E: bromoform
c)
I CH2CH2CH2CH2Br CH3COONa
DMF I CH2CH2CH2CH2OCCH3 O
+ NaBr
d)
F
C CH3
HO C3H7
H
PBr3
C CH3
C3H7 Br H
G: (S)-pentan-2-ol (R)-2-bromopentan
e)
H3C C CH2CH3
f)
OBr2 , H
H3C C CHCH3
O Br
H: keton 1-bromoetylowo-(p-metylofenylowy)
Br C
O
H
+
H C OH
1) NaOHstęż.
2) H3O Br CH2OH
+
H C OOH I: alkohol p-bromobenzylowy J: kwas mrówkowy
g)
NO2
Br
+ [(CH3)2CHCH2]2CuI
NO2
CH2CH(CH3)2 L: m-bromonitrobenzen L: (2-metylopropylo)nitrobenzen
h)
(CH3)2CHCH2Br + 2 Li
(
CH3)2CHCH2Li + LiBr 2 (CH3)2CHCH2Br + CuI [(CH3)2CHCH2]2CuI + LiIK
C CH3
HO C2H5
H C
CH3
C2H5 CN H
i)
C CH3
TsO C2H5 H TsCl
pirydyna
M
NaCN DMSO
N TsCl = p-C6H4SO2Cl (chlorek kwasu p-toluenosulfonowego)
2
(CH3)2C=CH2 CH3COOOH
(CH3)2C CH2
O C2H5OH, H
(CH3)2C CH2OH OC2H5
P: 2-etoksy-2-metylopropan-1-ol
j)
OH
H3C CH3CH2COCl H3C OCCH2CH3 O
pirydyna
AlCl3, T H3C
C O
CH2CH3
k)
OHR S: keton etylowo-(2-hydroksy-5-metylofenylowy)
l)
CH3CH2CH CH2 Br2, H2OCH3CH2CHCH2Br OH
T: 1-bromobutan-2-ol
NaOH (1 mol)
CH3CH2HC CH2
O
U 2) H3O 1) CH3CH2ONa
CH3CH2CHCH2OCH2CH3
OH
W: 1-etoksybutan-2ol
Zadanie 3.
a)
CH3CH2CH2OH PCC CH3CH2C O H 2 CH3CH2CO H
CH3CH2CH C CH3
C O H
LiAlH4 CH3CH2CH CCH2OH CH3
NaOHaq , T - H2O
b)
CH3
H2SO4stęż.
T
CH3
SO3H
NaOH (stapianie)
T
CH3
ONa CH3CH CH2 HBr / (RO)2
CH3CH2CH2Br
CH3
OCH2CH2CH3 - NaBr
CH3CH2CH CH2 HBr
(RO)2 CH3CH2CH2CH2Br P(C6H5)3
[CH3CH2CH2CH2 P(C6H5)3] Br BuLi 1) H3O
2) KMnO4aq T CH3CH2C O CH3
CH3CH2CH2CH P(C6H5)3
CH3CH2C O
CH3
+
CHCH2CH2CH3P(C6H5)3
- O=P(C6H5)3
CH3CH2C CHCH2CH2CH3 CH3
d)
2 PBr3 1) O3
2) H2O/Zn C C CH2
CH2 H2C
O H O
H
1) 2 CH3MgI
2) H3O+ C C CH2
CH2 H2C
CH3 CH3
OH
HO C C
CH2
CH2 H2C
CH3 CH3
Br Br
c)
3
Zadanie 4.
a)
OH ONaOCH3
OCH3
+
ONa OH
OCH3 OCH3
+
CH3 C CH3
CH3
OH
+
KOHaq reakcja nie zachodzib)
c)
C6H5 Li +CHO
OH CHO
OLi
+
C6H6d)
C6H5ONa + CH3CH2CHCH3OH
reakcja nie zachodzi
C CH3
C3H7 OH
e)
C6H5CH2MgCl + H C CH3OMgCl C3H7
H + C6H5CH3
H3C OH
