Kolokwium I (grupa dodatkowa) z dnia 30.10.2008 – rozwiązania
ZADANIE 1
=
a) CH
3CH
2CH
2CH
3 Cl2h
CH3
C2H5 Cl H
CH3
C2H5 Cl
H
Cl-CH
2CH
2CH
2CH
3+
1-chlorobutan (R)-2-chlorobutan (S)-2-chlorobutan
A B C
A + B + C
kat. AlCl3
+
C6H5
C2H5
CH3 H
C6H5 C2H5 CH3
H
(S)-2-fenylobutan (R)-2-fenylobutan
D E
+
b) A : (B+C) = 6(H
1o)
.1 : 4(H
2o)
.3,8 = 6 : 15.2; B : C = 7,6 : 7,6 = 1 : 1
c) CH
3CH
2CH
2CH
2Cl
kat. AlCl3CH
3CHCHCH
2AlCl
4H
C2H5
CH3 H
C
6H
6E B
C
kat. AlCl3 kat. AlCl3
= E
E E
E H
E H
E H
E H
=
E H
E
D
C
6H
6ZADANIE 2
CH3CH2C(O)Cl AlCl3
C(O)CH2CH3
Zn, HClstez.
t
CH2CH2CH3
a)
Br2h
CHCH2CH3 Br
1
b)
CH3CH2CH CH2 Br2CH3CH2CH CH2
Br Br
2 NaNH2 CH3CH2C CH NaNH2
NH3 c CH3CH2C CNa
CH3CH2CH2CH2Br
CH3CH2C CCH2CH2CH2CH3 Na / NH3C
C C
CH2CH2CH3 H
H3CH2C
H CH3CH2CH CH2 HBr
ROOR CH3CH2CH2CH2Br
c)
H CH3CH3 H
+
t, pH3C
H3C
H2/Pd H3C
H3C
H3C H3C CH3
CH3
d)
CH3 Br2, Fe CH3Br
KMnO4 aq
t
CO2H Br
HNO3.
H2SO4
CO2H Br NO2
C C
H H
H3C CH3
e)
KMnO4 aq 0 OCO O
Mn
H3HC CHH3 O O
H2O HO OH
H3HC CHH3
CH3 OH H
OH H
CH3
ZADANIE 3
KMnO4 aq
t
CH2CH3 CH2CH3
CH2CH3 CH3CH2
CH3CH2C(O)CH2CO2H KMnO4 aq
t
A 1,2-dietylocykloheksa-1,4-dien B 1,4-dietylocykloheksa-1,4-dien
A B
A
1) O32) H2O/Zn CH3CH2C(O)CH2CHO 1) O3
2) H2O/Zn
B
+
t, pCH2CH3 CH2CH3 CH2CH3
CH2CH3
+
CH2CH3 CH2CH3
t, p
+ B
CH2CH3 CH2CH3
LUB
+
CH2CH3 CH3CH2
tylko A
2
ZADANIE 4
h
b)
a)
NBS, CCl4+ CCH
2CH=CHCH
2Br
3-bromopent-1-en 1-bromopent-2-en
CH
3CH=CHCH=CHCH
3 1 mol Cl2CH
3CHCHCH=CHCH
3+ CH
3CHCH=CHCHCH
3Cl Cl Cl Cl
4,5-dichloroheks-2-en 2,5-dichloroheks-3-en
d)
CH
3CH
2C CH
CH
3C CCH
3 2 mole HBrCH
3CBr
2CH
2CH
32,2-dibromobutan c)
1 mol HBrCH
3CH
2CBr CH
22-bromobut-1-en
e)
CH3 H3C
1) [BH3] 2) H2O2/OH-
CH3 CH3 H OH
CH3 H H3C
OH
+
f)
Br2, H2O Br Br +
OH2
H2O CH3
CH3
CH3
CH3 Br
OH2
+ Br
OH2 CH3
CH3 Br
OH
+ Br
OH CH3 -H
CH
3CH
2CH
2CH CH
2CH
3CH
2CHCH CH
2Br
