Chemical Pathways and Reactions
The Scrambled Full Monty
Help
meh !
•
Provide examples of three different pathways leading to cyclo
compounds
a
)
e
t
h
e
n
e
+
C
H
2
I
2
-
-
-
-
-
-
b)
ethene +CHCl
3
--------
dichlorocarbene
insertion
Simmons-Smith
insertion
Zn(Cu)
OH
-
Diazomethane
insertion
c)
ethene + CH
2
N
2
-----------
+ N
2
light
??????
Cl
2
/Wet CCl
4
??????
HCl in acetic acid
w/HOOH
??????
B
2
H
6
neat
or in ether
All anti-mark, 90% yield
3 min,Brown 2 step
ozonolysis
Scrambled Exercise : (CONTINUED)
?????
CHCl
3
/OH-
dichlorocarbene
insertion
?????
Scrambled Exercise 2: (CONTINUED)
C
H
2
I
2
Z
n
(
C
u
)
Simmons-Smith insertion
HCl in acetic acid,
no HOOH
?????
Rxn name ???
•
There are two alternative routes to make anti- versions
of 1,2-dihydroxyethane (diols) from ethene. What are
they ?
Exercise 2: (CONTINUED)
Formic acid/peroxide
ethene
wet CCl
4
OH
-
H
+
ethene +Br
2
a)
b)
?????
CCl
4
/HOOH light
There are two different choices of reagents leading to syn-
versions of 1,2-dihydroxyethane from ethene. What are they ?
a)
b)
Scrambled Exercise 2: (CONTINUED)
KMnO
4
(cold)
OsO
4
in ether
?????
NaBH
4
in KOH
W
h
a
t
i
s
t
h
e
i
n
d
u
s
t
r
i
a
l
r
o
u
t
e
f
o
r
c
o
n
v
e
r
t
i
n
g
e
t
h
e
n
e
t
o
e
t
h
a
n
o
l
?
C
o
n
c
H
2
S
O
4
H
2
O
E
t
h
e
n
e
-
-
-
-
-
-
-
-
-
-
-
-
e
t
h
y
l
s
u
l
f
o
n
a
t
e
-
-
-
-
e
t
h
a
n
o
l
+
H
2
S
O
4
What alkene originally was present if the
final product of ozonolysis is:
Scrambled Exercise 2: (CONTINUED)
??????
H
2
at 1 atm
25
o
C over Pt, Pd
or Ni
a)
n
???
…
…
???
b)
n
…
…
One more ….polymerization patterns
•
Predict the polymers formed by reacting:
a)
n
???
One more ….polymerization patterns
…
…
Make him stop !
Delve into various chemical reactions and pathways, including cyclo compounds formation, diol synthesis from ethene, ozonolysis products, and industrial routes for ethanol synthesis. Uncover the diverse reagents and conditions leading to specific product formations in organic chemistry.
Uploaded on Mar 09, 2025 | 0 Views
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Presentation Transcript
The Scrambled Full Monty Help meh !
Provide examples of three different pathways leading to cyclo compounds Zn(Cu) Simmons-Smith insertion ethene + CH2I2 ------ a) OH- Cl Cl b) ethene +CHCl3-------- dichlorocarbene insertion light c) ethene + CH2N2 ----------- + N2 Diazomethane insertion Cl2 /Wet CCl4 ?????? H O Cl
Scrambled Exercise : (CONTINUED) HCl in acetic acid w/HOOH ?????? Cl B2H6 neat or in ether H H2O2 OH OH- ?????? All anti-mark, 90% yield 3 min,Brown 2 step Zn/H+ O3 neat H + ozonolysis O O H
Scrambled Exercise 2: (CONTINUED) CHCl3/OH- Cl Cl ????? dichlorocarbene insertion CH2I2 Zn(Cu) ????? Simmons-Smith insertion Rxn name ??? HCl in acetic acid, no HOOH ????? Cl
Exercise 2: (CONTINUED) There are two alternative routes to make anti- versions of 1,2-dihydroxyethane (diols) from ethene. What are they ? Formic acid/peroxide ethene wet CCl4 OH- H+ ethene +Br2 b) OH a) H O CCl4/HOOH light Cl ????? Cl Cl Cl
Scrambled Exercise 2: (CONTINUED) There are two different choices of reagents leading to syn- versions of 1,2-dihydroxyethane from ethene. What are they ? a) KMnO4 (cold) H O OH b) OsO4 in ether NaBH4 in KOH H Hg(OAc)2 OH THF ????? What is the industrial route for converting ethene to ethanol? Conc H2SO4 H2O Ethene ------------ ethyl sulfonate---- ethanol + H2SO4
Scrambled Exercise 2: (CONTINUED) What alkene originally was present if the final product of ozonolysis is: O O H2 at 1 atm 25oC over Pt, Pd or Ni ??????
One more .polymerization patterns HO-OH/light a) n b) ??? HO-OH/light n ???
One more .polymerization patterns Predict the polymers formed by reacting: a) n HO-OH/light ???
