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7/25/2019 Key Final Exam 2040 1516
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45
1
^6 ^^ ^ k.m^ l ^^s
>e
.P
^r
^oH c
Providethemajor organi c p roduct s)for thefol low ing reactions. Drawthe
sothat stereochemistry isobviousandindicateifenantiomersareformed.
enantiomer formationand thereisnone,you
will
notreceive
full
credit.
carbonsas well,you
w i l l
notreceiveanycredit i f your carbon countis o
structure
is
not correct.
0
II
H2Cr04 H2O ^ ^ C
7/25/2019 Key Final Exam 2040 1516
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7/25/2019 Key Final Exam 2040 1516
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2.
C H ; , C H 2 C H 2 B r
(2
p r o d u c t s )
P r o v i d e l U P A C names for the fo llo wing co mpo und, s p ecifying s tereochem
necessary . )
P r o v i d e t h e s t r u c t u r e o f t h e c o m p o u n d c o r r e s p o n d i n g t o t he f o l l o w i n g c
name.
Ethylene glycol
1^0 ol-l
Houi
m(xny
i f^^s
did
1
ioJk aLttx
cohAt^orJ mamas
7/25/2019 Key Final Exam 2040 1516
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T r i c h l o r i n A is a natural product w i t h si gnifi cant toxi ci ty against breast
ome steps
i n apartial synthesis are shown below.
a m o n o anion a dianion
(pull o ff most acidic proton)
1. E H O H
uivalent
H- CHjCCH^)/
y^
3 ^ > D
l i ^ ^ ^
/
CH2
a. Cir cl e the tw o most acidic proton s i n the starting mater ial .
b. Provi de thereagents A, C, E and the interm ediates B and D.
C: ^ ^ ^
E:
c. The diani on Breacts specifical ly at one of
its
nucl eophi lic sites.
n u c l e o p h i l i csites on the diani on and EX PE AI N wh y the reaction is so
fo r
one site. ,
^ li
7/25/2019 Key Final Exam 2040 1516
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20
4
Compare the followingsets o f reactions and circle the one that
will
be fast
reason for yourchoice. NO TE : I f you do not provide the correct reason, or
w i l l notreceive full credit for your selection. These are like problems we
a.
A. C H 3 C H 2 C H 2 B r + N a X W
-oMsrr
C H 3 C H 2 C H 2 C N + Na'Br-
2.
C H 3 C H C H 3
+
N a A N -
Br
DMSO
C H 3 C H C H 3
+
Na ' Br -
C N
^
Reason:
S Q ' ^ S oA)^'^^a./^ f
ClS^^ ^
b.
1.
C H 3 C H 2 C H 2 Br
+
C H s O N a *
H2O
CH3CH2CH2OCH3
+
Na^Bf
2. C H 3 C H 2 C H 2 Br + CH3SNa*
Rea^om-
5. Problem 11-55c.
Propose
an arrow pushing mechanism for the fol low in g reaction. Hint: the thi
pinacol rearrangement product. 7 /)c5^ uuC^rc ^10 / tfClprCSSK/lf
o
7/25/2019 Key Final Exam 2040 1516
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Ethylene oxid e oxira ne) is a valuable building block for organic synthe
carbon of its two carbon skeleton has a func tion al group . The key to rec
structural
unit
derived
from
ethylene oxide is the
presence
o f Nu -CHj-CH^
The fol low ing is aseries of reactions startingwith ethylene oxide.
Ple
necessary
reagents
A-F , for
each
conversion.
H , C N
\
H
O H
O H
B
H 3 C N
V
D
B:
IX
O H
O H
H 3 C N
\
H3 C N O
H 3 C N S
C:
D :
E:
dec
F:
7/25/2019 Key Final Exam 2040 1516
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24
7 Provide syntheses of the fo ll ow in g compounds using the starting materi
othernecessary inorganic and organic reagents. Be sure to show a ll pert
compounds and you w i l l
receive
credit for them . This is not a mechanism
arrow-p ushing . I f you do not kno w the structure of
cyclohexene
or
a
may ask for them but w i l l
lose
points. WO RK BACKWARDS
a.
H int:
the last
step
is an oxidation.
Cyclohexene
^ [
7/25/2019 Key Final Exam 2040 1516
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/
24
8. Man y organic reactions can be broadl y classified asacid base reactions,
electrophile/nucleophile. It is very important do be able to recognize th
in molecules as well as comparative acidities.
A l l
of the compounds below can react as acids.
C i
1 2 3 4
X^
a. C ircle the most acidic proton oneachcompound.
b.
Without
u sing a table, ra nk ^ h e compounds i n order o f increasing ac
the
left).
c. The fo ll ow in g reaction is kn own to occur:
O H + PB n
B r
Identify the Nuc leop hil ic Nu) and Electr ophi lic E) sites in the startin
e a ,
of
g p
r