ORGANIC CHEMISTRY,SOLNS...-ETEXT+BOX
4th Edition
ISBN: 9781119760634
Author: Klein
Publisher: WILEY
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Chapter 6.9, Problem 14ATS
Interpretation Introduction
Interpretation: The arrow pushing pattern for the given mechanism is to be interpreted for the conversion of compound 1 to 2.
Concept introduction: In a
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The compound below was exposed to a palladium catalyst to produce a macrocycle (large ring). The macrocycle subsequently
underwent a rearrangement to produce a fused hexacyclic (six-ring) structure. The ring system of the final product is one that is found
in a number of polycyclic natural products. Draw the initial product of the palladium-catalyzed reaction, the final product, and a
mechanism consistent with the rearrangement step.
Include stereochemistry in your answer.
SnBu,
TIO
Integrated Problem 23.67a
* Your answer is incorrect.
Draw the initial product of the palladium-catalyzed reaction:
Synthesize the product from the given material. Give the reagents necessary and draw out any intermediate products along the way.
Under acid-catalyzed conditions, epoxides can be opened by a variety of nucleophiles other than water, such as alcohols. In such a
case, the nucleophile will generally attack at the more substituted position. Using this information, predict the products for each
of the following reactions (a-b):
?
1) RCO-H
2) [H₂SOJ
Modify the given structure to draw the major product(s). Use the single bond tool to interconvert between double and single
bonds. If a racemic mixture of enantiomers is expected, draw both enantiomers. Note: you can select a structure and use Copy and
Paste to save drawing time.
CH₂
Edit Drawing
A
Chapter 6 Solutions
ORGANIC CHEMISTRY,SOLNS...-ETEXT+BOX
Ch. 6.1 - Prob. 1LTSCh. 6.1 - Prob. 1PTSCh. 6.1 - Prob. 2ATSCh. 6.2 - Prob. 3CCCh. 6.3 - Prob. 4CCCh. 6.3 - Prob. 5CCCh. 6.4 - Prob. 6CCCh. 6.6 - Prob. 7CCCh. 6.7 - Prob. 2LTSCh. 6.7 - Prob. 8PTS
Ch. 6.7 - Prob. 9PTSCh. 6.7 - Prob. 10ATSCh. 6.8 - Prob. 3LTSCh. 6.8 - Prob. 11PTSCh. 6.8 - Prob. 12ATSCh. 6.9 - Prob. 4LTSCh. 6.9 - Prob. 13PTSCh. 6.9 - Prob. 14ATSCh. 6.10 - Prob. 5LTSCh. 6.10 - Prob. 15PTSCh. 6.10 - Prob. 16ATSCh. 6.11 - Prob. 6LTSCh. 6.11 - Prob. 17PTSCh. 6.11 - Prob. 18ATSCh. 6 - Prob. 19PPCh. 6 - Prob. 20PPCh. 6 - Prob. 21PPCh. 6 - Prob. 22PPCh. 6 - Prob. 24PPCh. 6 - Prob. 25PPCh. 6 - Prob. 26PPCh. 6 - Prob. 27PPCh. 6 - Prob. 28PPCh. 6 - Prob. 29PPCh. 6 - Prob. 30PPCh. 6 - Prob. 31PPCh. 6 - Prob. 32PPCh. 6 - Prob. 33PPCh. 6 - Prob. 34PPCh. 6 - Prob. 35PPCh. 6 - Prob. 36PPCh. 6 - Prob. 37PPCh. 6 - Prob. 38PPCh. 6 - Prob. 39PPCh. 6 - Prob. 40PPCh. 6 - Prob. 41PPCh. 6 - Prob. 43ASPCh. 6 - Prob. 44ASPCh. 6 - Prob. 45ASPCh. 6 - Prob. 46ASPCh. 6 - Prob. 47ASPCh. 6 - Prob. 48ASPCh. 6 - Prob. 49ASPCh. 6 - Prob. 50IPCh. 6 - Prob. 51IPCh. 6 - Prob. 52IPCh. 6 - Prob. 53IPCh. 6 - Prob. 54IPCh. 6 - Prob. 55IPCh. 6 - Prob. 56IPCh. 6 - Prob. 57IPCh. 6 - Prob. 58IPCh. 6 - Prob. 59IPCh. 6 - Prob. 60IPCh. 6 - Prob. 61IPCh. 6 - Prob. 62CPCh. 6 - Prob. 64CP
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