EP INTRODUCTORY CHEM.-MOD.MASTERINGCHEM
8th Edition
ISBN: 9780134554433
Author: CORWIN
Publisher: PEARSON CO
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Chapter 12, Problem 59E
Interpretation Introduction
Interpretation:
The electron dot formula for
Concept introduction:
The electron dot formula shows the valence electrons which form the bond between the atoms in a molecule. The electron pairs that are shared by the atoms are known as bonding electrons. The other electrons that are present in order to complete the octet are known as non-bonding electrons. The electron dot formula is also known as the Lewis structure.
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19.84 Using your reaction roadmaps as a guide, show how to convert 2-oxepanone and ethanol
into 1-cyclopentenecarbaldehyde. You must use 2-oxepanone as the source of all carbon
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the way.
&
+ EtOH
H
2-Oxepanone
1-Cyclopentenecarbaldehyde
R₂
R₁
R₁
a
R
Rg
Nu
R₂
Rg
R₁
R
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R3
R
R
Nu enolate forming
R₁ R
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species or amines
Cyclic B-Ketoester
R₁₁
HOB
R
R₁B
R
R₁₂
B-Hydroxy carbonyl
R
diester
R2 R3
R₁
RB
OR
R₂ 0
aB-Unsaturated carbonyl
NaOR
Aldol
HOR
reaction
1) LDA
2) R-X
3) H₂O/H₂O
ketone,
aldehyde
1) 2°-amine
2) acid chloride
3) H₂O'/H₂O
0
O
R₁
R₁
R
R₁
R₁₂
Alkylated a-carbon
R₁
H.C
R₁
H.C
Alkylated methyl ketone
acetoacetic
ester
B-Ketoester
ester
R₁
HO
R₂ R
B-Dicarbonyl
HO
Alkylated carboxylic acid
malonic ester
Write the reagents required to bring about each reaction next to the arrows shown.
Next, record any regiochemistry or stereochemistry considerations relevant to the
reaction. You should also record any key aspects of the mechanism, such as forma-
tion of an important intermediate, as a helpful reminder. You may want to keep
track of all reactions that make carbon-carbon bonds, because these help you build
large molecules from smaller fragments. This especially applies to the reactions in…
Provide the reasonable steps to achieve the following synthesis.
Chapter 12 Solutions
EP INTRODUCTORY CHEM.-MOD.MASTERINGCHEM
Ch. 12 - Prob. 1CECh. 12 - Prob. 2CECh. 12 - Prob. 3CECh. 12 - Prob. 4CECh. 12 - Prob. 5CECh. 12 - Prob. 6CECh. 12 - Prob. 7CECh. 12 - Prob. 8CECh. 12 - Prob. 9CECh. 12 - Prob. 10CE
Ch. 12 - Prob. 11CECh. 12 - Prob. 12CECh. 12 - Prob. 1KTCh. 12 - Prob. 2KTCh. 12 - Prob. 3KTCh. 12 - Prob. 4KTCh. 12 - Prob. 5KTCh. 12 - Prob. 6KTCh. 12 - Prob. 7KTCh. 12 - Prob. 8KTCh. 12 - Prob. 9KTCh. 12 - Prob. 10KTCh. 12 - Prob. 11KTCh. 12 - Prob. 12KTCh. 12 - Prob. 13KTCh. 12 - Prob. 14KTCh. 12 - Prob. 15KTCh. 12 - Prob. 16KTCh. 12 - Prob. 17KTCh. 12 - Prob. 18KTCh. 12 - Prob. 19KTCh. 12 - Prob. 20KTCh. 12 - Prob. 21KTCh. 12 - Prob. 22KTCh. 12 - Prob. 23KTCh. 12 - Prob. 24KTCh. 12 - Prob. 25KTCh. 12 - Prob. 26KTCh. 12 - Prob. 27KTCh. 12 - Prob. 28KTCh. 12 - Prob. 29KTCh. 12 - Prob. 1ECh. 12 - Prob. 2ECh. 12 - Prob. 3ECh. 12 - Prob. 4ECh. 12 - Prob. 5ECh. 12 - Prob. 6ECh. 12 - Prob. 7ECh. 12 - Prob. 8ECh. 12 - Prob. 9ECh. 12 - Prob. 10ECh. 12 - Prob. 11ECh. 12 - Prob. 12ECh. 12 - Prob. 13ECh. 12 - Prob. 14ECh. 12 - Prob. 15ECh. 12 - Prob. 16ECh. 12 - Prob. 17ECh. 12 - Prob. 18ECh. 12 - Prob. 19ECh. 12 - Prob. 20ECh. 12 - Prob. 21ECh. 12 - Prob. 22ECh. 12 - Prob. 23ECh. 12 - Prob. 24ECh. 12 - Prob. 25ECh. 12 - Prob. 26ECh. 12 - Prob. 27ECh. 12 - Prob. 28ECh. 12 - Prob. 29ECh. 12 - Prob. 30ECh. 12 - Prob. 31ECh. 12 - Prob. 32ECh. 12 - Prob. 33ECh. 12 - Prob. 34ECh. 12 - Prob. 35ECh. 12 - Prob. 36ECh. 12 - Prob. 37ECh. 12 - Prob. 38ECh. 12 - Prob. 39ECh. 12 - Prob. 40ECh. 12 - Prob. 41ECh. 12 - Prob. 42ECh. 12 - Prob. 43ECh. 12 - Prob. 44ECh. 12 - Prob. 45ECh. 12 - Prob. 46ECh. 12 - Prob. 47ECh. 12 - Prob. 48ECh. 12 - Prob. 49ECh. 12 - Prob. 50ECh. 12 - Prob. 51ECh. 12 - Prob. 52ECh. 12 - Prob. 53ECh. 12 - Prob. 54ECh. 12 - Prob. 55ECh. 12 - Prob. 56ECh. 12 - Prob. 57ECh. 12 - Prob. 58ECh. 12 - Prob. 59ECh. 12 - Prob. 60ECh. 12 - Prob. 61ECh. 12 - Prob. 62ECh. 12 - Prob. 63ECh. 12 - Prob. 64ECh. 12 - Prob. 65ECh. 12 - Prob. 66ECh. 12 - Prob. 67ECh. 12 - Prob. 68ECh. 12 - Prob. 69ECh. 12 - Prob. 70ECh. 12 - Prob. 71ECh. 12 - Prob. 72ECh. 12 - Prob. 73ECh. 12 - Prob. 74ECh. 12 - Prob. 75ECh. 12 - Prob. 76ECh. 12 - Prob. 77ECh. 12 - Prob. 78ECh. 12 - Prob. 79ECh. 12 - Prob. 80ECh. 12 - Prob. 81ECh. 12 - Prob. 82ECh. 12 - Prob. 83ECh. 12 - Prob. 84ECh. 12 - Prob. 85ECh. 12 - Prob. 86ECh. 12 - Prob. 87ECh. 12 - Prob. 88ECh. 12 - Prob. 89ECh. 12 - Prob. 90ECh. 12 - Prob. 91ECh. 12 - Prob. 92ECh. 12 - Prob. 93ECh. 12 - Prob. 94ECh. 12 - Prob. 95ECh. 12 - Prob. 96ECh. 12 - Prob. 97ECh. 12 - Prob. 98ECh. 12 - Prob. 99ECh. 12 - Prob. 100ECh. 12 - Prob. 1STCh. 12 - Prob. 2STCh. 12 - Prob. 3STCh. 12 - Prob. 4STCh. 12 - Prob. 5STCh. 12 - Prob. 6STCh. 12 - Prob. 7STCh. 12 - Prob. 8STCh. 12 - Prob. 9STCh. 12 - Prob. 10STCh. 12 - Prob. 11STCh. 12 - Prob. 12STCh. 12 - Prob. 13STCh. 12 - Prob. 14STCh. 12 - Prob. 15STCh. 12 - Prob. 16STCh. 12 - Prob. 17STCh. 12 - Prob. 18ST
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