GENERAL ORGANIC+BIO...(LL)-W/MOD.ACCESS
3rd Edition
ISBN: 9780134466699
Author: FROST
Publisher: PEARSON
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Chapter 12, Problem 1IA.8Q
Summary Introduction
To determine:
Whether the metabolic reactions are the
Introduction:
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(racemic)
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
atoms in the target molecule. Show all reagents and all molecules synthesized along
the way.
&
+ EtOH
H
2-Oxepanone
1-Cyclopentenecarbaldehyde
R₂
R₁
R₁
a
R
Rg
Nu
R₂
Rg
R₁
R
R₁₂
R3
R
R
Nu enolate forming
R₁ R
B-Alkylated carbonyl
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
GENERAL ORGANIC+BIO...(LL)-W/MOD.ACCESS
Ch. 12 - Prob. 12.1PPCh. 12 - How can you identify an anabolic reaction?Ch. 12 - Prob. 12.3PPCh. 12 - Prob. 12.4PPCh. 12 - Prob. 12.5PPCh. 12 - Prob. 12.6PPCh. 12 - Prob. 12.7PPCh. 12 - Prob. 12.8PPCh. 12 - Prob. 12.9PPCh. 12 - Prob. 12.10PP
Ch. 12 - Prob. 12.11PPCh. 12 - Prob. 12.12PPCh. 12 - Name a carbohydrate (if any) that undergoes...Ch. 12 - Prob. 12.14PPCh. 12 - Prob. 12.15PPCh. 12 - Prob. 12.16PPCh. 12 - Prob. 12.17PPCh. 12 - Prob. 12.18PPCh. 12 - Prob. 12.19PPCh. 12 - Prob. 12.20PPCh. 12 - Prob. 12.21PPCh. 12 - Prob. 12.22PPCh. 12 - Prob. 12.23PPCh. 12 - Prob. 12.24PPCh. 12 - Prob. 12.25PPCh. 12 - Prob. 12.26PPCh. 12 - Prob. 12.27PPCh. 12 - Prob. 12.28PPCh. 12 - Prob. 12.29PPCh. 12 - Prob. 12.30PPCh. 12 - Prob. 12.31PPCh. 12 - Prob. 12.32PPCh. 12 - Prob. 12.33PPCh. 12 - Prob. 12.34PPCh. 12 - Prob. 12.35PPCh. 12 - Prob. 12.36PPCh. 12 - Prob. 12.37PPCh. 12 - Prob. 12.38PPCh. 12 - Prob. 12.39PPCh. 12 - Prob. 12.40PPCh. 12 - Prob. 12.41PPCh. 12 - Prob. 12.42PPCh. 12 - Prob. 12.43PPCh. 12 - Prob. 12.44PPCh. 12 - Prob. 12.45PPCh. 12 - Prob. 12.46PPCh. 12 - Prob. 12.47PPCh. 12 - Prob. 12.48PPCh. 12 - Prob. 12.49PPCh. 12 - Prob. 12.50PPCh. 12 - Prob. 12.51PPCh. 12 - Arachidic acid is a saturated C20 fatty acid. a....Ch. 12 - Prob. 12.53PPCh. 12 - Prob. 12.54PPCh. 12 - Prob. 12.55PPCh. 12 - Prob. 12.56PPCh. 12 - Prob. 12.57PPCh. 12 - Prob. 12.58PPCh. 12 - Prob. 12.59APCh. 12 - Prob. 12.60APCh. 12 - Prob. 12.61APCh. 12 - Prob. 12.62APCh. 12 - Identify the type of foodcarbohydrate, fat, or...Ch. 12 - Prob. 12.64APCh. 12 - Prob. 12.65APCh. 12 - Prob. 12.66APCh. 12 - Prob. 12.67APCh. 12 - Prob. 12.68APCh. 12 - Prob. 12.69APCh. 12 - Prob. 12.70APCh. 12 - Prob. 12.71APCh. 12 - Prob. 12.72APCh. 12 - Prob. 12.73APCh. 12 - Prob. 12.74APCh. 12 - Prob. 12.75APCh. 12 - Prob. 12.76APCh. 12 - Prob. 12.77APCh. 12 - Prob. 12.78APCh. 12 - Prob. 12.79APCh. 12 - Prob. 12.80APCh. 12 - Prob. 12.81APCh. 12 - Prob. 12.82APCh. 12 - Prob. 12.83APCh. 12 - Prob. 12.84APCh. 12 - Prob. 12.85APCh. 12 - Prob. 12.86APCh. 12 - Prob. 12.87APCh. 12 - Prob. 12.88APCh. 12 - Prob. 12.89CPCh. 12 - Prob. 12.90CPCh. 12 - Laurie acid, a saturated Cl2 fatty acid, is found...Ch. 12 - A person is brought to the emergency room in what...Ch. 12 - Prob. 12.93CPCh. 12 - Prob. 12.94CPCh. 12 - Prob. 1IA.1QCh. 12 - Prob. 1IA.2QCh. 12 - Prob. 1IA.3QCh. 12 - Prob. 1IA.4QCh. 12 - Prob. 1IA.5QCh. 12 - Prob. 1IA.6QCh. 12 - Prob. 1IA.7QCh. 12 - Prob. 1IA.8QCh. 12 - Prob. 2IA.1QCh. 12 - Prob. 2IA.2QCh. 12 - Prob. 2IA.3QCh. 12 - Prob. 2IA.4QCh. 12 - Prob. 3IA.1QCh. 12 - Prob. 3IA.2QCh. 12 - Prob. 3IA.3QCh. 12 - Prob. 3IA.4QCh. 12 - Prob. 3IA.5QCh. 12 - Prob. 1ICCh. 12 - Prob. 2ICCh. 12 - Prob. 3IC
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- (a) Draw the structures of A and B in the following reaction. (i) NaNH2, NH3(1) A + B (ii) H3O+arrow_forwardFor the reaction 2 N2O5(g) → 4 NO2(g) + O2(g), the following mechanism has been proposed: N2O5 →> NO₂+ NO3_(K1) NO2 + NO3 → N2O5 (k-1) NO2 + NO3 → → NO2 + O2 + NO (K2) NO + N2O5- NO2 + NO2 + NO2 (K3) d[N₂O5] __2k‚k₂[N2O5] Indicate whether the following rate expression is acceptable: dt k₁₁+ k₂arrow_forwardConsider the following decomposition reaction of N2O5(g): For the reaction 2 N2O5(g) → 4 NO2(g) + O2(g), the following mechanism has been proposed: N2O5 → NO2 + NO3 (K1) NO2 + NO3 → N2O5 (k-1) NO2 + NO3 → NO2 + O2 + NO (K2) NO + N2O5 → NO2 + NO2 + NO2 (K3) Indicate whether the following rate expression is acceptable: d[N2O5] = -k₁[N₂O₂] + K¸₁[NO₂][NO3] - K¸[NO₂]³ dtarrow_forward
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