General, Organic, and Biological Chemistry Seventh Edition
7th Edition
ISBN: 9781305767867
Author: H. Stephan Stoker
Publisher: Cengage Learning
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Chapter 26, Problem 26.95EP
Interpretation Introduction
Interpretation: To arrange bilirubin, urobilin, biliverdin, and bilirubin diglucuronide in the order in which they are encountered during heme catabolism.
Concept introduction: Hemoglobin is a heme protein present in the red blood cells. The protein part is called globin and the non-protein part is heme. Heme is the prosthetic group that contains 4 pyrrole groups bonded together and has an iron atom in the center. The structure of the heme group is:
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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 26 Solutions
General, Organic, and Biological Chemistry Seventh Edition
Ch. 26.1 - Which of the following statements about dietary...Ch. 26.1 - Dietary protein materials as they leave the...Ch. 26.1 - The inactive form of pepsin is converted to its...Ch. 26.1 - Which of the following is not a proteolytic...Ch. 26.2 - The dominant use for the amino acids of the amino...Ch. 26.2 - The most abundant amino acid in the amino acid...Ch. 26.2 - Prob. 3QQCh. 26.3 - Prob. 1QQCh. 26.3 - Prob. 2QQCh. 26.3 - The net effect of transamination is to collect the...
Ch. 26.3 - Prob. 4QQCh. 26.3 - Prob. 5QQCh. 26.3 - Most aminotransferases are specific for the keto...Ch. 26.4 - Which of the following statements concerning the...Ch. 26.4 - Prob. 2QQCh. 26.4 - The two fuels for the urea cycle are a. carbamoyl...Ch. 26.4 - Prob. 4QQCh. 26.4 - Prob. 5QQCh. 26.4 - Prob. 6QQCh. 26.5 - Which of the following statements concerning the...Ch. 26.5 - Prob. 2QQCh. 26.5 - Prob. 3QQCh. 26.5 - Prob. 4QQCh. 26.6 - Prob. 1QQCh. 26.6 - How many of the standard amino acids are...Ch. 26.6 - The simplest pathways for amino acid biosynthesis...Ch. 26.7 - Prob. 1QQCh. 26.7 - Which of the following statements concerning the...Ch. 26.7 - Prob. 3QQCh. 26.7 - In the degradation of heme, the iron atom present...Ch. 26.8 - In degradation of the sulfur-containing amino acid...Ch. 26.8 - Prob. 2QQCh. 26.8 - Prob. 3QQCh. 26.8 - Prob. 4QQCh. 26.9 - Prob. 1QQCh. 26.9 - Prob. 2QQCh. 26.9 - Prob. 3QQCh. 26.10 - Prob. 1QQCh. 26.10 - Prob. 2QQCh. 26.10 - Prob. 3QQCh. 26 - Prob. 26.1EPCh. 26 - Indicate whether each of the following aspects of...Ch. 26 - Indicate whether each of the following pairings of...Ch. 26 - Indicate whether each of the following pairings of...Ch. 26 - Indicate whether each of the following statements...Ch. 26 - Prob. 26.6EPCh. 26 - Prob. 26.7EPCh. 26 - Prob. 26.8EPCh. 26 - Prob. 26.9EPCh. 26 - Prob. 26.10EPCh. 26 - Prob. 26.11EPCh. 26 - Prob. 26.12EPCh. 26 - Prob. 26.13EPCh. 26 - Prob. 26.14EPCh. 26 - Indicate whether each of the following situations...Ch. 26 - Indicate whether each of the following situations...Ch. 26 - Prob. 26.17EPCh. 26 - Prob. 26.18EPCh. 26 - Prob. 26.19EPCh. 26 - Prob. 26.20EPCh. 26 - Prob. 26.21EPCh. 26 - Prob. 26.22EPCh. 26 - Prob. 26.23EPCh. 26 - Prob. 26.24EPCh. 26 - Prob. 26.25EPCh. 26 - Prob. 26.26EPCh. 26 - Prob. 26.27EPCh. 26 - Prob. 26.28EPCh. 26 - Prob. 26.29EPCh. 26 - Prob. 26.30EPCh. 26 - Prob. 26.31EPCh. 26 - Prob. 26.32EPCh. 26 - Prob. 26.33EPCh. 26 - Prob. 26.34EPCh. 26 - Prob. 26.35EPCh. 26 - Prob. 26.36EPCh. 26 - Prob. 26.37EPCh. 26 - Prob. 26.38EPCh. 26 - Prob. 26.39EPCh. 26 - Prob. 26.40EPCh. 26 - Prob. 26.41EPCh. 26 - Prob. 26.42EPCh. 26 - Prob. 26.43EPCh. 26 - Draw the structure of the -keto acid produced from...Ch. 26 - Prob. 26.45EPCh. 26 - Prob. 26.46EPCh. 26 - Prob. 26.47EPCh. 26 - Prob. 26.48EPCh. 26 - Prob. 26.49EPCh. 26 - Prob. 26.50EPCh. 26 - Prob. 26.51EPCh. 26 - Prob. 26.52EPCh. 26 - Prob. 26.53EPCh. 26 - Prob. 26.54EPCh. 26 - Prob. 26.55EPCh. 26 - Prob. 26.56EPCh. 26 - Prob. 26.57EPCh. 26 - Prob. 26.58EPCh. 26 - Prob. 26.59EPCh. 26 - Prob. 26.60EPCh. 26 - Prob. 26.61EPCh. 26 - Prob. 26.62EPCh. 26 - Prob. 26.63EPCh. 26 - Prob. 26.64EPCh. 26 - Prob. 26.65EPCh. 26 - Prob. 26.66EPCh. 26 - Prob. 26.67EPCh. 26 - Prob. 26.68EPCh. 26 - Prob. 26.69EPCh. 26 - Prob. 26.70EPCh. 26 - Prob. 26.71EPCh. 26 - Prob. 26.72EPCh. 26 - Prob. 26.73EPCh. 26 - Prob. 26.74EPCh. 26 - Prob. 26.75EPCh. 26 - Prob. 26.76EPCh. 26 - Prob. 26.77EPCh. 26 - Prob. 26.78EPCh. 26 - Prob. 26.79EPCh. 26 - Prob. 26.80EPCh. 26 - Prob. 26.81EPCh. 26 - Prob. 26.82EPCh. 26 - Prob. 26.83EPCh. 26 - Prob. 26.84EPCh. 26 - Prob. 26.85EPCh. 26 - Prob. 26.86EPCh. 26 - Prob. 26.87EPCh. 26 - Prob. 26.88EPCh. 26 - Prob. 26.89EPCh. 26 - Prob. 26.90EPCh. 26 - Prob. 26.91EPCh. 26 - Prob. 26.92EPCh. 26 - Prob. 26.93EPCh. 26 - Prob. 26.94EPCh. 26 - Prob. 26.95EPCh. 26 - Prob. 26.96EPCh. 26 - Prob. 26.97EPCh. 26 - Which bile pigment is responsible for the...Ch. 26 - Prob. 26.99EPCh. 26 - Prob. 26.100EPCh. 26 - Prob. 26.101EPCh. 26 - Prob. 26.102EPCh. 26 - Prob. 26.103EPCh. 26 - Prob. 26.104EPCh. 26 - Prob. 26.105EPCh. 26 - Prob. 26.106EPCh. 26 - Prob. 26.107EPCh. 26 - Prob. 26.108EPCh. 26 - Prob. 26.109EPCh. 26 - Prob. 26.110EPCh. 26 - Prob. 26.111EPCh. 26 - Prob. 26.112EPCh. 26 - Prob. 26.113EPCh. 26 - Prob. 26.114EPCh. 26 - Prob. 26.115EPCh. 26 - Prob. 26.116EP
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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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