EP ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582453
Author: Brown
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 19, Problem 19.70P
In Problem 7.28, we saw this two-step sequence in Johnson’s synthesis of the steroid hormone progesterone. Propose a structural formula for the intermediate formed in Step 3 and a mechanism for its conversion in Step 4 to progesterone.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
the organic compound 2-heptanone, belonging to the ketone family, is responsible for the strong penetrating odor in Roquefort cheeses. Starting from acetylene as the starting reagent, propose a synthesis line with the reaction mechanisms involved for the synthetic obtaining of 2-heptanone and use it as a food additive in analogous cheeses.
Prostaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in
prostaglandin synthesis involves the conversion of the 20-carbon fatty acid arachidonic acid to PGG2 by the enzyme prostaglandin endoperoxide synthase, or cyclooxy:
Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically.
Arachidonic acid
20₂
0.5
1.0
1.5
2.5
3.5
cyclooxrygenase
PGG₂
JOH
محمد
The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48
[arachidonic acid] (uM)
(1) v(uM/min) (2) v(uM/min)
23.5
32.2
36.9
41.8
44.0
16.67
25.25
30.49
37.04
38.91
Ibuprofen
A. Plot the data in standard Michaelis-Menten form as well as in double-reciprocal form.
B. Determine Vmax and Km for the enzyme.
C. Based on this limited data set, what type of inhibition does ibuprofen likely exhibit?…
Acetylenic fatty acids are found in many tropical plants. Compound H, C18H2502, is one such compound; it absorbs 5 equivalents of H2 when treated
with H2 over a Pd/C catalyst. Ozonolysis of compound H produces the following products:
pentanal (CH3(CH2)3CHO)
2-охоасetic acid (HOOCCHO)
oxalic acid (HooccOOH)
nonanedioic acid (HOOC(CH2)7COOH)
Draw the structure of compound H.
• You do not have to consider stereochemistry.
• You do not have to explicitly draw H atoms.
..
Chapter 19 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 19.2 - Prob. 19.1PCh. 19.2 - Prob. 19.2PCh. 19.2 - Prob. 19.3PCh. 19.3 - Prob. 19.4PCh. 19.3 - Prob. 19.5PCh. 19.3 - Prob. 19.6PCh. 19.5 - Prob. 19.7PCh. 19.5 - Prob. 19.8PCh. 19.5 - Prob. 19.9PCh. 19.6 - Prob. 19.10P
Ch. 19.6 - Prob. 19.11PCh. 19.7 - Prob. 19.12PCh. 19.8 - Prob. 19.13PCh. 19.8 - Prob. 19.14PCh. 19.8 - Prob. 19.15PCh. 19.8 - Prob. 19.16PCh. 19.9 - Prob. 19.17PCh. 19.9 - Prob. AQCh. 19.9 - Prob. BQCh. 19.9 - Prob. CQCh. 19.9 - Prob. DQCh. 19.9 - Prob. EQCh. 19.9 - Prob. FQCh. 19.9 - Prob. GQCh. 19.9 - Intermediate G in Synthesis III is produced as a...Ch. 19.9 - Prob. IQCh. 19.9 - Prob. JQCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Cyclohexene can be converted to...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Draw structural formulas for the -ketoesters...Ch. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Propose a synthesis for each ketone, using as one...Ch. 19 - Prob. 19.35PCh. 19 - Claisen condensation between diethyl phthalate and...Ch. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Enamines normally react with methyl iodide to give...Ch. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Show experimental conditions by which to carry out...Ch. 19 - Prob. 19.55PCh. 19 - The compound 3,5,5-trimethyl-2-cyclohexenone can...Ch. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - The widely used anticoagulant warfarin (see...Ch. 19 - Following is a retrosynthetic analysis for an...Ch. 19 - Following are the steps in one of the several...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - In Problem 7.28, we saw this two-step sequence in...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - The following molecule undergoes an intramolecular...
Additional Science Textbook Solutions
Find more solutions based on key concepts
The active ingredient in Tylenol and a host of other over-the-counter pain relievers is acetaminophen (C8H9NO2)...
Chemistry: Atoms First
Q1. What is the empirical formula of a compound with the molecular formula
Chemistry: A Molecular Approach (4th Edition)
For Practice 1.1
Is each change physical or chemical? Which kind of property (chemical or physical) is demonst...
Principles of Chemistry: A Molecular Approach (3rd Edition)
4. 38 Strontium has four naturally occurring isotopes, with mass numbers 84, 86, 87, arid 88.
a. Write the atom...
Basic Chemistry (5th Edition)
Practice Problem 1.22 Which of the following alkenes can exist as cis-trans isomers? Write their structures. Bu...
Organic Chemistry
Describe the orbitals used in bonding and the bond angles in the following compounds: a. CH3O b. CO2 c. H2CO d....
Organic Chemistry (8th Edition)
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.arrow_forwardTerpin, prepared commercially by the acid-catalyzed hydration of limonene, is used medicinally as an expectorant for coughs. (a) Propose a structural formula for terpin and a mechanism for its formation. (b) How many cis, trans isomers are possible for the structural formula you propose?arrow_forwardClaisen condensation between diethyl phthalate and ethyl acetate followed by saponification, acidification, and decarboxylation forms a diketone, C9H6O2. Propose structural formulas for compounds A and B and the diketone.arrow_forward
- Complete the statements by providing the reagents necessary to complete each step of the synthesis. Ketone reacted with CO₂H and then yielded a derivative, which was treated with 1) (i) C6H5MgBr (ii) H3O+ 2) (i) DIBAL-H (ii). H3O+ 3) Sia2BH,H202, NaOH 4) CH2N2 (diazamethane) CO₂C2H5 5) PCC (an oxidant) 6) H2SO4, H2O, heat 7) HgSO4/ H2SO4 8) C₂H5OH, H3O*, heat TABLE OF REAGENTS to form an unsaturated carboxylic acid, treatment with to yield unsaturated aldehyde as the final product. CHO MacBook Air 9) C6H5 CH2 P(C6H5)3; NaOH 10) PCC (an oxidant) 11) NaCN, H₂SO4 12) PhCH2CHO, H3O*arrow_forwardIsoerythrogenic acid, C18H26O2, is an acetylic fatty acid that turns a vivid blue on exposure to UV light. On Catalytic hydrogenation over a palladium catalyst, five molar equivalents of hydrogen are absorbed, and stearic acid, CH3(CH2)16CO2H, is produced. Ozonolysis of isoerythrogenic acid yields the following products: formaldehyde, CH2O, malonic acid, HO2CCH2CO2H, adipic acid, HO2C(CH2)4CO2H, and the aldehyde carboxylic acid, OHC(CH2)6CO2H. Provide a structure for isoerythrogenic acid.arrow_forwardPropose a reagent or reagents for Steps 2–7 and 9.arrow_forward
- Using your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH OH Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: 1 (a) (CH3)3 CO K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 (c) ethylene oxide Br (e) m-chloroperoxybenzoic acid OH (mCPBA) (f) pyridinium chlorochromate (PCC) || Ⓡ (g) H₂SO4 (anhydrous) (h) NaOH (i) PBr3 (j) Na, NH3 (1) (k) NBS, heat (N-bromosuccinimide) Previous Nextarrow_forward(c) The structures of lycopene, beta-carotene and retinol are shown below. Lycopene Beta-carotene H3C CH; CH3 CH3 OH Retinol (vitamin A) CH3 Using appropriate reaction mechanisms: (i) Show how lycopene is converted into beta-carotene. (ii) Briefly explain how retinol is formed from beta-carotene.arrow_forwardDraw the structural formula for the major product of the following reactions.arrow_forward
- Grignard reagent is a versatile tool in synthetic organic chemistry. Using bromocyclopentane as a starting material, show how a Grignard reagent, X, is synthesized. Reaction of X with water produces compound Y while treatment in carbon dioxide followed by hydrolysis forms compound Z. 3-methyl-2butanone reacts with X and hydrolyses to yield compound AA. Draw the structural formulae of compounds Y, Z and AA and write the chemical equations respectively.arrow_forwardUsing your reaction roadmap as a guide, show how to convert 1-butanol and ethanol into racemic 2-ethoxy-1-butanol. You must use 1-butanol and ethanol as the source of all carbon atoms in the ether product. (1) (2) (3) OH (4) 2-ethoxy-1-butanol (racemic) OH Suggest reagents and experimental conditions for each step in this synthesis. From the choices provided, suggest appropriate reagents for each step. More than one reagent may be necessary. Use the minimum number of steps possible. Enter your answer as a letter, or a series of letters, in the order necessary to bring about the steps shown. Reagents: OH (c) ethylene oxide (a) (CH3)3CO¯K+, THF (d) H₂SO4, H₂O (b) OsO4, H₂O2 Br OH + (9) H₂ SO4 (anhydrous) Na, NH3 (1) (k) NBS, heat (e) m-chloroperoxybenzoic acid (mCPBA) (f) pyridinium chlorochromate) PBr3 (PCC) (h) NaOH (N-bromosuccinimide) Previous Nextarrow_forwardThe tosylate of a primary alcohol normally undergoes an SN2 reaction with hydroxide ion to give a primary alcohol. Reaction of this tosylate, however, gives a compound of molecular formula C7H12O. Propose a structural formula for this compound and a mechanism for its formation.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
IR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=_TmevMf-Zgs;License: Standard YouTube License, CC-BY