Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 25.11, Problem 13P
Interpretation Introduction
Interpretation:
The carbon and hydrogen atoms of
Concept introduction:
The biosynthesis of cholesterol from
In each step, a new intermediate is formed. The formation of protosteryl cation and lanosterol intermediate is an important step in this mechanism.
Deprotonation, migration of hydrogen atoms and methyl groups, takes place in this mechanism.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Does the product have any asymmetric carbon atoms or other stereocenters?
A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Is the product capable of showing optical activity? If it is, explain how.
Given the reaction of the synthesis of ethyl acetate:
CH3COCH3 + Br2 + H3O+ → CH3COCH2Br + HBr + H3O+
Which is the catalyst?
H3O+
CH3COCH3
CH3COCH2Br
Br2
Chapter 25 Solutions
Organic Chemistry - Standalone book
Ch. 25.2 - What fatty acids are produced on hydrolysis of...Ch. 25.3 - Give the structure of the keto acyl-ACP formed...Ch. 25.4 - Prob. 3PCh. 25.4 - Prob. 4PCh. 25.5 - Prob. 5PCh. 25.6 - Write the structural formula and give the IUPAC...Ch. 25.6 - Prob. 7PCh. 25.7 - Locate the isoprene units in each of the...Ch. 25.7 - Prob. 9PCh. 25.9 - Prob. 10P
Ch. 25.9 - Prob. 11PCh. 25.10 - Prob. 12PCh. 25.11 - Prob. 13PCh. 25.11 - Prob. 14PCh. 25.12 - Prob. 15PCh. 25.16 - Prob. 16PCh. 25 - Prob. 17PCh. 25 - Prob. 18PCh. 25 - Prob. 19PCh. 25 - Pyrethrins are a group of naturally occurring...Ch. 25 - Prob. 21PCh. 25 - Prob. 22PCh. 25 - Prob. 23PCh. 25 - Prob. 24PCh. 25 - Prob. 25PCh. 25 - Prob. 26PCh. 25 - Prob. 27PCh. 25 - Prob. 28PCh. 25 - A synthesis of triacylglycerols has been described...Ch. 25 - Prob. 30PCh. 25 - Prob. 31PCh. 25 - Prob. 32PCh. 25 - Prob. 33DSPCh. 25 - Prob. 34DSPCh. 25 - Prob. 35DSPCh. 25 - Prob. 36DSPCh. 25 - Prob. 37DSPCh. 25 - Prob. 38DSP
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
- It is well reported that the antiallergic activity of Claritin (loratadine) is not only the result of the drug's action but it is also because of the action of two active metabolites. Draw the chemical structures of the corresponding metabolites and describe the type of the biochemical transformations involved. 1. CH3 ci Loratadine (Claritin)arrow_forwardExplain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardExplain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position. Write the role of Corticosteroids in Pharmaceutical field. Write the rich source of Vitamin D. Write the metabolic pathway of Vitamin D to its most active form and which are the organ involved.arrow_forward
- Prostaglandins are a class of eicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax Km = mM/min mMarrow_forwardProstaglandins 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?…arrow_forwardWhich one of the following statements about arene oxides is FALSE? O The NIH shift is what makes arene oxides carcinogenic. O Ring opening of an arene oxide can afford an addition product and/or a rearranged product. O Large polycyclic aromatic hydrocarbons such as benzo[a]pyrene are especially susceptible to arene oxide formation. The NIH shift mechanism was discovered at the National Institutes of Health. O Cytochrome P450 is the powerful biological oxidant that epoxides an arene to give an arene oxide.arrow_forward
- What is the product of the starting material D-glyceraldehyde which will (1) produce aldaric acid upon reacting with HNO3 + H2O, NaOCH2, NH2OH, and (CH3CO)2O + NaOCOCH3 (2) produce tartaric acid upon reacting with HNO3 + H2O, NaOCH3, NH2OH, and (CH3CO)2O + NaOCOCH3arrow_forwardTreatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forwarda-phellandrene and ß-phellandrene are two isomeric diene-containing terpene compounds isolated from eucalyptus plants that are used in fragrances due to their minty and citrusy odors. Use these two compounds to answer the following two questions: a. The addition of 1 equivalent of bromine at room temperature to the phellandrenes will give three possible di-brominated products. Select either a- or ß-phellandrene for this question and draw it in the left box - you can answer this question with either isomer. Draw all three products in the colored boxes depicted - you do not need to depict newly formed stereocenters or show mechanisms. OR a-phellandrene B-phellandrene product 1 select either a- or B-phellandrene product 2 Br₂ room temperature 3 possible products (see below) product 3arrow_forward
- a. (S)-Penicillamine, an amino acid that does not occur in proteins, is used as a copper chelating agent to treat Wilson's disease, an inherited defect in copper metabolism. (R)-Penicillamine is toxic, sometimes causing blindness. Draw the structures of (R)- and (S)- penicillamine. b. What disulfide is formed from oxidation of (S)-penicillamine?arrow_forwardProstaglandins are a class of cicosanoids, fatty acid derivatives with a variety of extremely potent actions on vertebrate tissues. They are responsible for producing fever and inflammation and its associated pain. Prostaglandins are derived from the 20- carbon fatty acid arachidonic acid in a reaction catalyzed by the enzyme prostaglandin endoperoxide synthase. This enzyme, a cyclooxygenase, uses oxygen to convert arachidonic acid to PGG2, the immediate precursor of many different prostaglandins. Rate of formation of PGG2 with 10 mg/ml ibuprofen (mM/min) Arachidonic acid (mM) Rate of formation of PGG2 (mM/min) 0.190 12.3 0.228 13.9 0.342 17.5 0.570 1.33 22.2 28.8 7.71 8.88 11.9 16.3 24.0 The kinetic data given in the table are for the reaction catalyzed by a mutant of prostaglandin endoperoxide synthase. Focusing here on the first two columns, determine the Vmax and Km of the enzyme. Vmax = Km mM/min mMarrow_forwardDraw the structure of the organic product formed when the following compounds undergo the three-step reaction sequence indicated. Highlight, by using the "graded select" tool and clicking on, the carbon atoms in the product that come from the diethyl malonate. 1. NaOC2H5, C2H5OH 2. NaOH, H2O Br 3. Нзо", heatarrow_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
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole