Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 27.SE, Problem 33AP
Assume that acetyl CoA containing a 14C isotopic label in the carboxyl carbon atom is used as starting material and that the mevalonate pathway is followed. Identify the positions in lanosterol where the label would appear.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Describe how the addition of an isoxazolidinone to a substrate directs the stereochemistry of a reaction.
Draw the product when the following compound undergoes ring-closingmetathesis.
D-Gulose exists in aqueous solution as a mixture of a-D-gulopyranose and 6-D-gulopyranose. Choose
Haworth projections for these molecules.
CH2OH
CH2OH
он
Н
он
Н
앤 H
ОН
Н
Он
Он
Н
Он
Н
α-D-Gulopyranose
CH2OH
B-D-Gulopyranose
CH2OH
онт
Н
он
ОН
Ка
Н
Н
Н
Он
Н
Н
ОН
Он
ОН Он
a-D-Gulopyranose
CH2OH
B-D-Gulopyranose
CH2OH
он
Он
онт
H
д Н
Ка
Н
H
Н
Н
ОН
ОН ОН
α-D-Gulopyranose
CH2OH
онт Он
ОН Он
Он Он
B-D-Gulopyranose
CH2OH
онт
Он
배
OH
Н
ОН
Н
H
Н
Н
H
Н
α-D-Gulopyranose
B-D-Gulopyranose
Chapter 27 Solutions
Organic Chemistry
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
Additional Science Textbook Solutions
Find more solutions based on key concepts
45. Calculate the mass of nitrogen dissolved at room temperature in an 80.0-L home aquarium. Assume a total pre...
Chemistry: Structure and Properties
Calculate the lattice energy of CaCl2 using a Born-Haber cycle and data from Appendices F and L and Table 7.5. ...
Chemistry & Chemical Reactivity
The method to determine the volume of a powered solid, liquid and a rock needs to be determined. Concept introd...
Living by Chemistry
Determine the number of protons, neutrons, and electrons in the following atoms: a. a hydrogen atom that has a ...
General, Organic, and Biological Chemistry (3rd Edition)
Real walls are never totally adiabatic. Use your experience to order the following walls in increasing order wi...
Thermodynamics, Statistical Thermodynamics, & Kinetics
Q1. What is the empirical formula of a compound with the molecular formula
Chemistry: A Molecular Approach
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
- Assume that acetyl CoA containing a 14C isotopic label in the carboxyl carbon atom is used as starting material and that the mevalonate pathway is followed. Identify the positions in squalene where the label would appear.arrow_forwardTreatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes configuration but the other does not.arrow_forwardWhich of the following is a hemiacetal? ОН ОН A) H;C-C-OH В) Н,С-С—ОСH Н н ОН нс- OCH3 D) H,C-С—ОСН, С) НС-С—ОН ÓCH3 н A Darrow_forward
- An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers of each other.arrow_forwardCh19-5: Which of the compounds is the intermediate called hemiacetal of the following reaction? 요 HO OH H₂SO (-H₂O) OH HO OH HO HOO O OH OHarrow_forward2305032118517 CHO H-C-OH H-C-OH H₂C₂OH CHO Ho-C-tt A D-aldotetrose yields a mixture of the two compounds shown below when subjected to Kiliani - Fischer Chain extension synthesis. What is the Structure of the aldotetrose? 3 CH₂OH Compound I H-C-OH CHO HO-C-H Ho C-H сно HO-C-H WOO Н-С-он H-C-OH CH ₂ OH Compound II CHO H² C-OH HO-C-H CH₂OH CH ₂ OH CH₂OH CA) (B) (D) (E) Both choices (B) and (C) could be the correct structure of D-erythrose. CHO H₂C-OH HC OH CH ₂ OH ctrl MAND optionarrow_forward
- Describe how mescaline can be synthesized from benzene.arrow_forwardPropose a mechanism for the biosynthesis of limonene from geranyl pyrophosphate.arrow_forwardTreatment of α,β-unsaturated carbonyl compound X with base forms the diastereomer Y. Write a stepwise mechanism for this reaction. Explain why one stereogenic center changes conguration but the other does not.arrow_forward
- Which statement is correct? a. Testosterone and nortestosterone possess a ketone at C-3 conjugated to a single bond at C-4 and a hydroxyl at C-17b. b. Testosterone and nortestosterone possess a ketone at C-4 conjugated to a double bond at C-3 and a hydroxyl at C-17b. c. Testosterone and nortestosterone possess a ketone at C-3 conjugated to a double bond at C-4 and a hydroxyl at C-17b. d. The obviously wrong answer!.arrow_forwardPropose a mechanism for the biosynthesis of a-pinene from farnesyl pyrophosphate.arrow_forwardThe following bicyclic ketone has two a-carbons and three a-hydrogens. When this molecule is treated with D,O in the presence of an acid catalyst, only two of the three a-hydrogens exchange with deuterium. The a-hydrogen at the bridgehead does not exchange. H these two a-hydrogens exchange H. this a-hydrogen does not exchange H How do you account for the fact that two a-hydrogens do exchange but the third does not? You will find it helpful to build models of the enols by which exchange of a-hydrogens occurs.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher: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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Lipids - Fatty Acids, Triglycerides, Phospholipids, Terpenes, Waxes, Eicosanoids; Author: The Organic Chemistry Tutor;https://www.youtube.com/watch?v=7dmoH5dAvpY;License: Standard YouTube License, CC-BY