Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 25.18, Problem 37P
Draw the individual 1,2-hydride and 1,2-methyl shifts responsible for conversion of the protosterol cation to lanosterol. How many hydride shifts are involved? How many methyl shifts?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Show the effect of conjugation on the carbonyl absorption in an IR spectrum ?
Provide the correct product for the following series of transformation. Hint: The product has a H NMR spectrum with only 2 resonances with relative H integrations of 3:1.
1. Br2
2. 3 eq. NaNH2, NH3
3. CH3I
?
Br.
Br
H3C
CH3
A)
CH3
C)
CH3
B)
D)
=CH3
A
B
D
Draw the kinetic and thermodynamic enolates formed when 3-methylbutan-2-one (methyl isopropyl ketone) is treated
with base. Include charges. Draw the oxyanion species; do not draw carbanion resonance forms.
Draw the kinetic enolate.
Draw the thermodynamic enolate.
Select
Draw
Rings
More
Erase
Select
Draw
Rings
More
Erase
H
H
Q
of
Chapter 25 Solutions
Organic Chemistry
Ch. 25.6 - Prob. 2PCh. 25.6 - Prob. 3PCh. 25.6 - Why does the OH group add to the -carbon rather...Ch. 25.6 - Prob. 5PCh. 25.6 - How many molecules of NADH are formed from the...Ch. 25.7 - Prob. 7PCh. 25.7 - Prob. 8PCh. 25.7 - The oxidation of glyceraldehyde-3-phosphate to...Ch. 25.7 - Prob. 10PCh. 25.8 - Prob. 11P
Ch. 25.8 - Prob. 12PCh. 25.8 - Prob. 13PCh. 25.8 - Propose a mechanism for the reduction of...Ch. 25.9 - Prob. 15PCh. 25.9 - Prob. 16PCh. 25.10 - Acid-catalyzed dehydration reactions are normally...Ch. 25.10 - Prob. 18PCh. 25.10 - Prob. 19PCh. 25.10 - Acid-catalyzed dehydration reactions are normally...Ch. 25.10 - Prob. 21PCh. 25.10 - Prob. 22PCh. 25.11 - Prob. 23PCh. 25.12 - a. What is the name of the enzyme that converts...Ch. 25.15 - Prob. 25PCh. 25.16 - Prob. 26PCh. 25.16 - Prob. 27PCh. 25.17 - Propose mechanisms for the Claisen condensation...Ch. 25.17 - Prob. 29PCh. 25.17 - Propose a mechanism for the conversion of...Ch. 25.17 - Propose a mechanism for the biosynthesis of...Ch. 25.17 - Propose a mechanism for the conversion of the E...Ch. 25.17 - The fluoro-substitued geranyl pyrophosphate shown...Ch. 25.17 - Prob. 35PCh. 25.18 - Draw the individual 1,2-hydride and 1,2-methyl...Ch. 25 - Prob. 38PCh. 25 - Prob. 39PCh. 25 - Prob. 40PCh. 25 - Prob. 41PCh. 25 - Prob. 42PCh. 25 - Prob. 43PCh. 25 - Prob. 44PCh. 25 - Prob. 45PCh. 25 - Prob. 46PCh. 25 - Prob. 47PCh. 25 - Prob. 48PCh. 25 - Prob. 49PCh. 25 - Prob. 50PCh. 25 - Prob. 51PCh. 25 - Prob. 52PCh. 25 - Prob. 53PCh. 25 - Prob. 54PCh. 25 - Prob. 55PCh. 25 - Prob. 56PCh. 25 - Prob. 57PCh. 25 - Prob. 58PCh. 25 - Prob. 59PCh. 25 - Prob. 60PCh. 25 - Prob. 61PCh. 25 - Prob. 62PCh. 25 - UDP-galactose-4-epimerase converts UDP-galactose...Ch. 25 - A student is trying to determine the mechanism for...Ch. 25 - What would be the results of the experiment in...Ch. 25 - Prob. 66PCh. 25 - Propose a mechanism for the biosynthesis of...Ch. 25 - Eudesmol is a sesquiterpene found in eucalyptus....
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
- Identify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forwardDraw the three intermediates, including resonance structures, for the attack of nitronium ion on pyridine. Which position(s) is favored? Why?arrow_forwardIdentify products A and B from the given 1H NMR data. a.Treatment of CH2=CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A? b.Treatment of acetone [(CH3)2C=O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?arrow_forward
- In the given reactions both E1 products went through carbocation rearrangements before elimination occurred. Does the mechanism in each reaction involve a hydride shift or a methyl shift? O Hold and drag to reorder 1. = Hydride shift 2. = Methyl shift = Hydride shift = Methyl shift Br CH,CH,OH 1) heat CH,CH,OH heat Br 2)arrow_forwardSearch a reaction scheme for each reaction and draw the step-by-step mechanism using curved arrows for the following reactions. Explain how the IR spectrum (IR peaks of the functional groups) of the product would differ from that of the reactant in each reaction. Oxidation of alcohol using Bleach Epoxidation of alkenes using MCPBA Williamson Ether synthesis Grignard reactionarrow_forwardDraw the two possible intermediates for the attack of the nitronium ion on naphthalene including the important resonance structures. Which position is favored? Why?arrow_forward
- In addition to α cleavage, some aldehydes and ketones undergo the McLafferty rearrangement. In the McLafferty rearrangement, a hydrogen on a carbon three atoms from the C=O is transferred to the carbonyl oxygen and a carbon–carbon bond is broken. This process forms an alkene and the radical cation derived from an enol, which appears as a fragment in the mass spectrum.a.Draw the products formed from the McLafferty rearrangement of 1phenylpentan-1-one, and identify the fragment that results in the given mass spectrum.arrow_forwardSearch a reaction scheme for each reaction and draw the step-by-step mechanism using curved arrows for the following reactions. Explain how the IR spectrum (IR peaks of the functional groups) of the product would differ from that of the reactant in each reaction Grignard reaction Reduction of aldehydes or ketones Acetal or Ketal formation Wittig reactionarrow_forwardDraw a mechanism of a reversible reaction of acetophenone and strong acid (H-A) to form a protonated acetophenone and a weak base. Draw all the electron pairs of the molecules and the arrows. Predict 1H NMR spectra of acetophenone and the protonated acetophenone.arrow_forward
- 6. Which of the following is a major product of the reaction sequence shown in the box? H2NNH2 КОН of H3CO ROH, Heat AICI3 A) H3CO H3CO D) H3CO H2NHN 1H NMR of the major product: Expansion aromatic region: 9H, singlet 2H,doublet 2H, doublet CH 3H, singlet 2H, singlet PPMarrow_forwardExplain why 92% of 2,4-pentanedione exists as the enol tautomer in hexane but only 15% of this compound exists as the enol tautomer in water. The enol tautomer can form hydrogen bonds both with hexane and water, but the keto tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the keto tautomer can form a hydrogen bond with water, which stabilizes it. The keto tautomer can form hydrogen bonds both with hexane and water, but the enol tautomer can form hydrogen bonds with water only. Neither the keto nor the enol tautomer can form hydrogen bonds with hexane, but the enol tautomer can form an intramolecular hydrogen bond, which stabilizes it.arrow_forwardDraw Intermediate CH3OH₂+ protonation H H3C -0 H Q CH3OH deprotonation loss of H₂O elimination H3C :0 ÖH -CH3 Draw Intermediate CH3OH deprotonatio Please select a drawing or reagarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY