Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
9th Edition
ISBN: 9781305922198
Author: John E. McMurry
Publisher: CENGAGE L
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Question
Chapter 18.SE, Problem 69GP
Interpretation Introduction
Interpretation:
Given that the enzyme chorismate mutase catalyzes a Claisen rearrangement of chorismate. The structure of prephenate obtained as the product is to be shown.
Concept introduction:
In Claisen rearrangement allyl phenyl ethers undergo rearrangement when heated to 200-250°C to yield an o-allylphenol. It is a case of (3, 3) sigmatrophic rearrangement.
To show:
The structure of prephenate obtained as the product obtained when chorismate undergoes Claisen rearrangement catalyzed by the enzyme chorismate mutase.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Complete the following esterification reactions by drawing the line formulas of the carboxylic acid
and alcohol required to form the ester shown.
catalyst
catalyst
catalyst
apricot fragrance
Show the saponification products of the following ester:
You don't need to draw in the Na+ cation.
catalyst, A
catalyst, A
catalyst, A
What would happen if the carboxylic acid and alcohol groups were on the same molecule? In
essence, the molecule reacts with itself. Draw the structure of the products formed in this manner
using the reactants below. If two functional groups interact with one another on the same molecule,
this is called an “intramolecular" (within one) rather than "intermolecular" (between two or more)
attack.
OH
OH
catalyst
OH
HO
catalyst
catalyst
HO
OH
Chapter 18 Solutions
Student Value Bundle: Organic Chemistry, + OWLv2 with Student Solutions Manual eBook, 4 terms (24 months) Printed Access Card (NEW!!)
Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6PCh. 18.3 - Prob. 7PCh. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...
Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Prob. 16PCh. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Prob. 29MPCh. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 56GPCh. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
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
- Q3: Write in the starting alkyl bromide used to form the following products. Include any reactants, reagents, and solvents over the reaction arrow. If more than one step is required, denote separate steps by using 1), 2), 3), etc. H OH racemic OH OH 5 racemicarrow_forwardDraw the Lewis structure of the SO3-O(CH3)2 complex shown in the bottom right of slide 2in lecture 3-3 (“Me” means a CH3 group) – include all valence electron pairs and formal charges.From this structure, should the complex be a stable molecule? Explain.arrow_forwardPredict all organic product(s), including stereoisomers when applicable.arrow_forward
- What I Have Learned Directions: Given the following reaction and the stress applied in each reaction, answer the question below. A. H2(g) + Cl2(g) 2 HCl(g) Stress applied: Decreasing the pressure 1. What is the Keq expression? 2. What will be the effect in the number of moles of HCl(g)? 3. What will be the Equilibrium Shift or the reaction? B. Fe3O4(s) + 4 H2(g) + heat 53 Fe(s) + 4 H₂O(g) Stress applied: Increasing the temperature 1. What is the Keq expression?. 2. What will be the effect in the volume of water vapor collected? 3. What will be the Equilibrium Shift or the reaction? C. 4 NH3(g) + 5 O2(g) 4 NO(g) + 6 H2O(g) + heat Stress applied: Increasing the volume of the container 1. What is the Keq expression?. 2. What will be the effect in the amount of H₂O? 3. What will be the Equilibrium Shift or the reaction?arrow_forwardConsider the solubility products (Ksp values) for the following compounds:SrSO4 (Ksp = 7.6 x 10−7), BaSO4 (Ksp = 1.5 x 10−9), SrCO3 (Ksp = 7.0 x 10−10), BaCO3 (Ksp = 1.6 x 10−9)Which anion is the harder base, CO32− or SO42−? Justify your answer.arrow_forwardQ1: a) Arrange the compounds in order of decreasing pKa, highest first. ОН ΟΗ ῸΗ дон ОН ОН CI Brarrow_forward
- (4 pts - 2 pts each part) A route that can be taken to prepare a hydrophobic (water-repellent) aerogel is to start with trichloromethylsilane, CH3SiCl3 as the silicon source. a. What is the chemical reaction that this undergoes to form a product with Si-OH groups? Write as complete of a chemical equation as you can. CI CI-SI-CH3 CI b. The formation of a byproduct is what drives this reaction - what is the byproduct (if you didn't already answer it in part (a)) and how/why does it form?arrow_forwardb) Circle the substrate that would not efficiently generate a Grignard reagent upon reaction with Mg in ether. CI Br ד c) Circle the Grignard reagents that contain incompatible functional groups. MgBr HO MgBr MgBr MgBr MgBr HO MgBrarrow_forwardQ2: Predict all organic product(s), including stereoisomers when applicable. PCC OH a) CH2Cl2 Page 2 of 5 Chem 0310 Organic Chemistry 1 HW Problem Sets b) .OH Na2Cr2O7, H+ OH PCC CH2Cl2 c) OHarrow_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
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher: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
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
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
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License