Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 19, Problem 7PP
Practice Problem 19.7
The acid-catalyzed aldol condensation of acetone (just shown) also producs some 2,6-dimethylhepta-2,5-dien-4-one. Give a mechanism that explains the formation of this product.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Give me a clear handwritten answer with explanation
Show how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acid
Kindly answer this question
Chapter 19 Solutions
Organic Chemistry
Ch. 19 - PRACTICE PROBLEM 19.1 (a) Write a mechanism. for...Ch. 19 - Practice Problem 19.2
Since the products obtained...Ch. 19 - Prob. 3PPCh. 19 - PRACTICE PROBLEM 19.4
Write mechanisms that...Ch. 19 - Prob. 5PPCh. 19 - Prob. 6PPCh. 19 - Practice Problem 19.7 The acid-catalyzed aldol...Ch. 19 - Prob. 8PPCh. 19 - Practice Problem 19.9
(a) Provide a mechanism for...Ch. 19 - Prob. 10PP
Ch. 19 - Practice Problem 19.11 Outlined below is a...Ch. 19 - Prob. 12PPCh. 19 - Prob. 13PPCh. 19 - Prob. 14PPCh. 19 - Practice Problem 19.15
Starting with ketones and...Ch. 19 - Practice Problem 19.16 Assuming that dehydration...Ch. 19 - Practice Problem 19.17 What starting compound...Ch. 19 - Practice Problem 19.18
What experimental...Ch. 19 - Prob. 19PPCh. 19 - Practice Problem 19.20
When acrolein (propenal)...Ch. 19 - Prob. 21PPCh. 19 - PRACTICE PROBLEM 19.22
Qutline reasonable...Ch. 19 - Prob. 23PCh. 19 - Show all steps in the following syntheses. You may...Ch. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - 19.28 Show how the diketone at the right could be...Ch. 19 - Prob. 29PCh. 19 - 19.30 Write a detailed mechanism for the following...Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - 19.33 Predict the products from each of the...Ch. 19 - Prob. 34PCh. 19 - Show how each of the following transformations...Ch. 19 - Prob. 36PCh. 19 - What reagents would you use to bring about each...Ch. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - 19.40 When the aldol reaction of acetaldehyde is...Ch. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - 19.43 The following reaction illustrates the...Ch. 19 - What is the structure of the cyclic compound that...Ch. 19 - Prob. 45PCh. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Predict the products from the following reactions....Ch. 19 - Prob. 49PCh. 19 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Allowing acetone to react with 2 molar equivalents...Ch. 19 - (+) Fenchone is a terpenoid that can be isolated...Ch. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - 19.60 Develop a synthesis for the following...Ch. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - Prob. 63PCh. 19 - Prob. 1LGP
Additional Science Textbook Solutions
Find more solutions based on key concepts
Classify each molecule as polar nonpolar. a. CS2 b. SO2 c. CH4 d. CH3CI
Introductory Chemistry (5th Edition) (Standalone Book)
a. Draw the most stable conformation of pentane for rotation about the C-2C-3 bond. b. Draw the least stable co...
Essential Organic Chemistry (3rd Edition)
In qualitative analysis, Ca2+ and Ba2+ are separated from Na+, K+, and Mg2+ by adding aqueous (NH4)2CO3 to a so...
General Chemistry: Atoms First
87. List these substances in order of increasing boiling point:
...
Introductory Chemistry (6th Edition)
The similarity and difference in ionic and covalent bond should be determined. Concept Introduction: The intera...
Living By Chemistry: First Edition Textbook
Use electronegativities to predict the direction of the dipole moments of the following bonds. a. CCl b. CO c. ...
Organic Chemistry (9th 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 intramolecular aldol reaction of 6-oxoheptanal [CH3CO(CH2)4CHO] can yield threecyclic D,E-unsaturated ketones. Give the threeproducts and suggest a mechanism for formingone of the products.arrow_forwardPropose a mechanism for the following reaction, which is a synthesis of PEEK (see Section 26.6a.2).arrow_forward18) Provide a detailed, stepwise mechanism for the acid-catalyzed reaction of 2-butanone with ethylene glycol (HOCH2CH2OH) to produce an acetal.arrow_forward
- 1. Each of the following compounds can be prepared by a mixed aldol condensation reaction. Give the structures of the aldehyde and/or ketone precursors for each aldol product shown. soarrow_forward2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl p-methylcinnamate. Show how this alcohol could be synthesized (a) by an aldol condensation of butanal and (b) by a malonic ester synthesis starting with diethyl malonate.arrow_forward(b) Give both the structures and IUPAC names of the reactants for the compound below formed via a crossed aldol reaction with KOH as promotor. Explain why only one product is formed:arrow_forward
- The following questions pertain to the esters shown and behavior under conditions of the Claisen condensation.(a) Two of these esters are converted to β-keto esters in good yield on treatment with sodium ethoxide and subsequent acidification of the reaction mixture. Which two are these? Write the structure of the Claisen condensation product of each one. (b) One ester is capable of being converted to a β-keto ester on treatment with sodium ethoxide, but the amount of β-keto ester that can be isolated after acidification of the reaction mixture is quite small. Which ester is this? (c) One ester is incapable of reaction under conditions of the Claisen condensation. Which one? Why?arrow_forwardAcid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardThe intramolecular Aldol condensation of 2,6-heptanedione with base may produces two possible B-hydroxyl ketones as shown in the following reaction pathway. CH, (1) OH CH, (A) 3-Methyl-2-cyclohexenone CH, CH, (2) Он CH, 2,6-Heptanedione (B) Methyl(2-methyl-1-cyclobutenyl)ketone (i) Write detailed mechanisms for both the reactions (1) and (2).arrow_forward
- The intramolecular Aldol condensation of 2,6-heptancdione with base may produces two possible Bhydroxyl ketones as shown in the following reaction pathway. CH, (1) OH CH, (A) 3-Methyl-2-cyclohexenone .CH, CH, (2) OH - CH3 2,6-Heptanedione (B) Methyl(2-methyl-1-cyclobutenyl)ketone Write detailed mechanisms for both the reactions (1) and (2).arrow_forwardWrite a detailed mechanism for the following reaction. KCN HCNarrow_forwardI need help determining the starting materials for these three aldol reactions.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 LearningEBK 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
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