Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 19, Problem 52P
Interpretation Introduction
Interpretation:
The base-catalyzed condensation reaction taking place between a malonic ester and 4-methyl-3-penten-2-one, leading to the formation of Dimedone, is to be shown.
Concept introduction:
When a compound containing an active methylene group is treated with a base, the proton is abstracted by the base and a carbon center nucleophile is generated. In the α,β-unsaturated carbonyl system, the β-position is electron deficient due to the conjugation of the carbon–carbon double bonds. The nucleophile attacks at the center and an aldol type condensation enables the ring closure.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
how to synthesize 2-phenylclohexanone from cyclohexanone?
Show how to synthesize 3-nitro-4-propoxybenzoic acid from phenol, C6H5OH and any reagents that you need.
2-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.
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 - 19.50 (+)-Fenchone is a terpenoid that can be...Ch. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - Prob. 54PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Prob. 57PCh. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - 19.60 Write the structures of the three products...Ch. 19 - Prob. 1LGPCh. 19 - Which hydrogen atoms in the following ester are...Ch. 19 - Prob. 2QCh. 19 - 19.3 What starting materials could be used in a...Ch. 19 - Supply the missing reagents, intermediates, and...Ch. 19 - Prob. 5QCh. 19 - Prob. 6QCh. 19 - Prob. 7QCh. 19 - Prob. 8Q
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
- Ethylene oxide is the starting material for the synthesis of 1,4-dioxane. Propose a mechanism for each step in this synthesis.arrow_forwardPropose a synthesis of the anti-inflammatory drug Fenclorac from phenylcyclohexane.arrow_forwardProvide the structure of the two organic product(s) which results when 2-bromo-2-methylbutane is treated with sodium ethoxide.arrow_forward
- Show how the benzyl methyl ether can be synthesized from benzene:arrow_forwardShow how you would synthesize octan-2-one from each compound. You may use any necessary reagents heptanoic acidarrow_forwardSynthesize the following compound from cyclohexanone and any other organic and inorganic reagents you need.arrow_forward
- Show how to synthesize 5-nonanone from 1-bromobutane as the only organic starting material.arrow_forwardH₂C CH3 Show how the compound can be synthesized from benzene and alkyl chlorides.arrow_forward2-Phenylindole is prepared from the reaction of acetophenone and phenylhydrazine, a method known as the Fischer indole synthesis. Propose a mechanism for this reaction. (Hint: the reactive intermediate is the enamine tautomer of the phenylhydrazone.)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 Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning