
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
Question
Chapter 19, Problem 51P
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 solution
Students have asked these similar questions
Instructions: Complete the questions in the space provided. Show all your work
1. You are trying to determine the rate law expression for a reaction that you are completing at 25°C. You measure
the initial reaction rate and the starting concentrations of the reactions for 4 trials.
BrO³¯ (aq) + 5Br¯ (aq) + 6H* (aq) → 3Br₂ (l) + 3H2O (l)
Initial rate
Trial
[BrO3]
[H*]
[Br]
(mol/L)
(mol/L) | (mol/L)
(mol/L.s)
1
0.10
0.10
0.10
8.0
2
0.20
0.10
0.10
16
3
0.10
0.20
0.10
16
4
0.10
0.10
0.20
32
a.
Based on the above data what is the rate law expression?
b. Solve for the value of k (make sure to include proper units)
2. The proposed reaction mechanism is as follows:
i.
ii.
BrО¸¯ (aq) + H+ (aq) → HBrO3 (aq)
HBrO³ (aq) + H* (aq) → H₂BrO3* (aq)
iii.
H₂BrO³* (aq) + Br¯ (aq) → Br₂O₂ (aq) + H2O (l)
[Fast]
[Medium]
[Slow]
iv.
Br₂O₂ (aq) + 4H*(aq) + 4Br(aq) → 3Br₂ (l) + H2O (l)
[Fast]
Evaluate the validity of this proposed reaction. Justify your answer.
е.
Д
CH3
D*, D20
C.
NaOMe,
Br
Br
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
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
- Please predict the products for each of the following reactions: 1.03 2. H₂O NaNH, 1. n-BuLi 2. Mel A H₂ 10 9 0 H2SO4, H₂O HgSO4 Pd or Pt (catalyst) B 9 2 n-BuLi ♡ D2 (deuterium) Lindlar's Catalyst 1. NaNH2 2. EtBr Na, ND3 (deuterium) 2. H₂O2, NaOH 1. (Sia)2BH с Darrow_forwardin the scope of ontario SCH4U grade 12 course, please show ALL workarrow_forwardIs the chemical reaction CuCl42-(green) + 4H2O <==> Cu(H2O)42+(blue) + 4Cl- exothermic or endothermic?arrow_forward
- If we react tetraethoxypropane with hydrazine, what is the product obtained (explain its formula). State the reason why the corresponding dialdehyde is not used.arrow_forwarddrawing, no aiarrow_forwardIf CH3COCH2CH(OCH3)2 (4,4-dimethoxy-2-butanone) and hydrazine react, two isomeric products are formed. State their structure and which will be the majority.arrow_forward
- + Reset Provide the correct IUPAC name for the compound shown here. 4-methylhept-2-ene (Z)- (E)- 1-6-5-2-3-4- cyclo iso tert- sec- di tri hept hex oct meth eth pent ane yne ene ylarrow_forward+ Provide the correct IUPAC name for the compound shown here. Reset H3C H H C CH3 CH-CH3 1-3-methylpent ene trans- cis- 5-6-3-1-2-4- tert- tri sec- di cyclo iso but pent hex meth prop eth yl ane ene yne ☑arrow_forwarddrawing, no aiarrow_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
