Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 21, Problem 41P
Interpretation Introduction
Interpretation:
The structure of product formed by the treatment of ethyl acetoacetate with the given reagents is to be drawn.
Concept introduction:
The replacement or substitution of one
In nucleophilic substitution reaction, nucleophile takes the position of leaving group by attacking on the electron deficient carbon atom.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
The following questions concern ethyl (2-oxocyclohexane)carboxylate.(a) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by a Dieckmann cyclization.(b) Write a chemical equation showing how you could prepare ethyl (2-oxocyclohexane)-carboxylate by acylation of a ketone.(c) Write structural formulas for the two most stable enol forms of ethyl (2-oxocyclohexane)carboxylate.(d) Write the three most stable resonance contributors to the most stable enolate derived from ethyl (2-oxocyclohexane)carboxylate.(e) Show how you could use ethyl (2-oxocyclohexane)carboxylate to prepare 2-methylcyclohexanone.(f) Give the structure of the product formed on treatment of ethyl (2-oxocyclohexane)-carboxylate with acrolein (H2C=CHCH=O) in ethanol in the presence of sodium ethoxide
Rank the compounds in each of the following groups in order of their reactivity to electrophilic substitution:
(a) Nitrobenzene, phenol, toluene, benzene
(b) Phenol, benzene, chlorobenzene, benzoic acid
(c) Benzene, bromobenzene, benzaldehyde, aniline
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?
Chapter 21 Solutions
Organic Chemistry - Standalone book
Ch. 21.1 - Prob. 1PCh. 21.1 - Prob. 2PCh. 21.1 - Prob. 3PCh. 21.1 - Prob. 4PCh. 21.1 - Prob. 5PCh. 21.2 - Prob. 6PCh. 21.2 - Prob. 7PCh. 21.2 - Prob. 8PCh. 21.3 - Prob. 9PCh. 21.3 - Prob. 10P
Ch. 21.3 - Prob. 11PCh. 21.4 - Prob. 12PCh. 21.4 - Prob. 13PCh. 21.5 - Prob. 14PCh. 21.5 - Problem 21.15 Write the structure of the Dieckmann...Ch. 21.5 - Prob. 16PCh. 21.5 - Prob. 17PCh. 21.6 - Prob. 18PCh. 21.6 - Prob. 19PCh. 21.6 - Prob. 20PCh. 21.6 - Prob. 21PCh. 21.6 - Prob. 22PCh. 21.7 - Prob. 23PCh. 21.8 - Problem 21.24 Mesityl oxide is an industrial...Ch. 21.8 - Prob. 25PCh. 21.8 - Prob. 26PCh. 21.8 - Prob. 27PCh. 21.8 - Prob. 28PCh. 21 - Prob. 29PCh. 21 - Terreic acid, a naturally occurring antibiotic...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Give the structure of the expected organic product...Ch. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Give the structure of the principal organic...Ch. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - Prob. 45PCh. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - The use of epoxides as alkylating agents for...Ch. 21 - Prob. 49PCh. 21 - Show how you could prepare each of the following...Ch. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - The - methylene ketone sarkomycin has an...Ch. 21 - - Lactone can be prepared in good yield from...Ch. 21 - Prob. 57PCh. 21 - Prob. 58DSPCh. 21 - The Enolate Chemistry of Dianionss The synthetic...Ch. 21 - Prob. 60DSPCh. 21 - Prob. 61DSPCh. 21 - Prob. 62DSPCh. 21 - Prob. 63DSP
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
- Show how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acidarrow_forwardThe compound eutypine is an antibacterial agent isolated from the fungus Eutypa lata. This fungus results in a disease common to vineyards called eutyposis. Give a sequence of reactions that will take the following reactant and give eutypine when the other reactants used in the sequence are acetylene and acetone.arrow_forwardArrange the compounds in order of INCREASING reactivity towards bromination. Toluene, Nitrobenzene, Anisole, Aniline Acetophenone, Bromobenzene, Aniline, Phenol Acetanilide, Benzaldehyde, Toluene, Iodobenzenearrow_forward
- An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.arrow_forwardCompound A undergoes an acid-catalyzed hydrolysis. One of the products (B) that is isolated gives the following 1H NMR spectrum. Identify the compounds A and Carrow_forwardExplain how benzaldehyde and dimedone reacts with each other, and then with the aminotriazole to form compound 1a in the presence of an acid catalyst. Provide a detailed reaction mechanism and explanation.arrow_forward
- The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.arrow_forwardProvide a synthesis for the following transformation. Ethyl acetoacetic ester and any other necessary reagentsarrow_forward
arrow_back_ios
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Macroscale and Microscale Organic ExperimentsChemistryISBN:9781305577190Author:Kenneth L. Williamson, Katherine M. MastersPublisher:Brooks Cole
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Macroscale and Microscale Organic Experiments
Chemistry
ISBN:9781305577190
Author:Kenneth L. Williamson, Katherine M. Masters
Publisher:Brooks Cole