
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
Question
Chapter 19, Problem 25P
Interpretation Introduction
Interpretation:
The starting material required to synthesize the given compounds by acylation of enolate is to be provided.
Concept introduction:
The carbon–carbon bond forming reaction, useful for the synthesis of
In carbonyl condensation reaction, the enolate of one carbonyl compound reacts with the carbonyl group of another.
The Claisen condensation between esters containing α-hydrogens, promoted by a base such as sodium ethoxide, affords β-ketoesters.
The intramolecular version is known as Dieckmann Condensation.
Claisen condensation is a reversible reaction.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
MnO2 acts as an oxidant in the chlorine synthesis reaction.
In Potassium mu-dihydroxydicobaltate (III) tetraoxalate K4[Co2(C2O4)4(OH)2], indicate whether the OH ligand type is bidentate.
Imagine an electrochemical cell based on these two half reactions with electrolyte concentrations as given below:
Oxidation: Pb(s) → Pb2+(aq, 0.10 M) + 2 e–
Reduction: MnO4–(aq, 1.50 M) + 4 H+(aq, 2.0 M) + 3 e– → MnO2(s) + 2 H2O(l)
Calculate Ecell (assuming temperature is standard 25 °C).
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
Similar questions
- : ☐ + Draw the Fischer projection of the most common naturally-occurring form of aspartate, with the acid group at the top and the side chain at the bottom. Important: be sure your structure shows the molecule as it would exist at physiological pH. Click and drag to start drawing a structure. ✓arrow_forwardFor a silver-silver chloride electrode, the following potentials are observed: E°cell = 0.222 V and E(saturated KCl) = 0.197 V Use this information to find the [Cl–] (technically it’s the activity of Cl– that’s relevant here, but we’ll just call it “concentration” for simplicity) in saturated KCl.arrow_forwardA concentration cell consists of two Sn/Sn2+ half-cells. The cell has a potential of 0.10 V at 25 °C. What is the ratio of [Sn2+] (i.e., [Sn2+left-half] / [Sn2+right-half])?arrow_forward
- Electrochemical cell potentials can be used to determine equilibrium constants that would be otherwise difficult to determine because concentrations are small. What is Κ for the following balanced reaction if E˚ = +0.0218 V? 3 Zn(s) + 2 Cr3+(aq) → 3 Zn2+(aq) + Cr(s) E˚ = +0.0218 Varrow_forwardConsider the following half-reactions: Hg2+(aq) + 2e– → Hg(l) E°red = +0.854 V Cu2+(aq) + 2e– → Cu(s)E°red = +0.337 V Ni2+(aq) + 2e– → Ni(s) E°red = -0.250 V Fe2+(aq) + 2e– → Fe(s) E°red = -0.440 V Zn2+(aq) + 2e– → Zn(s) E°red = -0.763 V What is the best oxidizing agent shown above (i.e., the substance that is most likely to be reduced)?arrow_forwardCalculate the equilibrium constant, K, for MnO2(s) + 4 H+(aq) + Zn(s) → Mn2+(aq) + 2 H2O(l) + Zn2+(aq)arrow_forward
- In the drawing area below, draw the condensed structures of formic acid and ethyl formate. You can draw the two molecules in any arrangement you like, so long as they don't touch. Click anywhere to draw the first atom of your structure. A C narrow_forwardWrite the complete common (not IUPAC) name of each molecule below. Note: if a molecule is one of a pair of enantiomers, be sure you start its name with D- or L- so we know which enantiomer it is. molecule Ο C=O common name (not the IUPAC name) H ☐ H3N CH₂OH 0- C=O H NH3 CH₂SH H3N ☐ ☐ X Garrow_forward(Part A) Provide structures of the FGI products and missing reagents (dashed box) 1 eq Na* H* H -H B1 B4 R1 H2 (gas) Lindlar's catalyst A1 Br2 MeOH H2 (gas) Lindlar's catalyst MeO. OMe C6H1402 B2 B3 A1 Product carbons' origins Draw a box around product C's that came from A1. Draw a dashed box around product C's that came from B1.arrow_forward
- Classify each of the amino acids below. Note for advanced students: none of these amino acids are found in normal proteins. X CH2 H3N-CH-COOH3N-CH-COO- H3N-CH-COO CH2 CH3-C-CH3 CH2 NH3 N NH (Choose one) ▼ (Choose one) S CH2 OH (Choose one) ▼ + H3N-CH-COO¯ CH2 H3N CH COO H3N-CH-COO CH2 오오 CH CH3 CH2 + O C CH3 O= O_ (Choose one) (Choose one) ▼ (Choose one) Garrow_forwardAnother standard reference electrode is the standard calomel electrode: Hg2Cl2(s) (calomel) + 2e2 Hg() +2 Cl(aq) This electrode is usually constructed with saturated KCI to keep the Cl- concentration constant (similar to what we discussed with the Ag-AgCl electrode). Under these conditions the potential of this half-cell is 0.241 V. A measurement was taken by dipping a Cu wire and a saturated calomel electrode into a CuSO4 solution: saturated calomel electrode potentiometer copper wire CuSO4 a) Write the half reaction for the Cu electrode. b) Write the Nernst equation for the Cu electrode, which will include [Cu2+] c) If the voltage on the potentiometer reads 0.068 V, solve for [Cu²+].arrow_forward2. (Part B). Identify a sequence of FGI that prepares the Synthesis Target 2,4-dimethoxy- pentane. All carbons in the Synthesis Target must start as carbons in either ethyne, propyne or methanol. Hint: use your analysis of Product carbons' origins (Part A) to identify possible structure(s) of a precursor that can be converted to the Synthesis Target using one FGI. All carbons in the Synthesis Target must start as carbons in one of the three compounds below. H = -H H = -Me ethyne propyne Synthesis Target 2,4-dimethoxypentane MeOH methanol OMe OMe MeO. OMe C₂H₁₂O₂ Product carbons' origins Draw a box around product C's that came from A1. Draw a dashed box around product C's that came from B1.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