Perhydroazulene derivatives have shown usefulness in electronic display applications. (Beilstein J. Org. Chem. 2012, 8, 403-410) In a study to find an efficient route for the synthesis of the perhydroazulene skeleton, compound 1 was heated in an aqueous basic solution. (J. Org. Chem. 1983, 48, 5285-5288) The resulting intramolecular aldol condensation gave compound 2, a perhydroazulene derivative with the molecular formula C₁0H₁4O. Propose a structure for 2. Base C10H140 Compound 2

Perhydroazulene derivatives have shown usefulness in electronic display applications. (Beilstein J. Org. Chem. 2012, 8, 403-410) In a study to find an efficient route for the synthesis of the perhydroazulene skeleton, compound 1 was heated in an aqueous basic solution. (J. Org. Chem. 1983, 48, 5285-5288) The resulting intramolecular aldol condensation gave compound 2, a perhydroazulene derivative with the molecular formula C₁0H₁4O. Propose a structure for 2. Base C10H140 Compound 2

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter17: Carboxylic Acids

Section: Chapter Questions

Problem 17.53P

See similar textbooks

Similar questions

We have seen that the alpha carbon atom of an enamine can function as a nucleophile in a Michael reaction, and in fact, enamines can function as nucleophiles in a wide variety of reactions. For example, an enamine will undergo alkylation when treated with an alkyl halide. Draw the structure of intermediate A and the alkylation product B in the following reaction scheme (J. Am. Chem. Soc. 1954, 76, 2029-2030): TSOH -H₂O NH A 1) CHgI 2) H₂O+ B + NH Modify the given copy of the starting material to draw compound A. If needed, use the single bond tool to interconvert between double and single bonds. Edit Drawing
The Arndt-Eistert synthesis involves a rearrangement (known as a Wolff Rearrangement) with concomitant evolution of nitrogen gas. This reaction has been modified by Georg (J. Am. Chem. Soc. 2010, 132, 15512) to result in a "vinylogous" Wolff Rearrangement (not covered in class). Propose a mechanism for Georg's variation shown below (hint: there's a ketene intermediate). Bn. N O OEt №₂ Bn CO₂Et
Provide a retrosynthetic pathway from the following compound. Indicate reagents needed for each transformation...
Carbodiimides are excellent coupling agents to use to allow an amide or ester coupling to occur under milder conditions. DCC (dicyclohexylcarbodiimide) is extremely common, but the byproduct is insoluble and can contaminate products, whereas other coupling agents have different byproducts with different products. DIC (diisopropylcarbodiimide) and its byproduct are soluble and are easily removed from a solid-phase synthesis. Draw a full mechanism for the amide coupling shown below using DIC as a coupling agent. OH CH3NH₂ -N=C=N- base HINT: The first step of the mechanism uses the organic base to deprotonate something... lohexane as When doing solid-phase peptide synthesis, it is vitally important to get the amino acids in the correct order. However, all amino acids have an amine handle and a carboxylic acid handle, so it's easy to couple an amino acid with itself or in the wrong sequence. How can a chemist ensure that they make only the sequence Gly-Ala-Arg, without ending up with the…
The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q. Propose a mechanism for the conversion of (D) to phensuximide.
When there is Treatment of Compound E with sodium amide and then methyl iodide it does not produce the desired product F. It instead forms Compound G. Why does this happen?.
The following three derivatives of succinimide are anticonvulsants that have found use in the treatment of epilepsy, particularly petit mal seizures. Q.Propose a mechanism for the formation of (A).
Q.2). How will you compare briefly the reactivity of Pyridine and 2-methoxy Pyridine with Furan also explain which one is more reactive toward electrophilic and nucleophilic substitution rxns? Q3). Outline a possible synthetic route for the preparation of a sulfa drug (sulfa pyridine) from benzene.
The widely used anticoagulant warfarin (see Chemical Connections: From Moldy Clover to a Blood Thinner in Chapter 18) is synthesized from 4-hydroxycoumarin, benzaldehyde, and acetone as shown in this retrosynthesis. Show how warfarin is synthesized from these reagents.
) Cinnamaldehyde is used in artificial cinnamon flavoring. Show how cinnamaldehydeis synthesized by a crossed aldol condensation followed by dehydration.H CHcinnamaldehyde C COH(b) Adding acetophenone slowly to a cold solution of LDA produces the enolate of acetophenone; but adding LDA slowly to a cold solution of acetophenone produces acondensation product. Show the reactions happening in each case, and explain why weobserve such different results
Synthesize Chloramphenicol from Toluene or Benzaldehyde. Draw and explain step by step please.(p.s: if you can, can you write what the reagents does?) (Drug Chemistry)
20.5 Provide reasonable mechanisms for the following transformations. a. b. NH₂ BrMg MgBr HS -NH H, quench e НО OH