As presented in the chapter, the Sonogashira coupling reaction is commonly used tocreate diaryl alkynyl structures. However, it can also be used to create divinyl alkynylstructures. The following sequence of reactions creates such a product. Write possiblereactants that would be placed in the boxes in the sequence.Si (Me)3SiMe3OSiMegOSiMegPd(OAc), Cul, Et NHS-

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Answered: As presented in the chapter, the…

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

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.69P

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It is typically very difficult to do a substitution reaction on an aromatic ring when the leaving group is flanked by two other bulky substituents. Moreover, in Section 22.3, we found that nucleophilic aromatic substitution requires strongly electron-withdrawing groups on the benzene ring. However, Pd-catalyzed coupling allows entry into such products. As examples, write the products of the following reactions and state which coupling reaction is being utilized.
The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. It is proposed that NaOH first converts the a-haloketone to the substituted cyclopropanone shown in brackets and then to the sodium salt of cyclopentanecarboxylic acid. (a) Propose a mechanism for base-promoted conversion of 2-chlorocyclohexanone to the proposed intermediate. (b) Propose a mechanism for base-promoted conversion of the proposed intermediate to sodium cyclopentanecarboxylate.
Draw the organic product expected from the reaction. Include all hydrogen atoms. Note that K2Cr2O7K2Cr2O7 is present in excess. CH3CH2CH2OH+K2Cr2O7(aq) −→−−−H2SO4
The reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin production. Write down the reaction mechanisms of these reactions and explain why.
Based on the following seven-step synthetic scheme, answer the questions below. Indicate, in the schematic, the reagents you would use in each are available in the following inventory reagents from an FDA lab. NaCl, CH3OH, terbutanol, K, Na, K2SO4, THF, TsCl, NaOCH3, B2H6, H2O, H3PO4 85%, H2O2, H2O nanopura, PCC, K2Cr2O7, H2SO4, Mg, CH3Br, Cl2, NaOH, HBr 5%, HBr conc., fenolftaleína, dextrina, NaF, KMnO4, HCl 1%, CaCO3, C2H2, C6H6, H2, Pt, CCl4
The reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin. Write down the reaction mechanisms of these reactions and explain why.
The nitro groups on the benzene ring in the reactant serve two purposes.One is to let you know what atoms in the reactant correspond to what atomsin the product. But what role do the nitro groups play electronically – whywould the reaction be much slower if these nitro groups weren’t attached tothose benzene carbons? Draw any relevant structures to support youranswer.
Q9:- Outline a possible laboratory, synthesis of each of the following compounds from benzene and/or toluene, using any needed aliphatic and inorganic reagents, (a) m-bromophenol (b) 5-bromo-2-methylphenol Q10:- Explain how Esters are more reactive than amides in nucleophilic acyl substitution reactions.
(b) The activating and deactivating groups could affect the position(s) of the next incoming group(s) to the benzene ring. Based on the structure below, analyze and explain the group(s) on the benzene ring is activating or deactivating group. Then, identify the product(s) formed from the following reactions. NH, CC, CH;CH,COCI AICI, (i) NH, HNO, H,SO, (ii) H Br AICI, (iii) Page 3 of 4
The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.
Using the Grignard reaction, NBS, NaCN and any other reagents, synthesize Phenylacetone from Toluene, You can use any other reagents necessary. List all the reagents and conditions needed in each step to account for the formation of the product(s).
Nomenclature: provide the systematic names or structure of each of the following compounds. Include E/Z/R/S where relevant.

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