ot Treatment of a carboxylic acid with trifluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with alcohol to give an ester. (CF3CO)20 R OH R'OH + CF3CO₂H CF3 R OR' Using the reaction of acetic acid as an example, propose a structure for the first intermediate in the reaction to form the unsymmetrical anhydride. • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na+, I, in your answer. In cases where there is more than one answer, just give one. 90-87 Θ / Sn t ? ChemDoodle Cengage Learning Cengage Technical Support Previous Next> Email Instructor Save and

ot Treatment of a carboxylic acid with trifluoroacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with alcohol to give an ester. (CF3CO)20 R OH R'OH + CF3CO₂H CF3 R OR' Using the reaction of acetic acid as an example, propose a structure for the first intermediate in the reaction to form the unsymmetrical anhydride. • You do not have to consider stereochemistry. • Do not include counter-ions, e.g., Na+, I, in your answer. In cases where there is more than one answer, just give one. 90-87 Θ / Sn t ? ChemDoodle Cengage Learning Cengage Technical Support Previous Next> Email Instructor Save and

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

Chapter7: Alkynes

Section: Chapter Questions

Problem 7.27P: Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis...

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Following is the structural formula of the tranquilizer meparfynol (Oblivon). Propose a synthesis for this compound starting with acetylene and a ketone. (Notice the -yn- and -ol in the chemical name of this compound, indicating that it contains alkyne and hydroxyl functional groups.)
One frequently used method for preparing methyl esters is by reaction of carboxylic acids with diazomethane, CH2N2. The reaction occurs in two steps: (l) protonation of diazomethane by the carboxylic acid to yield methyldiazonium ion, CH3N2+, plus a carboxylate ion; and (2) reaction of the carboxylate ion with CH3N2+. (a) Draw two resonance structures of diazomethane, and account for step 1. (b) What kind of reaction occurs in step 2?
Chrysanthemic acid occurs as a mixture of esters in flowers of the chrysanthemum (pyrethrum) family. Reduction of chrysanthemic acid to its alcohol followed by conversion of the alcohol to its tosylate gives chrysanthemyl tosylate. Solvolysis alcohols. of the tosylate gives a mixture of artemesia and yomogi HO НО Chrysanthemic acid Chrysanthemyl alcohol OH TsO DMSO Chrysanthemyl tosylate Artemesia alcohol Yomogi alcohol Propose a mechanism for the formation of these alcohols from chrysanthemyl tosylate.
H3C OH OH H+ CH3 Esters can be synthesized by an acid-catalyzed nucleophilic acyl substitution between an alcohol and a carboxylic acid; this process is called the Fischer esterification reaction. Because the alcohol oxygen is a poor nucleophile, the carbonyl carbon is made a better electrophile by protonation of the carbonyl oxygen. The steps of the synthesis are all reversible. The reaction is generally driven to completion by using an excess of the liquid alcohol as a solvent, or by distilling off the product as it forms. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CIX 10-4 H₂O CH3 H₂O CH3
>Nomex, a polyamide used in such applications as fire-retardant clothing, is prepared by reaction of 1,3-benzenediamine with 1,3-benzenedicarbonyl chloride. Show the structure of Nomex.
Give the major organic product(s) of the following reaction. 1) NABH4 ? 2) H3o+
H3C. H3C. CH3 nnc» XT :OH 2 CH₂OH HCI catalyst Aldehydes and ketones react reversibly with two equivalents of alcohol in the presence of an acid catalyst to give acetals. Alcohols are poor nucleophiles, and so protonation of the carbonyl oxygen is used to make the carbonyl carbon a stronger electrophile. Addition of the first equivalent of alcohol gives a hemiacetal, a hydroxyether. Addition of the second equivalent of alcohol is accompanied by loss of water to yield the product acetal. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 H3C CH3OH H3CQ OCH3 CH3 H3C. H HO: :OCH 3 CH3 46
Reaction of 1-butanol with periodane gives Butanal Propanoic acid 2-Butanone Butanoic acid as the major product.
21.95 A student carries out the following sequence of reactions. The IR and 1°C NMR spectra are shown for the product C. Draw structures for A-C. (Remember that the 13C NMR signal at 77 ppm is due to the CDCI3 solvent.) NaOC(CH)3 A (CH3)3COH 1. NaOEt, EtOH 1. NaOH, H,O C В 2. H,0º, A EtO OEt 2. Br(CH,),Br 100 90 80 70 60 – 50 40 - 30 20 C 4500 4000 3500 3000 2500 2000 1500 1000 500 200 175 150 125 100 75 50 25 Wavenumbers (cm-1) Chemical shift (ppm) % Transmittance
QII: Starting from toluene as the only organic reagent you have and use any other inorganic reagents to prepare: ОН CH3 Н,С CH3
Write the reagents used to synthesise the following compound starting from the benzoic acid CH3 'NH OH
When a compound like napihthalene C1oHa is dissolved in t-butyl methyl ether, then that solution is extracted with 3 M NaOH, and then the resulting basic aqueous layer is acidified with 6M HCI, what happens to the acidified aqueous layer? a) The naphthalene stays in the the aqueous layer as C10Ha O b) The naphthalene precipitates out as a solid, C10He O C) Nothing happens to the aqueous layer other than a dramatic raising of the pH d) The naphthalene stays in the aqueous layer as C10H>Na O e) Nothing happens to the aqueous layer other than a dramatic lowering of the pH O) The acid precipitates out as a solid, C10H>Na