Chapter 23: Problem 590
Suggest a mechanism for the steps in the synthesis of phenolphthalein.
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Chapter 23: Problem 590
Suggest a mechanism for the steps in the synthesis of phenolphthalein.
These are the key concepts you need to understand to accurately answer the question.
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Write structural formulas for substances (one for each part) that fit the following descriptions: (a) a phenol that would be a stronger acid than phenol itself (b) that isomer of dichlorophenol that is the strongest acid (c) the Claisen rearrangement product from a \(\alpha\) -methylally1 2,6 -dimethylpheny 1 ether (d) a quinone which does not undergo Diels-Alder addition (e) a quinone that would be a better charge-transfer agent than quinone itself.
Aspirin is acetylsalicylic acid (o-acetoxybenzoic acid, \(\left.0-\mathrm{CH}_{3} \mathrm{COO}-\mathrm{C}_{6} \mathrm{H}_{4} \mathrm{COOH}\right)\); oil of wintergreen is the ester, methyl salicylate. Outline the synthesis of these two compounds from phenol.
2, 4-Dichlorophenoxyacetic acid is the important weed-killer known as \(2,4-\mathrm{D}\). Outline the synthesis of this compound starting from benzene or toluene and acetic acid.
How much difference in physical properties would you expect for o-and \(p\) -cyanophenol isomers? Explain.
Tropolone \(\left(\mathrm{I}, \mathrm{C}_{7} \mathrm{H}_{7} \mathrm{O}_{2}\right)\) has a flat molecule with all carbon-carbon bonds of the same length (1.40 A). The measured heat of combustion is \(20 \mathrm{kcal}\) lower than that calculated by the method of summing bond energies. Its dipole moment is \(3.71 \mathrm{D}\); that of 5-bromotropolone is \(2.07 \mathrm{D}\). Tropolone undergoes the Reimer-Tiemann reaction, couples with diazonium ions, and is nitrated by dilute nitric acid. It gives a green color with ferric chloride, and does not react with 2,4 -dinitrophenylhydrazine. Tropolone is both acidic \(\left(\mathrm{K}_{\mathrm{a}}=10^{-7}\right)\) and weakly basic, forming a hydrochloride in ether. (a) What class of compounds does tropolone resemble? Is it adequately represented by formula I? (b) Using both valence-bond and orbital structures, account for the properties of tropolone. (c) In what direction is the dipole moment of tropolone? Is this consistent with the structure you have proposed? (d) The infrared spectrum of tropolone shows a broad band at about \(3150 \mathrm{~cm}^{-1}\) that changes only slightly upon dilution. What does this tell you about the structure of tropolone?
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