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Chapter 20: Problem 475

What carboxylic acid can be prepared from p-Bromotoluene: (a) by direct oxidation? (b) by free-radical chlorination followed by the nitrile synthesis?

Short Answer

Expert verified
(a) p-Bromobenzoic acid can be prepared from p-Bromotoluene by direct oxidation. (b) p-Bromobenzoic acid can also be prepared from p-Bromotoluene by free-radical chlorination followed by nitrile synthesis.

Step by step solution

01

Direct oxidation of p-Bromotoluene

To find the carboxylic acid obtained by direct oxidation of p-Bromotoluene, we need to oxidize the methyl group attached to the benzene ring. Here, we will use potassium permanganate (KMnO4) as the oxidizing agent, which will oxidize the methyl group to a carboxyl group (-COOH). The resulting carboxylic acid will have the carboxyl group in the same position as the original methyl group: \(p-Bromotoluene \xrightarrow[KMnO4]{oxidation} p-Bromobenzoic \; acid \) (a) p-Bromobenzoic acid can be prepared from p-Bromotoluene by direct oxidation.
02

Free-radical chlorination of p-Bromotoluene

In this step, we will perform a free-radical chlorination on p-bromotoluene. In this reaction, a hydrogen from the methyl group gets replaced by a chlorine atom, forming a chlorinated product. \(p-Bromotoluene \xrightarrow[Cl2, h\nu]{free\;radical\;chlorination} p-Bromo\;chlorotoluene\)
03

Nitrile synthesis of p-Bromo chlorotoluene

Now, we need to convert p-Bromochlorotoluene into a nitrile group by substitution reaction using a cyanide ion (CN-). This will replace the chlorine atom present in the p-Bromochlorotoluene with a nitrile group (-CN). \(p-Bromo\;chlorotoluene \xrightarrow[KCN]{Substitution} p-Bromo\;benzonitrile\)
04

Hydrolysis of p-Bromo benzonitrile

Finally, we need to convert the nitrile group (-CN) into a carboxyl group (-COOH). To do this, we will perform a hydrolysis reaction on p-Bromo benzonitrile using an acid or base catalyst. \(p-Bromo\;benzonitrile \xrightarrow[H3O+/OH-]{Hydrolysis} p-Bromobenzoic\;acid\) (b) p-Bromobenzoic acid can be prepared from p-Bromotoluene by free-radical chlorination followed by nitrile synthesis.

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Most popular questions from this chapter

Explain why decarboxylation of \(a, \alpha\) -dimethylacetoacetic acid, \(\mathrm{CH}_{3} \mathrm{COC}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CO}_{2} \mathrm{H}\), in the presence of bromine gives \(\alpha\) -bromoisopropyl methy 1 ketone, \(\mathrm{CH}_{3} \mathrm{COC}\left(\mathrm{CH}_{3}\right)_{2} \mathrm{Br}\).

At \(110^{\circ}\) and \(454 \mathrm{~mm}\) pressure, \(0.11 \mathrm{~g}\) acetic acid vapor occupies \(63.7 \mathrm{cc}\); at \(156^{\circ}\) and \(458 \mathrm{~mm}, 0.081\) g occupies \(66.4 \mathrm{cc}\). Calculate the molecular weight of acetic acid in the vapor phase at each temperature. How do you interpret these results?

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