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Chapter 17: Q49P (page 899)

Starting from toluene, propose a synthesis of this trisubstituted benzene

Short Answer

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A chemical reaction in which one functional group in a chemical compound replaced another functional group.is known as substitution reaction. It is classified into two types i.e, electrophilic substitution reaction and nucleophilic substitution reaction.

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01

Substitution Reaction

A chemical reaction in which one functional group in a chemical compound replaced another functional group.is known as substitution reaction. It is classified into two types i.e, electrophilic substitution reaction and nucleophilic substitution reaction.

02

Synthesis of trisubstituted benzene from toluene

By sulphonation of toluene we can substitute SO3H to the para position of the benzene ring as methyl is a ortho, para directing group.SO3H is a meta director. Then by the addition of nitric acid we can substitute nitro group to the ring at the ortho position.

Then by permanganate oxidation we can add 鈥揅OOH group in place of methyl group.

We have to removeSO3H from the compound to get the desired product. And nitro group can be reduced to amino group to obtain the final product.

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Most popular questions from this chapter

When anthracene is added to the reaction of chlorobenzene with concentrated NaOH at 350 掳C, an interesting Diels鈥揂lder adduct of the formula C20H14results. The proton NMR spectrum of the product shows a singlet of area 2 around d 3 and a broad singlet of area 12 around d 7. Propose a structure for the product, and explain why one of the aromatic rings of anthracene reacted as a diene.

Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.

Predict the major products of treating the following compounds with hot, concentrated potassium permanganate, followed by acidification with dilute HCl.

(a) isopropylbenzene

(b) p-xylene

(c) tetralin

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case, it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction

Indane can undergo free-radical chlorination at any of the alkyl positions on the aliphatic ring.

indane

  1. Draw the possible monochlorinated products from this reaction.
  2. Draw the possible dichlorinated products from this reaction.
  3. What instrumental technique would be most helpful for determining how many products are formed, and how many of those products are monochlorinated and how many are dichlorinated?
  4. Once the products have been separated, what instrumental technique would be most helpful for determining the structures of all the dichlorinated products?
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