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Chapter 16: Q 4P (page 486)

Question: When benzene is treated with D2SO4, deuterium slowly replaces all six hydrogens in the aromatic ring. Explain.

Short Answer

Expert verified

Aromatic sulphonation is done by reacting the aromatic ring with a mixture of H2SO4and SO3.The reactive electrophile is HSO3+or SO3neutral based on the reaction conditions. Sulfonation happens in the presence of strong acid.

Step by step solution

01

Aromatic sulfonation

Aromatic sulphonation is done by reacting the aromatic ring with a mixture of H2SO4and SO3.The reactive electrophile is HSO3+or SO3neutral based on the reaction conditions. Sulfonation happens in the presence of strong acid.

02

Step 2: Treatment of benzene with D2SO4

Benzene can be protonated by strong acids. The resulting intermediate loses either deuterium or hydrogen. If hydrogen is lost, deuterated benzene is formed as the product. The attack by deuterium happens at all positions and leads to the replacement of all hydrogens by deuterium. The reaction can be shown as:

Reaction of Benzene withD2SO4

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Most popular questions from this chapter

The nitroso group, - NO, is one of the few non-halogens that is an ortho- and para-directing deactivator. Explain this behaviour by drawing resonance structures of the carbocation intermediates in ortho, meta, and para electrophilic reaction on nitroso benzene,C6H5N=O.

p-Bromotoluene reacts with potassium amide to give a mixture of m and p-methylaniline. Explain.

The carbocation electrophile in a Friedel–Crafts reaction can be generated by an alternate means than reaction of an alkyl chloride with. For example, reaction of benzene with 2-methylpropene in the presence of H3PO4 yields tert-butylbenzene. Propose a mechanism for this reaction.

Using resonance structures of the intermediates, explain why bromination of biphenyl occurs at ortho and para positions rather than at meta.

Rank the following aromatic compounds in the expected order of their

reactivity toward Friedel–Crafts alkylation. Which compounds are

unreactive?

(a)Bromobenzene (b) Toluene (c) Phenol

(d)Aniline (e)Nitrobenzene (f)p-Bromotoluene
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