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Chapter 18: 4P (page 683)

Draw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form a substituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that can be used as a synthetic detergent to clean away dirt (see Problem 3.22).

Short Answer

Expert verified

The reactions in which the hydrogen atom of the benzene ring is replaced by a sulfonic acid functional groupSO3H .

Step by step solution

01

Aromatic sulphonation reaction

The reactions in which the hydrogen atom of the benzene ring is replaced by a sulfonic acid functional groupSO3H .

02

Formation of SO3+H  using  H2SO4

The generation ofSO3+Hfrom H2SO4is shown below.

03

Sulfonation of the given compound

The mechanism for the sulfonation of A is provided below

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Most popular questions from this chapter

Question: Use the reactions in this chapter along with those learned in Chapters 11 and 12 to synthesize each compound. You may use benzene, acetylene, two-carbon alcohols, ethylene oxide and any organic reagents.

d.

Draw the products formed when each compound is treated with HNO3 and H2SO4. State whether the reaction occurs faster or slower than a similar reaction with benzene.

Classify each substituent as electron donating or electron withdrawing.

Question: Carboxylic acid X is an intermediate in the multistep synthesis of proparacaine, a local anesthetic. Devise a synthesis of X from phenol and any needed organic or inorganic reagents.

Draw the products of each reaction

a)

b)

c)
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