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Chapter 17: Q68P (page 910)

When 1,2-dibromo-3,5-dinitrobenzene is treated with excess NaOH at 50 °C, only one of the bromine atoms is replaced. Draw an equation for this reaction, showing the product you expect. Give a mechanism to account for the formation of your proposed product.

Short Answer

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Formation of 1-Bromo-2-hydroxy-3,5-dinitrobenzene

Step by step solution

01

Reaction of 1,2-dibromo-3,5-dinitrobenzene

The equation for the reaction of 1,2-dibromo-3,5—dinitrobenzene with excess NaOH at forms 1-Bromo-2-hydroxy-3,5 dinitrobenzene as the only product.

Formation of 1-Bromo-2-hydroxy-3,5-dinitrobenzene

02

Mechanism for the reaction

The bromide at 2-position is replaced by a hydroxy group, this is because in this case the reaction intermediate gets stabilized by two nitro groups. But in the case of 1-Bromo, such stabilization does not arise because it is meta to both nitro groups.

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Most popular questions from this chapter

Predict the site(s) of electrophilic attack on these compounds.

(a)

(b)

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

Reagents Desired Product

(a) benzene + n-butyl bromide n-butylbenzene

(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene

(c) bromobenzene + ethyl chloride p-bromoethylbenzene

(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide

(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)

Phenolphthalein, a common nonprescription laxative, is also an acid-base indicator that is colorless in acid and red in base. Phenolphthalein is synthesized by the acid-catalyzed reaction of phthalic anhydride with 2 equivalents of phenol.

(a) Propose a mechanism for the synthesis of phenolphthalein.

(b) Propose a mechanism for the conversion of phenolphthalein to its red dianion in the base.

(c) Use resonance structures to show that the two phenolic oxygen atoms are equivalent (each with half a negative charge) in the red phenolphthalein dianion.


Phthalic anhydride Phenolphthalein red dianion

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

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.
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