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Chapter 17: Q41P (page 895)

Predict the products formed when m-cresol (m-methylphenol) reacts with

(a) NaOH and then ethyl bromide

(b) CH3 acetyl chloride, CH3COCI

(c) bromine in CCI4 in the dark

(d) excess bromine in CCI4 in the light

(e) sodium dichromate in H2SO4

(f) two equivalents of tert-butyl chloride and AICI3

Short Answer

Expert verified

A chemical reaction in which the functional group attached to the compound is replaced by an electrophile is known as an electrophilic substitution reaction.

Step by step solution

01

Electrophilic Substitution

A chemical reaction in which the functional group attached to the compound is replaced by an electrophile is known as an electrophilic substitution reaction.

02

Subpart (a) The reaction of m-cresol with NaOH and then ethyl bromide.

03

Subpart (b) The reaction of m-cresol with  CH3 acetyl chloride, CH3COCI .

04

Subpart (c) The reaction of m-cresol with bromine in  CCI4 in the dark

05

Subpart (d) The reaction of m-cresol with excess bromine in  CCI4 in the light

(e) sodium dichromate in H2SO4

(f) two equivalents of tert-butyl chloride and AICI4

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Most popular questions from this chapter

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.

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.

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

In Chapter 14, we saw that Agent Orange contains (2,4,5-trichlorophenoxy) acetic acid, called 2,4,5-T. This compound is synthesized by the partial reaction of 1,2,4,5-tetrachlorobenzene with sodium hydroxide, followed by a reaction with sodium chloroacetate, ClCH2CO2Na.

(a) Draw the structures of these compounds, and write equations for these reactions.

(b) One of the impurities in the Agent Orange used in Vietnam was 2,3,7,8-tetrachlorodibenzodioxin (2,3,7,8-TCDD), often incorrectly called “dioxin.” Propose a mechanism to show how 2,3,7,8-TCDD is formed in the synthesis of 2,4,5-T.

(c) Show how the TCDD contamination might be eliminated, both after the first step and on completion of the synthesis

Propose a mechanism for the aluminum chloride-catalyzed reaction of benzene with chlorine.
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