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Chapter 18: 20 P (page 702)

Draw the products of each reaction.

Short Answer

Expert verified

Phenol is an ortho-para directing group due to the maximum electron density at ortho and para positions. In the presence of Lewis acid, a trichloro compound is formed.

Step by step solution

01

Phenol

Phenol is an ortho-para directing group due to the maximum electron density at ortho and para positions. In the presence of Lewis acid, a trichloro compound is formed.

02

OH as ortho-para directing group

The OH group has a lone pair of electrons which it donates to the benzene ring to create maximum electron density. The delocalization of electrons is maximum at ortho and para positions.

03

Explanation

a. The chlorination of phenol in the presence of Lewis acid gives trichlorophenol, as shown below.

b. The substituent on the benzene ring is OH which is electron-donating. The chlorination of phenol gives ortho and para chlorophenol due to the maximum electron density at these positions.


c. Toluene is also an electron-rich compound, but the methyl group is a sigma donor. It donates its electrons to the ring slower than the OH group in phenol.

Therefore, in the presence of Lewis acid, ortho and para products are formed.

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Most popular questions from this chapter

Question: The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown.

a. Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole.

b. Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline.

c. Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.

Draw the products formed when phenol ( C6H5OH) is treated with each set of reagents.

a. [1] HNO3, H2SO4; [2] Sn, HCl

b. [1] CH3CH22COCl,AlCl3; [2] Zn(Hg), HCl

c. [1] CH3CH2Cl,AlCl3; [2]Br2,hν

d. [1] CH32CHCl,AlCl3; [2] KMnO4

Question: Explain the reactivity and orientation effects observed in each heterocycle.

a. Pyridine is less reactive than benzene in electrophilic aromatic substitution and yields 3-substituted products.

b. Pyrrole is more reactive than benzene in electrophilic aromatic substitution and yields 2-substituted products.

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.

For each N-substituted benzene, predict whether the compound reacts faster than, slower than, or at a similar rate to benzene in electrophilic aromatic substitution. Then draw the major product (s) formed when each compound reacts with a general electrophile E+.
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