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Chapter 3: Problem 86

The carboxyl group is displaced when salicylic acid undergoes (a) bromination (b) nitration (c) either (a) or (b) (d) dehydration

Short Answer

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(a) Bromination (b) Nitration (c) Dehydration (d) Hydration Answer: (c) Dehydration

Step by step solution

01

Recall the structure of salicylic acid

Salicylic acid contains a carboxylic group (--COOH), which is attached to a benzene ring with a hydroxyl group (--OH) at the adjacent position. It is essential to recall the structure to understand its reactions.
02

Analyze carboxyl group reaction in Bromination

Bromination refers to the addition of bromine to an organic compound. When salicylic acid undergoes bromination, the benzene ring is substituted, typically at the ortho or para positions with respect to the hydroxyl group. The carboxyl group remains unaffected (i.e., it is not displaced) during the bromination reaction.
03

Analyze carboxyl group reaction in Nitration

Nitration is the addition of a nitro group (-NO2) to an organic compound. When salicylic acid undergoes nitration, a nitro group is introduced ortho and para to the hydroxyl group in the benzene ring. The carboxyl group in salicylic acid is not displaced during nitration.
04

Analyze carboxyl group reaction in Dehydration

Dehydration refers to the removal of a water molecule from a compound. Since the functional group in question is the carboxyl group, when salicylic acid undergoes dehydration, the carboxyl group loses a hydroxyl group (-OH) and becomes a carbonyl group (--C=O). In this case, the carboxyl group is displaced.
05

Choose the correct answer

Based on the analysis above, the carboxyl group in salicylic acid is displaced when the compound undergoes dehydration. Therefore, the correct answer is (d) dehydration.

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Most popular questions from this chapter

Anisole is not formed in the reaction (a) phenol \(+\mathrm{CH}_{3} \mathrm{Br} \stackrel{\mathrm{NaOH}}{\longrightarrow}\) (c) phenol \(+\left(\mathrm{CH}_{3}\right)_{2} \mathrm{SO}_{4} \stackrel{\mathrm{NaOH}}{\longrightarrow}\)

The major product formed by the reaction of \(\mathrm{N}\) -phenylbenzamide with \(\mathrm{Br}_{2} / \mathrm{Fe}\) is

Column I Column II (a) Electrophilic substitution (p) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~N}_{2} \mathrm{Cl}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH} \stackrel{\mathrm{NaOH}}{\longrightarrow}\) (b) Nucleophilic substitution (q) Toluene + \(\mathrm{NBS} \longrightarrow\) (c) Free radical substitution (r) Dow's process (d) Coupling reaction (s) Phenol \(\longrightarrow\) picric acid (t) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O} \mathrm{Na}+\mathrm{CH}_{3} \mathrm{Br} \longrightarrow\)

Column I \(\quad\) Column II (a) \(\mathrm{C}_{6} \mathrm{H}_{6}+\mathrm{CH}_{3}-\mathrm{CH}=\mathrm{CH}_{2} \stackrel{\mathrm{H}_{2} \mathrm{SO}_{4}}{\longrightarrow}\) (p) Schotten-Baumann reaction (b) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{COCl} \stackrel{\mathrm{NaOH}}{\longrightarrow}\) (q) Friedel-Crafts reaction (c) \(\mathrm{C}_{6} \mathrm{H}_{6}+\stackrel{\mathrm{AlCl}_{3}}{\longrightarrow}\) (r) Reimer-Tiemann reaction (d) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH} \frac{{ }_{5}^{(\mathrm{i}) \mathrm{CCl}_{4} / \mathrm{NaOH}}}{{ }_{(\text {iii }) \mathrm{H}_{3} \mathrm{O}^{+}}}{\longrightarrow}\) (s) Isopropyl benzene (t) Electrophilic substitution

Identify the wrong statement among the following related to phenol. (a) Phenol is a weaker acid than carbonic acid. (b) When distilled with zinc, phenol gives benzene. (c) Among the three isomers of nitrophenol, the one that is least soluble in water is \(\mathrm{p}\) -nitrophenol. (d) Formation of phenol from chlorobenzene is an example of nucleophilic aromatic substitution.
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