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Chapter 3: Problem 150

Which of the following will decompose \(\mathrm{NaHCO}_{3}\) solution with the liberation of \(\mathrm{CO}_{2}\) gas? (a) phenol (b) p-nitrophenol (c) \(\mathrm{p}\) -cresol (d) \(2,4,6\) -trinitrophenol

Short Answer

Expert verified
The compound that will decompose NaHCO₃ solution and liberate CO₂ gas is (d) 2,4,6-trinitrophenol. This is because it has the highest acidity among the given compounds (phenol, p-nitrophenol, p-cresol, 2,4,6-trinitrophenol), allowing it to provide a proton (H⁺) and react with NaHCO₃ to release CO₂ gas. Reaction: \(\mathrm{C}_{6}\mathrm{H}_{2}(\mathrm{NO}_{2})_{3}\mathrm{OH} + \mathrm{NaHCO}_{3} \rightarrow \mathrm{C}_{6}\mathrm{H}_{2}(\mathrm{NO}_{2})_{3}\mathrm{O}^{-}\mathrm{Na}^{+} + \mathrm{H}_{2}\mathrm{O} + \mathrm{CO}_{2}\)

Step by step solution

01

Understanding the given compounds and their acid-base nature

First, let's understand each compound and determine their acid-base nature: (a) Phenol: (\(\mathrm{C}_{6}\mathrm{H}_{5}\mathrm{OH}\)) has moderately acidic nature due to the presence of an \(\mathrm{OH}\) group. (b) p-nitrophenol: has a similar structure as phenol but has a nitro group (\(\mathrm{NO}_{2}\)) at the para position, increasing the acidity. (c) p-cresol: similar to phenol but with a methyl group (\(\mathrm{CH}_{3}\)) at the para position, which makes it slightly less acidic than phenol. (d) 2,4,6-trinitrophenol: has a phenol core with three nitro groups at the ortho and para positions, making it more acidic (a strong acid).
02

Comparing the relative acidity of the compounds

Based on the information above, the ranking of the compounds in terms of acidity is: 2,4,6-trinitrophenol > p-nitrophenol > phenol > p-cresol Higher-ranking acids can provide protons to react with the NaHCO₃ and liberate CO₂.
03

Choosing the compound to decompose NaHCO₃

From the ranking, 2,4,6-trinitrophenol has the highest acidity among the given compounds. Thus, 2,4,6-trinitrophenol would be the compound to liberate CO₂ gas by decomposing NaHCO₃. The reaction can be represented as: \(\mathrm{C}_{6}\mathrm{H}_{2}(\mathrm{NO}_{2})_{3}\mathrm{OH} + \mathrm{NaHCO}_{3} \rightarrow \mathrm{C}_{6}\mathrm{H}_{2}(\mathrm{NO}_{2})_{3}\mathrm{O}^{-}\mathrm{Na}^{+} + \mathrm{H}_{2}\mathrm{O} + \mathrm{CO}_{2}\) The correct answer is: (d) 2,4,6-trinitrophenol.

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Most popular questions from this chapter

$$ \begin{array}{l} \text { The organic product (X) formed in the following reaction is }\\\ \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{Cl}+\mathrm{C}_{6} \mathrm{H}_{5} \stackrel{\mathrm{AICl}_{3}}{\longrightarrow} \mathrm{X} \end{array} $$

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) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O} \mathrm{Na}+\mathrm{CH}_{3} \mathrm{Br} \longrightarrow\)

(Resorcinol) when heated with phthalic anhydride to about \(473 \mathrm{~K}\), the product formed is

When toluene and benzoic acid are subjected to Birch reduction separately, the products obtained, respectively, are

The C-O bond length in phenol is shorter compared to C-O bond length in alcohols. This is due to (a) the sp \(^{2}\) nature of the carbon of the phenol. (b) the delocalization of the electron density from the ring to the more electronegative oxygen. (c) the dipole distribution of the \(\mathrm{C}-\mathrm{O}\) bond in phenol with the oxygen at the negative end of the dipole. (d) the acidic nature of the phenolic hydrogen.
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