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3C. 2-methyl-2-propanol (0.0100 mol) is reacted with NH4Br (0.0175 mol) and NH4Cl (0.0350 mol) in the presence of H₂SO4 (0.100 mol). What is the expected ratio of the products 2-bromo-2-methylpropane and 2-chloro-2-methylpropane? Explain your answer.

3C. 2-methyl-2-propanol (0.0100 mol) is reacted with NH4Br (0.0175 mol) and NH4Cl (0.0350 mol) in the presence of H₂SO4 (0.100 mol). What is the expected ratio of the products 2-bromo-2-methylpropane and 2-chloro-2-methylpropane? Explain your answer.

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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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### Chemical Reaction: 2-Methyl-2-Propanol with Ammonium Halides In this reaction, 2-methyl-2-propanol is undergoing substitution in the presence of sulfuric acid (H₂SO₄) with ammonium bromide (NH₄Br) and ammonium chloride (NH₄Cl). ### Problem Statement: 3C. 2-methyl-2-propanol (0.0100 mol) is reacted with NH₄Br (0.0175 mol) and NH₄Cl (0.0350 mol) in the presence of H₂SO₄ (0.100 mol). What is the expected ratio of the products 2-bromo-2-methylpropane and 2-chloro-2-methylpropane? **Explain your answer.** ### Detailed Explanation: 1. **Reaction Overview:** - **Initial substances:** - 2-methyl-2-propanol (C₄H₁₀O) - Ammonium bromide (NH₄Br) - Ammonium chloride (NH₄Cl) - Sulfuric acid (H₂SO₄) - **Products formed:** - 2-bromo-2-methylpropane (C₄H₉Br) - 2-chloro-2-methylpropane (C₄H₉Cl) 2. **Mechanism:** - Sulfuric acid (H₂SO₄) acts as a strong acid, protonating the 2-methyl-2-propanol to form a more reactive intermediate. - This intermediate can then undergo substitution reactions with bromide ions (\(Br^{-}\)) and chloride ions (\(Cl^{-}\)) present in the solution. 3. **Molar Ratios:** - Moles of 2-methyl-2-propanol: \( 0.0100 \) mol - Moles of NH₄Br providing bromide ions: \( 0.0175 \) mol - Moles of NH₄Cl providing chloride ions: \( 0.0350 \) mol 4. **Reaction Conditions and Predictions:** - The reaction is likely to proceed via an \( S_N1 \) mechanism due to the tertiary alcohol (2-methyl-2-propanol),
Transcribed Image Text:### Chemical Reaction: 2-Methyl-2-Propanol with Ammonium Halides In this reaction, 2-methyl-2-propanol is undergoing substitution in the presence of sulfuric acid (H₂SO₄) with ammonium bromide (NH₄Br) and ammonium chloride (NH₄Cl). ### Problem Statement: 3C. 2-methyl-2-propanol (0.0100 mol) is reacted with NH₄Br (0.0175 mol) and NH₄Cl (0.0350 mol) in the presence of H₂SO₄ (0.100 mol). What is the expected ratio of the products 2-bromo-2-methylpropane and 2-chloro-2-methylpropane? **Explain your answer.** ### Detailed Explanation: 1. **Reaction Overview:** - **Initial substances:** - 2-methyl-2-propanol (C₄H₁₀O) - Ammonium bromide (NH₄Br) - Ammonium chloride (NH₄Cl) - Sulfuric acid (H₂SO₄) - **Products formed:** - 2-bromo-2-methylpropane (C₄H₉Br) - 2-chloro-2-methylpropane (C₄H₉Cl) 2. **Mechanism:** - Sulfuric acid (H₂SO₄) acts as a strong acid, protonating the 2-methyl-2-propanol to form a more reactive intermediate. - This intermediate can then undergo substitution reactions with bromide ions (\(Br^{-}\)) and chloride ions (\(Cl^{-}\)) present in the solution. 3. **Molar Ratios:** - Moles of 2-methyl-2-propanol: \( 0.0100 \) mol - Moles of NH₄Br providing bromide ions: \( 0.0175 \) mol - Moles of NH₄Cl providing chloride ions: \( 0.0350 \) mol 4. **Reaction Conditions and Predictions:** - The reaction is likely to proceed via an \( S_N1 \) mechanism due to the tertiary alcohol (2-methyl-2-propanol),
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