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Chapter 4: Problem 36

Write equations for the reaction of each compound with \(\mathrm{H}_{2} \mathrm{SO}_{4}\), a strong protic acid. (a) \(\mathrm{CH}_{3} \mathrm{OCH}_{3}\) (b) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SCH}_{2} \mathrm{CH}_{3}\) (c) \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3}\) (d) \(\mathrm{CH}_{3} \mathrm{CH}_{3}\) (f) \(\mathrm{CH}_{3} \mathrm{COCH}_{3}\)

Short Answer

Expert verified
Question: Write short equations for the reactions of the following compounds with H₂SO₄: 1. CH₃OCH₃ 2. CH₃CH₂SCH₂CH₃ 3. CH₃CH₂NHCH₂CH₃ 4. CH₃CH₃ 5. CH₃COCH₃ Answer: 1. CH₃OCH₃ + H₂SO₄ → CH₃OCH₃H⁺ + HSO₄⁻ 2. CH₃CH₂SCH₂CH₃ + H₂SO₄ → CH₃CH₂SCH₂CH₃H⁺ + HSO₄⁻ 3. CH₃CH₂NHCH₂CH₃ + H₂SO₄ → CH₃CH₂NHCH₂CH₃H⁺ + HSO₄⁻ 4. CH₃CH₃ + H₂SO₄ → No reaction 5. CH₃COCH₃ + H₂SO₄ → CH₃COCH₃H⁺ + HSO₄⁻

Step by step solution

01

Reaction of CH₃OCH₃ with H₂SO₄

The lone pair electrons on the oxygen atom in CH₃OCH₃ will react with the acidic hydrogen atom of H₂SO₄, forming a protonated ether, which is an intermediate. The reaction will be: \(\mathrm{CH}_{3} \mathrm{OCH}_{3} + \mathrm{H}_{2} \mathrm{SO}_{4} \rightarrow \mathrm{CH}_{3} \mathrm{OCH}_{3}\mathrm{H}^{+} + \mathrm{HSO}_{4}^{-}\)
02

Reaction of CH₃CH₂SCH₂CH₃ with H₂SO₄

The sulfur atom in CH₃CH₂SCH₂CH₃ has lone pair electrons and is nucleophilic. It will react with the acidic hydrogen atom of H₂SO₄, forming an intermediate thioether. The reaction will be: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SCH}_{2} \mathrm{CH}_{3} + \mathrm{H}_{2} \mathrm{SO}_{4} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{SCH}_{2} \mathrm{CH}_{3}\mathrm{H}^{+} + \mathrm{HSO}_{4}^{-}\)
03

Reaction of CH₃CH₂NHCH₂CH₃ with H₂SO₄

The nitrogen atom in CH₃CH₂NHCH₂CH₃ has lone pair electrons and is nucleophilic. It will react with the acidic hydrogen atom of H₂SO₄, forming an intermediate amine. The reaction will be: \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3} + \mathrm{H}_{2} \mathrm{SO}_{4} \rightarrow \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NHCH}_{2} \mathrm{CH}_{3}\mathrm{H}^{+} + \mathrm{HSO}_{4}^{-}\)
04

Reaction of CH₃CH₃ with H₂SO₄

There are no nucleophilic atoms in \(\mathrm{CH}_{3} \mathrm{CH}_{3}\), so there will be no direct reaction with H₂SO₄. Hence, the equation is: \(\mathrm{CH}_{3} \mathrm{CH}_{3} + \mathrm{H}_{2} \mathrm{SO}_{4} \rightarrow\) No reaction
05

Reaction of CH₃COCH₃ with H₂SO₄

The oxygen atom in the carbonyl group of CH₃COCH₃ has lone pair electrons and is nucleophilic. It will react with the acidic hydrogen atom of H₂SO₄, forming a protonated ketone, an intermediate. The reaction will be: \(\mathrm{CH}_{3} \mathrm{COCH}_{3} + \mathrm{H}_{2} \mathrm{SO}_{4} \rightarrow \mathrm{CH}_{3} \mathrm{COCH}_{3}\mathrm{H}^{+} + \mathrm{HSO}_{4}^{-}\)

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Most popular questions from this chapter

Following is a structural formula for the tert-butyl cation. (We discuss the formation, stability, and reactions of cations such as this one in Chapter 6 .) C[C+](C)C tert-Butyl cation (a carbocation) (a) Predict all \(\mathrm{C}-\mathrm{C}-\mathrm{C}\) bond angles in this cation. (b) What is the hybridization of the carbon bearing the positive charge? (c) Write a balanced equation to show its reaction as a Lewis acid with water. (d) Write a balanced equation to show its reaction as a Brønsted-Lowry acid with water.

Which has the larger numerical value? (a) The \(\mathrm{p} K_{\mathrm{a}}\) of a strong acid or the \(\mathrm{p} K_{\mathrm{a}}\) of a weak acid (b) The \(K_{\mathrm{a}}\) of a strong acid or the \(K_{\mathrm{a}}\) of a weak acid

Methyl isocyanate, \(\mathrm{CH}_{3}-\mathrm{N}=\mathrm{C}=\mathrm{O}\), is used in the industrial synthesis of a type of pesticide and herbicide known as a carbamate. As a historical note, an industrial accident in Bhopal, India, in 1984 resulted in leakage of an unknown quantity of this chemical into the air. An estimated 200,000 persons were exposed to its vapors, and over 2000 of these people died. (a) Write a Lewis structure for methyl isocyanate, and predict its bond angles. What is the hybridization of its carbonyl carbon? Of its nitrogen atom? (b) Methyl isocyanate reacts with strong acids, such as sulfuric acid, to form a cation. Will this molecule undergo protonation more readily on its oxygen or nitrogen atom? In considering contributing structures to each hybrid, do not consider structures in which more than one atom has an incomplete octet.

Account for the fact that nitroacetic acid, \(\mathrm{O}_{2} \mathrm{NCH}_{2} \mathrm{COOH}\left(\mathrm{p} K_{\mathrm{a}} 1.68\right)\), is a considerably stronger acid than acetic acid, \(\mathrm{CH}_{3} \mathrm{COOH}\left(\mathrm{p} K_{\mathrm{a}} 4.76\right)\).

Explain why the hydronium ion, \(\mathrm{H}_{3} \mathrm{O}^{+}\), is the strongest acid that can exist in aqueous solution. What is the strongest base that can exist in aqueous solution?
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