Question

Write equations for the reaction of each compound with $\mathrm{H}_{2} \mathrm{SO}_{4}$, 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) \(\mathrm{CH}_{3} \mathrm{NCH}_{3}\) (e) \(\mathrm{CH}_{3}{ }_{\mathrm{C} C H}^{3}\)

Short answer

Question: Write the balanced chemical equation when the following compounds react with sulfuric acid (H₂SO₄): a) Methoxy methane (CH₃OCH₃) b) Ethyl methyl sulfide (CH₃CH₂SCH₂CH₃) c) N-ethyl methanamide (CH₃CH₂NHCH₂CH₃) d) Dimethyl amine (CH₃NCH₃) e) 2-methylpropene (CH₃C≡CH*CH₃) Answer: a) CH₃OCH₃ + H₂SO₄ -> CH₃OCH₃H⁺ + HSO₄⁻ b) CH₃CH₂SCH₂CH₃ + H₂SO₄ -> CH₃CH₂SCH₃H⁺ + HSO₄⁻ c) CH₃CH₂NHCH₂CH₃ + H₂SO₄ -> CH₃CH₂NHCH₂CH₃H⁺ + HSO₄⁻ d) CH₃NCH₃ + H₂SO₄ -> CH₃NHCH₃H⁺ + HSO₄⁻ e) CH₃C≡CH*CH₃ + H₂SO₄ -> CH₃C≡CH-C*H₂CH₃ + HSO₄⁻

Step-by-step solution

Identify the Reaction Site

First, we need to identify the reaction site where protonation can occur. In this case, oxygen in CH₃OCH₃ can be protonated, as it is electronegative, and will be attracted to the positive hydrogen ion in H₂SO₄.

Writing the reaction

CH₃OCH₃ + H₂SO₄ -> CH₃OCH₃H⁺ + HSO₄⁻ (b) Reaction of ethyl methyl sulfide (CH₃CH₂SCH₂CH₃) with H₂SO₄

Identify the Reaction Site

In this case, sulfur in CH₃CH₂SCH₂CH₃ can be protonated, as it is electronegative, and will be attracted to the positive hydrogen ion in H₂SO₄.

Writing the reaction

CH₃CH₂SCH₂CH₃ + H₂SO₄ -> CH₃CH₂SCH₃H⁺ + HSO₄⁻ (c) Reaction of N-ethyl methanamide (CH₃CH₂NHCH₂CH₃) with H₂SO₄

Identify the Reaction Site

In this case, nitrogen in CH₃CH₂NHCH₂CH₃ can be protonated, as it is electronegative, and will be attracted to the positive hydrogen ion in H₂SO₄.

Writing the reaction

CH₃CH₂NHCH₂CH₃ + H₂SO₄ -> CH₃CH₂NHCH₂CH₃H⁺ + HSO₄⁻ (d) Reaction of dimethyl amine (CH₃NCH₃) with H₂SO₄

Identify the Reaction Site

In this case, nitrogen in CH₃NCH₃ can be protonated, as it is electronegative, and will be attracted to the positive hydrogen ion in H₂SO₄.

Writing the reaction

CH₃NCH₃ + H₂SO₄ -> CH₃NHCH₃H⁺ + HSO₄⁻ (e) Reaction of 2-methylpropene (CH₃C≡CH*CH₃) with H₂SO₄

Identify the Reaction Site

In this case, the carbon atom in the triple bond can be protonated, as it has a partial negative charge due to its π-electrons, and will be attracted to the positive hydrogen ion in H₂SO₄.

Writing the reaction

CH₃C≡CH * CH₃ + H₂SO₄ -> CH₃C≡CH-C*H₂CH₃ + HSO₄⁻