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🥼organic chemistry review

Dimethyl Sulfide

Written by the Fiveable Content Team • Last updated September 2025
Written by the Fiveable Content Team • Last updated September 2025

Definition

Dimethyl sulfide is a colorless, flammable, and volatile organic compound with a strong, unpleasant odor. It is an important chemical species that is commonly encountered in various organic chemistry contexts, including the oxidation of alkenes, the oxidative cleavage of alkynes, and the preparation of aldehydes and ketones.

5 Must Know Facts For Your Next Test

  1. Dimethyl sulfide is a byproduct of the oxidation of alkenes, where the carbon-carbon double bond is cleaved to form two carbonyl compounds.
  2. In the oxidative cleavage of alkynes, dimethyl sulfide can be used as a reducing agent to convert the alkyne to a carbonyl compound.
  3. Dimethyl sulfide is a common precursor in the preparation of aldehydes and ketones, as it can be oxidized to form these important carbonyl compounds.
  4. The unpleasant odor of dimethyl sulfide is due to its sulfur-containing nature, which can be detected at very low concentrations.
  5. Dimethyl sulfide is found naturally in various environments, including the ocean, where it is produced by the decomposition of organic matter.

Review Questions

  • Explain the role of dimethyl sulfide in the oxidation of alkenes and the subsequent cleavage to carbonyl compounds.
    • In the oxidation of alkenes, the carbon-carbon double bond is cleaved, resulting in the formation of two carbonyl compounds. Dimethyl sulfide is a byproduct of this reaction, as it is formed when the alkene is oxidized. The presence of dimethyl sulfide in this context indicates that the oxidation of the alkene has occurred, leading to the production of the desired carbonyl compounds.
  • Describe how dimethyl sulfide can be used in the oxidative cleavage of alkynes to prepare carbonyl compounds.
    • Dimethyl sulfide can act as a reducing agent in the oxidative cleavage of alkynes. In this process, the alkyne is first oxidized, and then dimethyl sulfide is used to reduce the resulting carbonyl compounds. This allows for the conversion of the alkyne to the desired carbonyl compounds, with dimethyl sulfide playing a crucial role in the overall reaction.
  • Analyze the importance of dimethyl sulfide in the preparation of aldehydes and ketones, and explain how its oxidation can lead to the formation of these carbonyl compounds.
    • Dimethyl sulfide is a common precursor in the preparation of aldehydes and ketones. When dimethyl sulfide is oxidized, it can be converted into these important carbonyl compounds. The oxidation of dimethyl sulfide involves the breaking of the carbon-sulfur bonds, which allows for the formation of the desired aldehydes and ketones. This makes dimethyl sulfide a valuable starting material in the synthesis of these carbonyl compounds, which are widely used in organic chemistry and various industrial applications.