Provide the products and curved-arrow mechanism for the formation of these products: CH(subscript)3O^-+CH(subscript)3SH -> ????
To determine the products and the curved-arrow mechanism for the given reaction: CH₃O⁻ + CH₃SH, we first need to understand the reactants and their properties.
CH₃O⁻ is the methoxide ion, which is a strong nucleophile. It can attack electrophilic centers or undergo nucleophilic substitution reactions.
CH₃SH is methyl mercaptan, which is a thiol compound. Thiol compounds can undergo reactions with strong nucleophiles.
Now, let's break down the reaction and determine the products and the curved-arrow mechanism step-by-step:
Step 1: Nucleophilic attack on the electrophilic center:
The methoxide ion (CH₃O⁻) can act as a strong nucleophile and attack the sulfur atom in CH₃SH. This is an example of a nucleophilic substitution reaction. The nucleophile (CH₃O⁻) attacks the electrophile (CH₃S⁺).
CH₃O⁻ + CH₃SH ⟶ CH₃S⁺CH₃O⁻ (Step 1)
Step 2: Rearrangement and proton transfer:
In this step, the CH₃S⁺CH₃O⁻ intermediate undergoes rearrangement to generate the product. The oxygen atom bearing the negative charge (⁻O) grabs a proton from the adjacent carbon with a positive charge (⁺CH₃). This proton transfer forms a new C-O bond.
CH₃S⁺CH₃O⁻ ⟶ CH₃SCH₃ + HO⁻ (Step 2)
The final products of the reaction are CH₃SCH₃ (dimethyl sulfide) and HO⁻ (hydroxide ion).
Curved-arrow mechanism:
The curved arrows in the mechanism are used to represent the flow of electrons during the reaction. In step 1, the curved arrow connects the electron pair in the nucleophile (methoxide ion, CH₃O⁻) to the electrophilic sulfur center in CH₃SH. In step 2, the curved arrow shows the movement of a proton from the carbon center to the oxygen atom.
Overall Reaction:
CH₃O⁻ + CH₃SH ⟶ CH₃SCH₃ + HO⁻
To summarize, the products formed from the reaction of CH₃O⁻ and CH₃SH are dimethyl sulfide (CH₃SCH₃) and hydroxide ion (HO⁻).