Give the major organic product of each of the following...

Give the major organic product of each of the following reactions. Include stereochemistry where relevant. (a) dibutyl sulfide with 1 equivalent of $\mathrm{H}_{2} \mathrm{O}_{2}$ at $25^{\circ} \mathrm{C}$ (b) dibutyl sulfide with 2 or more equivalents of $\mathrm{H}_{2} \mathrm{O}_{2}$ and heat (c) cis-3-hexene with magnesium monoperoxyphthalate (MMPP) (d) the product of (c) with $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CuCNLi}_{2},$ then $\mathrm{H}_{3} \mathrm{O}^{+}$ (e) the product of (c) with solvent $\mathrm{H}_{2} \mathrm{O}$ in acidic solution (f) the product of (e) with periodic acid (g) the product of (d) with $\mathrm{NaH}$ in THF followed by $\mathrm{CH}_{3} \mathrm{I}$ (h) $(E)-3$ -methyl-3-hexene with $\mathrm{Hg}(\mathrm{OAc})_{2}$ in ethanol solvent followed by $\mathrm{NaBH}_{4}$ (i) the product of (h) with acidic methanol (j) $(R)$ -3-Methyl-1-bromopentane with $\mathrm{Mg}$ in ether, then with ethylene oxide, then with $\mathrm{CH}_{3} \mathrm{I}$

Give the major organic product of each of the following reactions. Include stereochemistry where relevant.
(a) dibutyl sulfide with 1 equivalent of $\mathrm{H}_{2} \mathrm{O}_{2}$ at $25^{\circ} \mathrm{C}$
(b) dibutyl sulfide with 2 or more equivalents of $\mathrm{H}_{2} \mathrm{O}_{2}$ and heat
(c) cis-3-hexene with magnesium monoperoxyphthalate (MMPP)
(d) the product of
(c) with $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CuCNLi}_{2},$ then $\mathrm{H}_{3} \mathrm{O}^{+}$
(e) the product of
(c) with solvent $\mathrm{H}_{2} \mathrm{O}$ in acidic solution
(f) the product of
(e) with periodic acid
(g) the product of (d) with $\mathrm{NaH}$ in THF followed by $\mathrm{CH}_{3} \mathrm{I}$
(h) $(E)-3$ -methyl-3-hexene with $\mathrm{Hg}(\mathrm{OAc})_{2}$ in ethanol solvent followed by $\mathrm{NaBH}_{4}$
(i) the product of (h) with acidic methanol
(j) $(R)$ -3-Methyl-1-bromopentane with $\mathrm{Mg}$ in ether, then with ethylene oxide, then with $\mathrm{CH}_{3} \mathrm{I}$

Key Concepts

Grignard Reaction with Epoxides

Grignard reagents are organometallic nucleophiles that can open epoxide rings to form extended carbon chains. The reaction typically proceeds via nucleophilic attack on the less hindered carbon of the epoxide, leading to the formation of an alkoxide, which upon workup yields an alcohol. This method is a key strategy for carbon backbone elongation and for the synthesis of complex molecules with multiple stereocenters.

Oxymercuration–Demercuration Reaction

Oxymercuration–demercuration is a two-step process that converts alkenes into alcohols or ethers without undergoing carbocation rearrangement. In the first step, an alkene reacts with mercury(II) acetate to form a mercurinium ion intermediate, which is then attacked by a nucleophilic solvent, often leading to Markovnikov addition. The intermediate is subsequently reduced with sodium borohydride to substitute the mercury with hydrogen, yielding the final functionalized product with controlled stereochemistry.

Deprotonation and Alkylation Reactions

This concept involves the removal of an acidic proton by a strong base (e.g., sodium hydride) to produce a nucleophilic species, typically an alkoxide or carbanion. The resulting anion can then react with an electrophilic alkyl halide (like methyl iodide) in an SN2 displacement reaction to form a new carbon–carbon or carbon–heteroatom bond. This strategy is a fundamental method in organic synthesis for forming carbon skeletons and introducing substituents.

Periodic Acid Cleavage of Vicinal Diols

Periodic acid is well-known for cleaving vicinal diols into two carbonyl compounds. This oxidative cleavage mechanism is useful for breaking carbon–carbon bonds in a controlled fashion. The reaction proceeds via the formation of a cyclic periodate intermediate and is an important tool for structural elucidation of diols as well as for synthetic applications where the cleavage of a diol moiety is desired.

Organometallic Epoxide Ring Opening

In this reaction family the nucleophilic attack of organometallic reagents (such as organocuprates) on epoxides leads to the cleavage of the strained three?membered ring and the formation of new carbon–carbon bonds. The reaction generally proceeds with regioselectivity dictated by the substitution pattern of the epoxide, and the stereochemical outcome is typically anti to the leaving oxygen, making this a valuable method for constructing complex molecules.

Epoxidation Reaction

Epoxidation is the process by which an alkene is converted into an epoxide, a three?membered cyclic ether, using peroxy compounds such as peracids or other peroxides. This reaction is widely used because it selectively transforms carbon–carbon double bonds into reactive cyclic ethers that can undergo further transformations. Stereoselectivity is an important aspect of epoxidation, as the stereochemistry of the alkene is typically preserved in the epoxide product.

Oxidation of Sulfides

This concept involves the transformation of sulfide functional groups into higher oxidation state species. With one equivalent of an oxidizing agent like hydrogen peroxide, a sulfide is typically oxidized to a sulfoxide. With excess oxidant and heat, the reaction can proceed further to produce a sulfone. This oxidation pattern is significant in synthetic organic chemistry for controlling the oxidation state and properties of sulfur-containing compounds.

Acid-Catalyzed Epoxide Ring Opening

Under acidic conditions, epoxides can be protonated to form a more electrophilic intermediate, which is then attacked by nucleophiles such as water. This acid-catalyzed ring opening generally follows Markovnikov-type regioselectivity, leading to the formation of diols with an anti-disposition of substituents due to backside attack. The reaction is widely utilized to achieve controlled rearrangement and functionalization of epoxides.

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