Question

Draw the main organic products of the reaction. Indicate the stereochemistry, including H's, at each stereocenter....

Draw the main organic products of the reaction. Indicate the stereochemistry, including H's, at each stereocenter. Omit byproducts such as salts or methanol.

Draw the main organic products of the reaction. Indicate the stereochemistry, including H's, at each stereocenter. Omit byproducts such as salts or methanol.

Concepts and reason

A reaction is given whose correct products needs to be drawn. Firstly, identify whether the reaction follow the substitution or elimination reaction and the write the product formed through each of the mechanism followed.

Fundamentals

Substitution reaction can be categorized as, ${{\rm{S}}_{\rm{N}}}1$ and ${{\rm{S}}_{\rm{N}}}2$ depending on the type of mechanism followed.

${{\rm{S}}_{\rm{N}}}1$ reaction is unimolecular nucleophilic substitution reaction which takes place between a haloalkane and a nucleophile. The reaction takes place in two steps through a carbocation intermediate and the reaction product are formed with both retention as well as inversion of configuration. Consider the following scheme of a ${{\rm{S}}_{\rm{N}}}1$ reaction:

In haloalkane, the order of reactivity for the ${{\rm{S}}_{\rm{N}}}1$ substitution reaction is, $3^\circ > 2^\circ > 1^\circ > {\rm{C}}{{\rm{H}}_3}$ like the stability of carbocation.

${{\rm{S}}_{\rm{N}}}2$ reaction is bimolecular nucleophilic substitution reaction which takes place between a haloalkane and a nucleophile. The reaction takes place in one step through a transition state. Consider the following scheme of a ${{\rm{S}}_{\rm{N}}}2$ reaction:

In haloalkane, the order of reactivity for the ${{\rm{S}}_{\rm{N}}}2$ substitution reaction is, $3^\circ < 2^\circ < 1^\circ < {\rm{C}}{{\rm{H}}_3}$ .

Similarly, elimination reaction can be categorized as, ${\rm{E}}1$ and ${\rm{E}}2$ depending on the type of mechanism followed.

• Elimination reaction can be classified as ${\rm{E - }}1$ and ${\rm{E - 2}}$ . In ${\rm{E - }}1$ elimination reaction the reaction completes in two steps and involves the formation of carbocation intermediate. In haloalkane, the order of reactivity for the ${\rm{E - }}1$ elimination is, $3^\circ > 2^\circ > 1^\circ > {\rm{C}}{{\rm{H}}_3}$ like the stability of carbocation.

• In E-2 elimination reaction the reaction takes place in one step through the formation of a transition state. In haloalkane, the order of reactivity for the ${\rm{E - 2}}$ elimination is, $3^\circ < 2^\circ < 1^\circ < {\rm{C}}{{\rm{H}}_3}$ .

Consider the given reactants as shown below:

As the given reactant is secondary alkyl halide, therefore, it can undergo both substitution and elimination reaction.

Write the product of the reaction formed through substitution mechanism.

Write the product of the reaction formed through substitution mechanism.

Ans:

Hence, the main product of the given reaction is as follows:

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