Question

# Draw the major organic product of the reaction. Show the stereochemistry, if applicable. Omit byproducts such as wate...

Draw the major organic product of the reaction. Show the stereochemistry, if applicable. Omit byproducts such as water or bromide ion.

Concepts and reason

A compound is given with a reagent in the reaction and the product of the reaction with the correct stereochemistry needs to form. As hydroxide ion is given which is a strong nucleophile therefore, the reaction will follow the elimination mechanism.

Fundamentals

A haloalkane can reacts with a nucleophile to undergo elimination reaction and result in the formation of an alkene.

The general reaction is as follows:

Elimination reaction can be classified as ${\rm{E - }}1$ and ${\rm{E - 2}}$ . In ${\rm{E - }}1$ elimination reaction the reaction completes in two step 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, $3^\circ < 2^\circ < 1^\circ < {\rm{C}}{{\rm{H}}_3}$ .

Show the product of the reaction following the elimination mechanism by the abstraction of proton from the alpha-carbon by the nucleophile as shown below:

Show the product of the reaction following the elimination mechanism by the abstraction of proton from the other alpha-carbon by the nucleophile as shown below:

Compare the stability of both the products and write the major organic product as shown below:

Ans:

Hence, the major product of the reaction is as follows:

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