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Chapter 20: Problem 3

Predict the product(s) formed by addition of one mole of \(\mathrm{Br}_{2}\) to 2,4 -hexadiene.

Short Answer

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Question: Predict the product(s) formed by adding one mole of bromine (Br2) to 2,4-hexadiene. Answer: The product formed by the addition of one mole of bromine (Br2) to 2,4-hexadiene is 2,3-dibromo-4-hexene.

Step by step solution

01

Recognize the structure of 2,4-hexadiene

First, let's draw the structure of 2,4-hexadiene. 2,4-hexadiene is a molecule with six carbon atoms, with double bonds between C2-C3 and C4-C5. We can represent it as CH2=CH-CH=CH-CH2-CH3.
02

Identify the reactive sites of 2,4-hexadiene

Next, let's identify the reactive sites in 2,4-hexadiene where bromine will attack. The double bonds between C2-C3 and C4-C5 are nucleophilic, and they will react with electrophiles like bromine. The less substituted double bond will be more reactive, so the Br2 will attack primarily at C2-C3.
03

Electrophilic addition of bromine

When bromine approaches the C2-C3 double bond, the bromine atom closest to the double bond will form a bond with the C2 atom, and the double bond will break, forming a bromonium ion at C3. The structure of the bromonium ion will be: CH2-CH(Br)(+) -CH=CH-CH2-CH3
04

Ring opening reaction

Now, we have Br(-) as the nucleophile that will attack the carbocation. The Br(-) will attack the C3 atom, breaking the bromonium ion, forming the dibrominated product. The final product after the electrophilic addition of one mole of Br2 to 2,4-hexadiene will be: CH2-CHBr-CHBr-CH=CH-CH2-CH3 So, the product formed by the addition of one mole of \(\mathrm{Br}_{2}\) to 2,4-hexadiene is 2,3-dibromo-4-hexene.

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Most popular questions from this chapter

Propose a mechanism for the following Cope rearrangement.

Predict the major product formed by 1,4 -addition of \(\mathrm{HCl}\) to cyclopentadiene.

Write the frontier molecular orbital analysis for the cycloaddition of butadiene with butadiene when both interact in a suprafacial manner. Is this reaction allowed?

1,3-Butadiene is a gas at room temperature and requires a gas-handling apparatus to use in a Diels-Alder reaction. Butadiene sulfone is a convenient substitute for gasheated above its boiling point of \(110^{\circ} \mathrm{C}\), decomposes by a reverse Diels-Alder reaction to give s-cis-1,3-butadiene and sulfur dioxide. Draw Lewis structures for butadiene sulfone and \(\mathrm{SO}_{2}\); then, show by curved arrows the path of this reaction, which resembles a reverse Diels-Alder reaction.

Under certain conditions, 1,3-butadiene can function both as a diene and a dienophile. Draw a structural formula for the Diels-Alder adduct formed by reaction of 1,3-butadiene with itself.
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