Addition Reaction of 1,3-Diene with HBr

Very Hard Organic Chemistry Addition Reactions

Consider a 1,3-diene compound, 2,4-hexadiene, which undergoes a reaction with hydrogen bromide (HBr) at low temperatures. The reaction involves the addition of HBr across the double bonds. Which of the following statements accurately describes the product formed from this addition reaction?

Remember that in addition reactions involving conjugated systems, Markovnikov's rule may apply, and carbocation stability plays a significant role in determining the major product. Additionally, consider the mechanism by which HBr adds to the diene and the regioselectivity of the product.

The product is a single dibrominatedalkane, with bromine added to the first and last carbon of the chain.

The product is a mixture of two regioisomers: one with bromine on the first carbon and hydrogen on the third carbon, and the other with bromine on the second carbon and hydrogen on the fourth carbon.

The product is a dibrominated alkane where bromine adds to both ends of the diene, favoring the formation of a more stable double bond.

The reaction yields a single product, 2-bromo-3-hexene, resulting from anti-Markovnikov addition of HBr.

Hint

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