What is the Difference Between 1 2 Addition and 1 4 Addition?

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The main difference between 1,2-addition and 1,4-addition lies in the position of the carbon atoms in the conjugated diene that are involved in the addition reaction. In a 1,2-addition, the reactant adds to the first and second carbon atoms of the diene, resulting in a product where the added atoms or groups are adjacent to each other. In a 1,4-addition, the reactant adds to the first and fourth carbon atoms of the diene, resulting in a product where the added atoms or groups are separated by two carbon atoms.

Here are some key points about 1,2- and 1,4-additions:

  • The 1,2-addition has a smaller activation energy than the 1,4-addition, making it occur faster.
  • At low temperatures, the 1,2-addition product is favored, while at higher temperatures, the 1,4-addition product becomes more dominant.
  • The 1,4-addition product is more thermodynamically stable than the 1,2-addition product due to its more substituted double bond.

For example, when HBr is added to butadiene, the 1,2-addition product is formed when HBr bonds to the first carbon atom and the Br bonds to the second carbon atom, resulting in 1-bromo-2-butene. The 1,4-addition product is formed when HBr bonds to the first carbon atom and the Br bonds to the fourth carbon atom, resulting in 2-bromo-1-butene.

Comparative Table: 1 2 Addition vs 1 4 Addition

The difference between 1,2-addition and 1,4-addition lies in the position at which the new attacking molecule bonds to the double bond of a conjugated diene. Here is a summary of the two types of addition:

Addition Type Description Product Formation
1,2-Addition In this addition, the attacking molecule (e.g., HBr) bonds to the adjacent carbons of a double bond, resulting in the formation of a new C-H single bond and a C-Br single bond. This product is formed more rapidly than the 1,4-addition product at higher temperatures. The product is a mixture of 3,4-dibromo-1-butene and 1,4-dibromo-2-butene, with the 1,2-addition being the expected product.
1,4-Addition In this addition, the attacking molecule bonds to two carbon atoms separated in the carbon chain by two intervening atoms, forming a new C-H single bond on one end of the diene and a C-Br single bond on the other end. This product is more stable than the 1,2-addition product. The resultant product is primarily formed as the (E) isomer.

At low temperatures, the products are formed irreversibly and reflect the relative rates of the two competing reactions. As the temperature increases, the amount of 1,4 product increases.