Free-Radical Bromination: Major Organic Products

What is the major organic product formed by free-radical bromination of the following compounds?

a) Methylcyclopentane

b) 2,2,3-Trimethylpentane

c) 1-Isopropyl-1-methylcyclopentane

Answer:

a) The major organic product formed by free-radical bromination of Methylcyclopentane is Bromomethylcyclopentane.

b) For 2,2,3-Trimethylpentane, the major product is 2-Bromo-2,2,3-trimethylpentane.

c) When 1-Isopropyl-1-methylcyclopentane undergoes free-radical bromination, the major product obtained is 1-Bromo-1-isopropyl-1-methylcyclopentane.

In the context of organic chemistry, free-radical bromination involves the reaction of a bromine atom with a hydrocarbon. The hydrocarbon will substitute a hydrogen atom with a bromine atom. This reaction is highly selective and usually occurs at the position of the most stable free radical.

For Methylcyclopentane, the major product of free-radical bromination occurs on the tertiary carbon, giving us Bromomethylcyclopentane. In the case of 2,2,3-Trimethylpentane, the bromination occurs at one of the tertiary carbons creating 2-Bromo-2,2,3-trimethylpentane as the major product. Lastly, for 1-Isopropyl-1-methylcyclopentane, bromination happens at the tertiary carbon in the isopropyl group giving 1-Bromo-1-isopropyl-1-methylcyclopentane as the major product.

Understanding the mechanism behind free-radical bromination and the resulting major organic products is crucial in organic chemistry as it helps predict and analyze chemical reactions.