Exam 11: Radical Reactions

Upon treatment of 1-methylcyclopentene with NBS and irradiation with UV light, exactly nine compounds (including stereoisomers) are formed. Draw all nine products.

Rank the following radicals in order of decreasing stability (most stable to least stable).

Use correct arrow formalism to show termination by coupling of two growing poly(vinyl chloride) chains.

Thermal cracking of butane can produce ethyl radicals via homolytic cleavage. Use correct arrow formalism to show this process.

When 1,1,4-trimethylcyclohexane is exposed to Br₂ and UV light, only one major product is obtained. How many distinct resonances in the (proton-decoupled) ¹³C NMR spectrum are observed in the product?

Use correct arrow formalism to show the propagation steps in the chlorination of propane to produce 2-chloropropane.

Cyclic compound A has molecular formula C₅H₁₀ and undergoes monochlorination to yield exactly three different constitutional isomers. Identify compound A and show the monochlorination products.

Propose an efficient synthesis of 4-penten-2-ol from propene.

When 2-methyl-1-propene is exposed to NBS and UV light, only one major product is obtained. How many distinct resonances in the (proton-decoupled) ¹³C NMR spectrum are observed in the product?

What reagents would best accomplish the following transformation?