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The photo-catalysed bromination of 2-methylbutane is a free radical substitution reaction. Under UV light, bromine molecules ($$Br_2$$) undergo homolytic cleavage to form bromine radicals ($$Br^\bullet$$). These radicals abstract hydrogen atoms from the alkane, leading to alkyl radicals. The stability of the alkyl radical determines the major product, as bromination is selective for the most stable radical.
The structure of 2-methylbutane is $$CH_3-CH(CH_3)-CH_2-CH_3$$. We identify the types of hydrogen atoms:
The stability order of alkyl radicals is tertiary > secondary > primary. Bromine radicals preferentially abstract the tertiary hydrogen due to its higher stability, even though there is only one tertiary hydrogen compared to multiple primary and secondary hydrogens.
Abstraction of the tertiary hydrogen at carbon 2:
$$ CH_3-\underset{\underset{CH_3}{|}}{CH}-CH_2-CH_3 + Br^\bullet \rightarrow CH_3-\underset{\underset{CH_3}{|}}{\overset{\bullet}{C}}-CH_2-CH_3 + HBr $$This forms a tertiary alkyl radical at carbon 2. This radical then reacts with a bromine molecule:
$$ CH_3-\underset{\underset{CH_3}{|}}{\overset{\bullet}{C}}-CH_2-CH_3 + Br_2 \rightarrow CH_3-\underset{\underset{CH_3}{|}}{C}-CH_2-CH_3 + Br^\bullet $$ $$ Br $$The product is 2-bromo-2-methylbutane ($$CH_3-CBr(CH_3)-CH_2-CH_3$$).
Comparing with the options:
Due to the high selectivity of bromine for tertiary hydrogens (relative rate approximately 1600 times that of primary), the major product is the tertiary bromide, 2-bromo-2-methylbutane.
Hence, the correct answer is Option D.
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