An alkane C8H18 is obtained as the only product on subjecting a primary alkyle halide to Wurtz reaction.On monobromination this alkane yields a single isomer of a tertiary bromide .What is the structure of alkane and tertiary bromide?

1 Answer
Mar 1, 2018

2,5-dimethyl-hexane and 2-bromo-5-methyl-hexane

Explanation:

An alkane obtained from Wurtz reaction from a primary alkyl halide must be simmetrical, obtained from 2 molecules of 1-halogen-2-methyl-propane:

2 #(H_3C)_2CHCH_2X# + 2 #Na# #-># #(H_3C)_2CHCH_2CH_2CH_"(CH_3)_2 #

The monobromination of this alkane gives
2-bromo-5-methyl-hexane:

2 #(H_3C)_2CHCH_2CH_2CH_2(CH_3)_2 # +#Br_2# #->#
2 #(H_3C)_2CBrCH_2CH_2CH(CH_3)_2 #

The bromination involves C2 because the intermediate radical is a more stable tertiary radical