Question

An alkane $C_8{H}_{18}$ is obtained as the only product subjecting a primary alkyl halide to the Wurtz reaction. On monobromination, this alkane yields a single isomer of a tertiary bromide. Write the structure of alkane and the tertiary bromide.

Answer 1

The wurtz reaction of an alkyl halide gives an alkane with double the number of carbon atoms present in the alkyl halide.

If wurtz reaction of a primary alkyl halide gives an alkane $C_8{H}_{18}$. Then, alkyl halide must contain four carbon atoms. The two possible primary alkyl halides having four carbon atoms are I & II.



Since, alkane $C_8{H}_{18}$ on monobromination yields a single isomer of tertiary alkyl halide, the alkane must contain tertiary hydrogen. This is possible only in this primary alkyl halide II, as it have tertiary hydrogen.

So, the reactions involved can be given as:.


So, the structure of alkane and tertiary bromide can be given as:.