NEETChemistryHydrocarbons
An alkyl bromide X with the molecular formula C₅H₁₁Br exhibits the highest rate of dehydrohalogenation among all its structural isomers. When treated with alcoholic KOH, X undergoes elimination to majorly form an alkene Y. Ozonolysis of Y followed by treatment with Zn/H₂O yields a mixture of propan-2-one and ethanal. The IUPAC name of the alkyl bromide X is:
Options
- A2-Bromo-3-methylbutane
- B1-Bromo-3-methylbutane
- C2-Bromopentane
- D2-Bromo-2-methylbutane
Correct answer
D. 2-Bromo-2-methylbutane
Step-by-step solution
The reductive ozonolysis of alkene Y yields propan-2-one ( CH₃COCH₃ ) and ethanal ( CH₃CHO ). Working backwards, the structure of alkene Y must be 2-methylbut-2-ene ( CH₃-C(CH₃)=CH-CH₃ ). The alkyl bromide X ( C₅H₁₁Br ) that yields 2-methylbut-2-ene as the major product upon dehydrohalogenation could be either 2-bromo-2-methylbutane (a 3^ halide) or 2-bromo-3-methylbutane (a 2^ halide). The problem states that X exhibits the highest rate of dehydrohalogenation among its structural isomers. Since tertiary alkyl hali