NEETChemistryHaloalkanes and Haloarenes
An unknown alkene 'X' undergoes the following sequence of reactions to yield 3-methylbutan-1-amine as the major final product: (i) HBr , benzoyl peroxide (ii) KCN (iii) Na(Hg) / C ₂ H ₅ OH The IUPAC name of the starting alkene 'X' is:
Options
- A2-Methylpropene
- BBut-1-ene
- CBut-2-ene
- D2-Methylbut-1-ene
Correct answer
A. 2-Methylpropene
Step-by-step solution
The problem can be solved by retrosynthetic analysis. The final product is 3-methylbutan-1-amine ( CH ₃- CH ( CH ₃)- CH ₂- CH ₂ NH ₂ ). This is formed by the reduction of a nitrile in step (iii). Therefore, the precursor nitrile must be 3-methylbutanenitrile ( CH ₃- CH ( CH ₃)- CH ₂- CN ). The nitrile is formed in step (ii) by the nucleophilic substitution of an alkyl bromide with KCN . Thus, the alkyl bromide must be 1-bromo-2-methylpropane ( CH ₃- CH ( CH ₃)- CH ₂ Br ). In step (i), 1-bromo-2-methylpropane is for