Question

Consider the general problem of converting a tertiary alkyl halide to an alkene, for example the conversion of tert-butyl chloride to 2-methlypropene. what experimental conditions would you choose to ensure that elimination is favored over substitution? show work please!

Answer 1

generally for synthesizing alkene E2 is better

but tert-butyl chloride cannot undergo E2 because it can form more stable carbo cation

once it forms more stable carbo cation then two reactions are competition

1. elimination

2. is substitution

here if you want to turn your carbo cation to wards E1 reaction

you need to increase the temperature

because we know that at lower temperature SN1 is favored whareas at elivated temperature E1 is favored

so raise the reaction temperature.