Question

5. MTBE is the additive current the additive currently used in car gasoline to prevent knocking. A stud to prevent knocking. A student desig possible ways to prepare MTBE illustrated in the box below. -6 Na CH31 Synthetic Route A OCH3 CH30 Na Synthetic Route B MTBE CH3OH Synthetic Route C - What was the best method to prepare MTBE? Why? (2 Points)

Answer 1

ROUTE 1 IS THE BEST METHOD

Since this reaction is essentially a SN2 reaction hence attack of the nucleophile will be most facile when the substrate isleast hindered (Remember: In SN2 nucleophile always attack from the back side hence hinderance play a major role)

so In 2nd and 3rd choice we have an alkoxide ion as Nu- and alkyl halide as substrate which is highly hindere due to tert-butyl group hence no SN2 will take place (instead E2 elimination will take place)

Hence in 1st choice we have CH3I primary halide and t-BuO- as nucleophile so this will be best