Problems and exercisesSteric Effects
1. Order by SN2 rate
Order from fastest to slowest towards iodide: neopentyl bromide, bromoethane, 2-bromopropane, bromomethane and 2-bromo-2-methylpropane.
2. Linear chains
Why does 1-bromopropane (0.80) react at almost the same rate as bromoethane (1)?
3. Neopentyl bromide
Neopentyl bromide, (CH3)3CCH2Br, is a primary halide. Why does it react so slowly by SN2?
4. Synthesis of MTBE
To prepare methyl tert-butyl ether, (CH3)3COCH3, by an SN2 reaction, which combination would you choose: CH3Br + (CH3)3CO− or (CH3)3CBr + CH3O−?