alleryStart learning →**Williamson's synthesis** of $(\text{CH}_3)_3\text{C-O-CH}_3$ would best use:
- $(\text{CH}_3)_3\text{C-Cl}$ + $\text{CH}_3\text{ONa}$
- $(\text{CH}_3)_3\text{C-ONa}$ + $\text{CH}_3\text{Cl}$
- Two molecules of $(\text{CH}_3)_3\text{C-OH}$
- Both A and B equally
Show answer and solution
Correct answer: B. $(\text{CH}_3)_3\text{C-ONa}$ + $\text{CH}_3\text{Cl}$
S$_N$2 needs less-hindered substrate.
tert-butyl chloride would undergo elimination, not substitution (3° halide + strong base → alkene).
Use bulkier alkoxide (t-BuO⁻) + smaller alkyl halide (CH₃Cl).
**Williamson rule:** alkoxide from the bulkier side + alkyl halide from the smaller side.