Which reaction is not possible for acetic anhydride ?

Options

A. `(CH_(3)overset(O)overset(||)C)_(2)O+2HN(CH_(3))_(2) to CH_(3)overset(O)overset(||)CN(CH_(3))_(2)+CH_(3)CO_(2)^(-)+H_(2)overset(+)N(CH_(3))_(2)`
B. `(CH_(3)overset(O)overset(||)C)_(2)O+ CH_(3)CH_(2)OH to CH_(3)overset(O)overset(||)COCH_(2)CH_(3)+CH_(3)CO_(2)H`
C. `(CH_(3)overset(O)overset(||)C)_(2)O+C_(6)H_(6) overset(AlCl_(3))to CH_(3)overset(O)overset(||)C C_(6)H_(5)+CH_(3)CO_(2)H`
D. `(CH_(3)overset(O)overset(||)C)_(2)O+NaCl to CH_(3)overset(O)overset(||)C Cl+CH_(3)CO_(2)^(-)Na^(+)`

Answer

D

Explanation

Weak base cannot replace strong base.
`(Cl^(ϴ) lt CH_(3)COO^(ϴ) lt C_(2)H_(5)O^(ϴ) lt NH_(2)^(ϴ)implies "Basicity order")`