Which reaction is not possible for acetic anhydride?

Options

A. `(CH_(3)overset(O)overset(||)C)_(2)O+2HN(CH_(3))_(2)rarr CH_(3)overset(O)overset(||)(C)N(CH_(3))_(2)+CH_(3)CO_(3)^(-) +H_(2)overset(+)(N)(CH_(3))_(2)`
B. `(CH_(3)overset(O)overset(||)C)_(2)O +CH_(3)CH_(2)OH rarr CH_(3)overset(O)overset(||)(C)OCH_(2)CH_(3)+CH_(3)CO_(2)H`
C. `(CH_(3)overset(O)overset(||)C)_(2)O +C_(6)H_(6) overset(AICI_(3))rarr CH_(3)overset(O)overset(||)(C)CI +CH_(3)CO_(2)H`
D. `(CH_(3)overset(O)overset(||)C)_(2)O +NaCI rarr CH_(3)overset(O)overset(||)(C)CI +CH_(3)CO_(2)^(-)Na^(+)`

Answer

D

Explanation

Weak base cannot replace strong base.
`(CI^(Theta) lt CH_(3)COO^(Theta) lt C_(2)H_(5)O^(Theta) lt NH_(2)^(Theta) rArr` Basicity order)