# What product do you get when you react 3-bromocyclopentene with NaOCH_2CH_3 dissolved in HOCH_2CH_3?

$\text{Sodium cyclopentadienide?}$
${C}_{5} {H}_{7} B r + N a O E t \rightarrow {C}_{5} {H}_{6} + N a B r \downarrow + E t O H$
${C}_{5} {H}_{6} + N a O E t \rightarrow {\left[{C}_{5} {H}_{5}\right]}^{-} N {a}^{+} + E t O H$
$\text{1 equiv}$ gives the diene, ${C}_{5} {H}_{6}$; the 2nd equiv gives cyclopentadienyl anion. These days, in inorganic laboratories, you can prepare $100 \cdot g$ quantities of base-free $N a C p$ simply by boiling up sodium metal with dicyclopentadiene, ${C}_{10} {H}_{12}$,