Chapter 8, Problem 67P

Triethylamine, ${\left(C_2{H}_5\right)}_{3}N$, like all amines, has a nitrogen atom with an unshared pair of electrons, Dichlorocarbene also has an unshared pair of electrons, Both can be represented as shown below. Draw die structures of compounds D, E, and F.

${\left(C_2{H}_5\right)}_{3}N:+CC{I}_2\to D\left(anunstableadduct\right)$

$D\to E+C_2{H}_4\left(byan\text{intramolecular}\text{E2}\text{reaction}\right)$

$E\stackrel{H_{2}O}{\to }F\left(\begin{array}{l}Watereffectsareplacementthatisthereverseofthatusedtomakegem\\ -dichlorides\end{array}\right)$