Question

What would be the product when neopentyl chloride reacts with sodium ethoxide?

Options

• 2-Methyl-butan-2-ol

• Neo pentyl alcohol

• Both 2-Methyl-butan-2-ol and Neo pentyl alcohol

• 2-Methyl-but-2-ene

Answer 1

2-Methyl-but-2-ene

Explanation:

\[\begin{array}{cc}
\phantom{.....}\ce{CH3}\phantom{........................}\ce{CH3}\phantom{............................}\ce{CH3}\phantom{....................}\ce{CH3}\phantom{........}\\
\phantom{....}|\phantom{...........................}|\phantom{................................}|\phantom{........................}|\phantom{.........}\\
\ce{CH3-C-CH2-Cl ->[NaOC2H5][\underset{mechanism}{E1}] CH3-C-\overset{⊕}{C}H2->[{carbocation rearrangement}] CH3-\underset{⊕}{C}-CH2-CH3 -> CH3-C=CH-CH3}\\
\phantom{}|\phantom{...........................}|\phantom{..............................................................}\\
\phantom{.}\ce{CH3}\phantom{.......................}\ce{CH3}\phantom{............................................................}
\end{array}\]