Question

The following is not an appropriate reaction for the preparation of $t-butylethylether$.


$A$: What would be the major product of this reaction?

$B$: Write a suitable reaction for the preparation of $t-butylethylether$.

Answer 1

$A$:
Major product
The major product of the given reaction is
$2-methylprop-1-ene\text{and not}t-butylethylether$.
It is because sodium ethoxide can act as a nucleophile as well as a strong base and we have here $3^{\circ }$ alkyl halide due to which sodium ethoxide will act as a strong base in this case and hence, elimination reaction predominates over substitution.

$2-methylprop-1-ene$

$B$:

Preparation of $t-butylethylether$

If the reaction proceeds as shown above, major product in the case would be the elimination product i.e., $2-methylprop-1-ene$.
To obtain $t-butylethylether$ as a major product, ethyl chloride needs to be reacted with sodium $t-butylethoxide$, which will give nucleophilic substitution reaction instead of elimination.
$t-butylethylether$ can be prepared as: