Question

Predict the products of the following reaction:

$A$: $C{H}_3-C{H}_2-C{H}_2-O-C{H}_3+HBr\to$

$B$:

$C$:

$D$: $(H_{3}C{)}_{3}C-O{C}_2{H}_5\stackrel{HI}{\to }$

Answer 1

$A$:
Products Obtained

When $1-Methoxypropane\text{reacts with}HBr$, it forms propanol and bromomethane.
The reaction is given as –

The reaction is called as Cleavage of ether in
presence of hydrogen halide, which involves protonation of ether and then removal of leaving group by halide ion in $S{N}_2$ manner


$B$:

Products Obtained
When ethoxy benzene reacts with $HBr$, it forms Phenol and bromoethane.

The reaction is given as –


The reaction is called as Cleavage of ether in
presence of hydrogen halide, which involves protonation of ether and then removal of leaving group by halide ion in $S{N}_2$ manner.

$C$:

Products Obtained
When nitrating mixture reacts with ethoxy benzene, introduction of nitro group occurs at ortho and para position. As ethoxy group increases electron density on ortho and para position during resonance, it is called as ortho-para directing group. Para product will be the major product as it is more favoured due to steric reasons.

The reaction is given as -



$D$:

Products Obtained
As $HI$ is a strong acid, it will protonate the oxygen on ether, to form a good leaving group $\left(C_2{H}_{5}OH\right)$.
When, one of the alkyl group of ether is tertiary, it follows $S{N}_1$ mechanism and involves formation of tertiary carbocation, when leaving group leaves. After that I- will attack on carbocation centre to give $tert-butyliodide$.

The reaction is given as -