Identify Z in the sequence of reactions:

Identify Z in the sequence of reactions:
  1. CH3-CH23-O-CH2CH3
  2. CH32CH2-O-CH2CH3
  3. CH3CH24-O-CH3
  4. CH3CH2-CHCH3-O-CH2CH3

Solution

\(\begin{array}{l} \qquad \qquad \qquad \qquad \qquad \qquad \qquad \qquad ~~~\quad \text{Br}\\ \mathrm{CH}_3 \mathrm{CH}_2 \mathrm{CH}=\mathrm{CH}_2 \xrightarrow[\mathrm{H}_2 \mathrm{O}_2]{\mathrm{HBr}} \mathrm{CH}_3 \mathrm{CH}_2 \underset{\Large | ~~}{\mathrm{CH}}- \stackrel{\Large | \quad}{\mathrm{CH}_2} \xrightarrow{\mathrm{C}_2 \mathrm{H}_5 \mathrm{ONa}} \mathrm{CH}_3-\left(\mathrm{CH}_2\right)_3-\mathrm{OCH}_2-\mathrm{OCH}_2 \mathrm{CH}_3 \\ \qquad \qquad \qquad \qquad \qquad \qquad \qquad \quad ~~ \text{H} \end{array}\)
HBr in presence of peroxide gives anti Markovnikoff addition product.
1o alkyl halide on reaction with C2H5ONa gives SN2 reaction.

Asked in: NEET 2014

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