Question
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2-Hydroxycyclopentane carbaldehyde.
Benzyl alcohol to benzoic acid.
$\text{CH}_3-\text{CH}_2-\text{CH}_2-\text{O}-\text{CH}_3+\text{HBr}\xrightarrow{\ \ \ }$
$\text{C}_6\text{H}_5\text{N}_2\text{Cl}\xrightarrow[(\text{ii})\text{NaNO}_2/\text{Cu}.\Delta]{(\text{i})\text{HBF}_4}$
$\text{CH}_3\text{COCH}_2\text{COOC}_2\text{H}_5\xrightarrow[(\text{ii})\text{ H}^+]{(\text{i})\text{ NaBH}_4}$