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2-cyclopenten-1-one $\xrightarrow{\text{NaBH}_4/\text{EtOH}}$ ?
(1). (2-cyclopenten-1-ol (allylic alcohol))
(2). (Cyclopentanol (fully reduced))
(3). (Cyclopentanone (only C=C reduced))
(4). (Cyclopentanol with OH)
NaBH$_4$ does not reduce C=C double bond but reduces C=O to CHOH. Product: 2-cyclopenten-1-ol.
BETA
