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Question:

Of the following, the oxime of which compound shows geometrical isomerism?

Formaldehyde

Acetone

Diethyl ketone

Benzaldehyde

Solution:

For benzaldehyde, C6H5CHO + NH2OH → C6H5CN(H)(OH)(anti) + C6H5CN(H)(OH)(syn) gives syn and anti benzaldehyde oximes. For other cases, only one product is formed. For acetone, (CH3)2CO + H2NOH → (CH3)2CNOH + H2O. For formaldehyde, HCHO + NH2OH → H2CNOH. For diethyl ketone, CH3CH2COCH2CH3 + NH2OH → CH3CH2CN(OH)CH3