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Question
Acetaldehyde, Acetone, Di-tert-butyl ketone, Methyl tert-butyl ketone (reactivity towards HCN)
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Solution
When HCN reacts with a compound, the attacking species is a CN− nucleophile. Therefore, as the negative charge on the compound increases, its reactivity with HCN decreases. In the given compounds, the +I effect increases as shown below. It can be observed that steric hindrance also increases.
Hence, the given compounds can be arranged according to their increasing reactivities toward HCN as:
Di-tert-butyl ketone < Methyl tert-butyl ketone < Acetone < Acetaldehyde
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