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Question of 87

Q.Predict the products:

(a) cyclohexanone + NH2OH ->
(b) C6H5-N2Cl (benzenediazonium chloride) + H3PO2 + H2O ->
(c) CH3-CO-C2H5 (butan-2-one) --Zn-Hg/HCl-->
Jharkhand JacJAC Intermediate Board 2024Subjective· 3mImportance★★★★★
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(a) a ketone plus hydroxylamine gives an oxime; (b) a diazonium salt with H3PO2/H2O undergoes reductive deamination (replaces -N2+ with -H); (c) Zn-Hg/HCl (Clemmensen conditions) reduces a ketone's C=O all the way to CH2.

(a) Cyclohexanone (a cyclic ketone, C=O in a six-membered ring) reacting with NH2OH (hydroxylamine): this is a standard nucleophilic addition-elimination at the carbonyl, forming the corresponding oxime and water.

Product: cyclohexanone oxime (the ring C=O becomes C=N-OH) + H2O.

(b) C6H5-N2+Cl- (benzenediazonium chloride) reacting with H3PO2 (hypophosphorous acid) and H2O: H3PO2 is a mild reducing agent that replaces the diazonium group (-N2+) with a hydrogen atom, releasing nitrogen gas - this is reductive deamination, used to remove an -NH2 group from an aromatic ring (via its diazonium salt) without substituting anything else in its place. …

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