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Q.What happens when primary, secondary and tertiary alcohols are – (क) Oxidised using acidified potassium permanganate solution. (1½) (ख) Passed over heated copper at 573 K. (1½)

Uttarakhand UbseUttarakhand Board Intermediate (Class 12) 2018Subjective· 3mImportance★★★★★
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Oxidation (KMnO4_4): 1^\circ$$\rightarrowacid, 2^\circ$$\rightarrowketone, 3^\circ$$\rightarrowresistant. Hot Cu/573 K: 1^\circ$$\rightarrowaldehyde, 2^\circ$$\rightarrowketone, 3^\circ$$\rightarrowalkene.

(k) Oxidation with acidified KMnO4_4.

  • Primary alcohol is oxidised first to an aldehyde and then further to a carboxylic acid: CH3CH2OH→KMnO4/H+CH3CHO→[O]CH3COOHCH_3CH_2OH \xrightarrow{KMnO_4/H^+} CH_3CHO \xrightarrow{[O]} CH_3COOH
  • Secondary alcohol is oxidised to a ketone (same number of carbons): (CH3)2CHOH→KMnO4/H+(CH3)2C=O(CH_3)_2CHOH \xrightarrow{KMnO_4/H^+} (CH_3)_2C{=}O
  • Tertiary alcohol has no H on the carbon bearing −-OH, so it resists oxidation under normal conditions (only breaks down under drastic conditions).

(kh) Passed over heated copper at 573 K.

  • Primary alcohol undergoes dehydrogenation to an aldehyde: CH3CH2OH→Cu, 573 KCH3CHO+H2CH_3CH_2OH \xrightarrow{Cu,\,573\,K} CH_3CHO + H_2
  • Secondary alcohol dehydrogenates to a ketone: …

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