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Question
Explain the following with suitable example:
(a) Clemmensen reduction
(b) Stephen reaction
(a) Clemmensen reduction
(b) Stephen reaction
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Solution
(a) Clemmensen reduction:
Carbonyl compounds (aldehydes and ketones), that are not sensitive to acids, are heated with zinc amalgam and conc HCl to give alkanes. Carbonyl group is reduced to methylene group. This reaction is often used to convert acyl benzenes to alkyl benzenes.
CH3CO−CH3+4[H]Zn-Hg / conc. HCl−−−−−−−−−−−→ΔCH3−CH2−CH3+H2O
(b) Stephen reaction:
Nitriles react with stannous chloride / HCl to form imine hydrochlorides. This is reduction reaction. The imine hydrochlirdes on acid hydrolysis gives aldehydes.
CH3−C≡N+2[H]SnCl2/dilHCl−−−−−−−−→CH3−CH=NHHClH3O+−−−→CH3−CHO+NH4Cl
Carbonyl compounds (aldehydes and ketones), that are not sensitive to acids, are heated with zinc amalgam and conc HCl to give alkanes. Carbonyl group is reduced to methylene group. This reaction is often used to convert acyl benzenes to alkyl benzenes.
CH3CO−CH3+4[H]Zn-Hg / conc. HCl−−−−−−−−−−−→ΔCH3−CH2−CH3+H2O
(b) Stephen reaction:
Nitriles react with stannous chloride / HCl to form imine hydrochlorides. This is reduction reaction. The imine hydrochlirdes on acid hydrolysis gives aldehydes.
CH3−C≡N+2[H]SnCl2/dilHCl−−−−−−−−→CH3−CH=NHHClH3O+−−−→CH3−CHO+NH4Cl
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