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Question
How can the following conversions be brought about:
(i) Acetaldehyde to propan-2-ol.
(ii) Nitrobenzene to p-aminoazobenzene.
(iii) Acetic acid to methylamine.
(iv) Aniline to benzene.
(i) Acetaldehyde to propan-2-ol.
(ii) Nitrobenzene to p-aminoazobenzene.
(iii) Acetic acid to methylamine.
(iv) Aniline to benzene.
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Solution
(i) Acetaldehyde to propan-2-ol.
Acetaldehyde reacts with methyl magnesium iodided followed by acid hydrolysis to form propan-2-ol.
CH3CHO(i)CH3MgI−−−−−−−→(ii)H3O+CH3CH|OH CH3
(ii) Nitrobenzene to p-aminoazobenzene.A mixture of nitrobenzene and p-amino nitrobenzene is reduced in alkaline medium to obtain p-aminoazobenzene.
C6H5NO22[H]−−−−−−−−−−−−−→alkaline reducing agentC6H5NO
p−NH2−C6H4NO24[H]−−−−−−−−−−−−−→alkaline reducing agentp−NH2−C6H4NHOH
p−NH2−C6H4NHOH+C6H5NO−H2O−−−−→p−NH2−C6H4N=N(→O)−C6H5
p−NH2−C6H4N=N(→O)−C6H52[H]−−−−−−−−−−−−−→alkaline reducing agentp−NH2−C6H4N=N−C6H5
(iii) Acetic acid to methylamine.The reaction of acetic acid with ammonia followed by heating gives acetamide. This is followed by Hofmann bromamide reaction to obtain methylamine.
CH3−COOH(i)NH3−−−−−−−→(ii)Δ−H2OCH3−CONH2Br2/KOH−−−−−−−−−−−−−−−−−→Hofmann bromamide reactionCH3NH2
(iv) Aniline to benzene.The diazotization of aniline with nitrous acid at low temperature gives benzene diazonium chloride. The diazo group is then replaced with H atom by treatment with hypophosphorus acid to obtain benzene.
C6H5−NH2HCl/NaNO2−−−−−−−−→0−5oCC6H5N2ClH3PO2−−−−−−−−−−−−→hypophosphorus acidC6H6+N2+HCl
Acetaldehyde reacts with methyl magnesium iodided followed by acid hydrolysis to form propan-2-ol.
CH3CHO(i)CH3MgI−−−−−−−→(ii)H3O+CH3CH|OH CH3
(ii) Nitrobenzene to p-aminoazobenzene.
A mixture of nitrobenzene and p-amino nitrobenzene is reduced in alkaline medium to obtain p-aminoazobenzene.
C6H5NO22[H]−−−−−−−−−−−−−→alkaline reducing agentC6H5NOp−NH2−C6H4NO24[H]−−−−−−−−−−−−−→alkaline reducing agentp−NH2−C6H4NHOH
p−NH2−C6H4NHOH+C6H5NO−H2O−−−−→p−NH2−C6H4N=N(→O)−C6H5
p−NH2−C6H4N=N(→O)−C6H52[H]−−−−−−−−−−−−−→alkaline reducing agentp−NH2−C6H4N=N−C6H5
(iii) Acetic acid to methylamine.
The reaction of acetic acid with ammonia followed by heating gives acetamide. This is followed by Hofmann bromamide reaction to obtain methylamine.CH3−COOH(i)NH3−−−−−−−→(ii)Δ−H2OCH3−CONH2Br2/KOH−−−−−−−−−−−−−−−−−→Hofmann bromamide reactionCH3NH2
(iv) Aniline to benzene.
The diazotization of aniline with nitrous acid at low temperature gives benzene diazonium chloride. The diazo group is then replaced with H atom by treatment with hypophosphorus acid to obtain benzene.
C6H5−NH2HCl/NaNO2−−−−−−−−→0−5oCC6H5N2ClH3PO2−−−−−−−−−−−−→hypophosphorus acidC6H6+N2+HClSuggest Corrections
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