Write the name of the product formed by the action of LiAlH4/ether on acetamide.
Solution and Explanation
The given compound is acetamide (CH3CONH2).
Lithium aluminium hydride (LiAlH4) is a powerful reducing agent that reduces amides to amines when used in anhydrous ether as solvent.
The reaction proceeds as: \[ CH_3CONH_2 \xrightarrow[\text{ether}]{\text{LiAlH}_4} CH_3CH_2NH_2 \]
Thus, acetamide is reduced to ethylamine.
- LiAlH4 reduces:
• Amides → Amines
• Aldehydes → Primary alcohols
• Ketones → Secondary alcohols
• Carboxylic acids and esters → Primary alcohols - The reaction removes the oxygen atom completely from the amide group.
Top Questions on Amines
- Give plausible explanation for each of the following:
Amides are less basic than amines. Amines are usually formed from amides, imides, halides, nitro compounds, etc. They exhibit hydrogen bonding which influences their physical properties. In alkyl amines, a combination of electron releasing, steric and H-bonding factors influence the stability of the substituted ammonium cations in protic polar solvents and thus affect the basic nature of amines. Alkyl amines are found to be stronger bases than ammonia. Amines being basic in nature, react with acids to form salts. Aryldiazonium salts, undergo replacement of the diazonium group with a variety of nucleophiles to produce aryl halides, cyanides, phenols and arenes.
How can you convert the following:
(i) Ethanoic acid to methanamine- Give the structures of A, B, and C in the following reaction sequences: (i)\; \(\mathrm{CH_3CH_2I} \xrightarrow[\ ]{\mathrm{NaCN}} A \xrightarrow[\ ]{\;\;HO^-\;/\;H_2O\;\;} B \xrightarrow[\;Br_2/NaOH\;]{} C\)
(ii)\; \(\mathrm{C_6H_5N_2^+Cl^-} \xrightarrow[\ ]{\mathrm{CuCN}} A \xrightarrow[\ ]{\;H_3O^+\;} B \xrightarrow[\ \Delta\ ]{\;NH_3\;} C\)
(iii)\; \(\mathrm{CH_3CH_2Br} \xrightarrow[\ ]{\mathrm{KCN}} A \xrightarrow[\ ]{\mathrm{LiAlH_4}} B \xrightarrow[\;273\,K\;]{\;HNO_2\;} C\) - How can you obtain the following?
(a) Aniline from ammonium benzoate
(b) Benzene diazonium chloride from nitrobenzene
(c) 2,4,6-Tribromoaniline from aniline - Arrange the following compounds in increasing order of their boiling point:
\[ \text{(CH}_3\text{)}_2\text{NH, CH}_3\text{CH}_2\text{NH}_2, \text{CH}_3\text{CH}_2\text{OH} \]
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