
Which of the following reactions does not yield an amine:
A. $R - X + N{H_3} \to $
B. $R - CH = NOH + {[H]^{ + Na/{C_2}{H_5}}}$
C. $R - CN + {H_2}O$ ${H^ + }$
D. $R - CON{H_2}$ $LiAl{H_4}$
Answer
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Hint: A hydrolysis reaction is the one in which a water molecule $({H^ + })$ is added to split the compound in two parts. In this reaction a molecule of water breaks down the chemical bond.
Complete answer:
An amide group also known as carboxamide is a compound with molecular structure where there are organic groups or hydrogen atoms. The bond which is formed when an amide group is attached is known as peptide bond.
Similarly an oxime or an amidoxime is a chemical compound with a molecular structure ${R^1}C( = NOH)N{R^2}{R^3}$. The hydrolysis of amidoxime takes place in presence of inorganic acids in which the oximes gets decomposed in ketone or aldehyde group. In presence of the metal Sodium this amidoxime gets reduced into either primary, secondary or tertiary amines.
Amide formation can take place through multiple ways. The carboxylic acid when mixed with $N{H_3}$ at room temperature gives formation to the amide group. Acetamide $C{H_3} - CON{H_2}$ on treatment with $LiAl{H_4}$ get reduced into corresponding amine group which is ethylamine $C{H_3}C{H_2} - N{H_2}$ .
A cyanide group $R - CN$ on hydrolysis gives acids. It is an acid- base catalyzed reaction in which the carbonyl group becomes protonated and leads to nucleophile attacks on the carbonyl group of the amide and hydrolyses of compounds with carboxylic acid takes place.
$RCN + 2{H_2}O$ (${H^ + }$) $\longrightarrow $ $RCOOH + N{H_3}$
Therefore in all the options except the one which cyanide group yields amine group.
Complete answer:
An amide group also known as carboxamide is a compound with molecular structure where there are organic groups or hydrogen atoms. The bond which is formed when an amide group is attached is known as peptide bond.
Similarly an oxime or an amidoxime is a chemical compound with a molecular structure ${R^1}C( = NOH)N{R^2}{R^3}$. The hydrolysis of amidoxime takes place in presence of inorganic acids in which the oximes gets decomposed in ketone or aldehyde group. In presence of the metal Sodium this amidoxime gets reduced into either primary, secondary or tertiary amines.
Amide formation can take place through multiple ways. The carboxylic acid when mixed with $N{H_3}$ at room temperature gives formation to the amide group. Acetamide $C{H_3} - CON{H_2}$ on treatment with $LiAl{H_4}$ get reduced into corresponding amine group which is ethylamine $C{H_3}C{H_2} - N{H_2}$ .
A cyanide group $R - CN$ on hydrolysis gives acids. It is an acid- base catalyzed reaction in which the carbonyl group becomes protonated and leads to nucleophile attacks on the carbonyl group of the amide and hydrolyses of compounds with carboxylic acid takes place.
$RCN + 2{H_2}O$ (${H^ + }$) $\longrightarrow $ $RCOOH + N{H_3}$
Therefore in all the options except the one which cyanide group yields amine group.
Therefore, the correct option is (C) .
Note:An amide derivative can also get decomposed into amine by Beckmann rearrangement and a Hoffman degradation reaction in presence of f alkali hypochlorites.
Note:An amide derivative can also get decomposed into amine by Beckmann rearrangement and a Hoffman degradation reaction in presence of f alkali hypochlorites.
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