An organic compound answers Tollen’s test. What is the functional group in the compound?
Answer
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Hint: Tollens test is used for compounds containing aldehydes and ketones as a functional group, aldehydes responds positively to this test while ketone does not. If a compound responds positively to Tollens test then the functional group of the compound will be aldehyde
Complete step by step answer:
Tollens’ test, which is also called a silver-mirror test, is a laboratory test used to differentiate between an aldehyde and a ketone and is named after German chemist Bernhard Tollen. The aldehyde oxides readily whereas ketone doesn’t. Tollens’ reagent is a colourless basic aqueous solution having silver ions attached to ammonia in it \[{\left[ {Ag{{\left( {N{H_3}} \right)}_2}} \right]^ + }\]. Tollens Reagent has a comparatively short shelf-life that is why this reagent is prepared directly in the laboratory and is not available commercially abundantly. It is prepared using a two-step procedure.
Step 1: Few drops of dilute \[NaOH\] is introduced into an aqueous solution of silver nitrate. This solution contains silver aquo complexes whereas water acts as a ligand. The hydroxide ions from water converts these aquo complexes into silver oxides which precipitates as a brown solid.
\[2AgN{O_3} + 2NaOH \to A{g_2}O\left( {{\text{brown ppt}}} \right) + 2NaN{O_3} + {H_2}O\]
Step 2: The brown precipitate of silver oxide generated above is now mixed with aqueous ammonia. This leads to the formation of \[{\left[ {Ag{{\left( {N{H_3}} \right)}_2}} \right]^ + }\] complex which is primary component of Tollens Reagent.
\[A{g_2}O\left( {{\text{brown ppt}}} \right) + 4N{H_3} + 2NaN{O_3} + {H_2}O \to 2\left[ {Ag{{\left( {N{H_3}} \right)}_2}} \right]N{O_3} + 2NaOH\]
This reagent oxidizes an aldehyde into the carboxylic acid. The reaction is accompanied by the reduction of metallic metallic silver, which turns the glass tube into a mirror.
Note:
Tollens Reagent refers to the chemical reagent which can also be used in the detection of an aromatic aldehyde functional group, or an alpha hydroxy ketone functional group.
Complete step by step answer:
Tollens’ test, which is also called a silver-mirror test, is a laboratory test used to differentiate between an aldehyde and a ketone and is named after German chemist Bernhard Tollen. The aldehyde oxides readily whereas ketone doesn’t. Tollens’ reagent is a colourless basic aqueous solution having silver ions attached to ammonia in it \[{\left[ {Ag{{\left( {N{H_3}} \right)}_2}} \right]^ + }\]. Tollens Reagent has a comparatively short shelf-life that is why this reagent is prepared directly in the laboratory and is not available commercially abundantly. It is prepared using a two-step procedure.
Step 1: Few drops of dilute \[NaOH\] is introduced into an aqueous solution of silver nitrate. This solution contains silver aquo complexes whereas water acts as a ligand. The hydroxide ions from water converts these aquo complexes into silver oxides which precipitates as a brown solid.
\[2AgN{O_3} + 2NaOH \to A{g_2}O\left( {{\text{brown ppt}}} \right) + 2NaN{O_3} + {H_2}O\]
Step 2: The brown precipitate of silver oxide generated above is now mixed with aqueous ammonia. This leads to the formation of \[{\left[ {Ag{{\left( {N{H_3}} \right)}_2}} \right]^ + }\] complex which is primary component of Tollens Reagent.
\[A{g_2}O\left( {{\text{brown ppt}}} \right) + 4N{H_3} + 2NaN{O_3} + {H_2}O \to 2\left[ {Ag{{\left( {N{H_3}} \right)}_2}} \right]N{O_3} + 2NaOH\]
This reagent oxidizes an aldehyde into the carboxylic acid. The reaction is accompanied by the reduction of metallic metallic silver, which turns the glass tube into a mirror.
Note:
Tollens Reagent refers to the chemical reagent which can also be used in the detection of an aromatic aldehyde functional group, or an alpha hydroxy ketone functional group.
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