Reaction with 2,4-dinitro phenylhydrazine 2,4-DNP reacts with both aldehydes and ketones. The product is an orange precipitate, It can be used as a test for a carbonyl group in a compound. Use 2,4-DNP to identify if the compound is a carbonyl. Then to differentiate an aldehyde from a ketone use Tollen’s reagent. NO2 O2N H3C C H2N NH H O + NO2 O2N 3CH C NH NH H OH NO2 O2N 3CH C N NH H addition elimination of water .. 2,4-DNP orange precipitate You don’t need to learn these equations for the exam Tollen’s Reagent CH3CHO + 2Ag+ + H2O CH3COOH + 2Ag + 2H+ Reagent: Tollen’s Reagent formed by mixing aqueous ammonia and silver nitrate. The active substance is the complex ion of [Ag(NH3 )2 ] + . Conditions: heat gently Reaction: aldehydes only are oxidised by Tollen’s reagent into a carboxylic acid and the silver(I) ions are reduced to silver atoms Observation: with aldehydes, a silver mirror forms coating the inside of the test tube. Ketones result in no change. The melting point of the crystal formed can be used to help identify which carbonyl was used. Take the melting point of orange crystals product from 2,4-DNP. Compare melting point with known values in database
/
~
~
~
/
6.1.2 Carbonyl compounds
Characteristic tests for carbonyl compounds (d) use of 2,4-dinitrophenylhydrazine to: (i) detect the presence of a carbonyl group in an organic compound (ii) identify a carbonyl compound from the melting point of the derivative The equation for this reaction is not required. Structure of derivative not required. PAG7 (see also 6.3.1 c) HSW4 Qualitative analysis. (e) use of Tollens’ reagent (ammoniacal silver nitrate) to: (i) detect the presence of an aldehyde group (ii) distinguish between aldehydes and ketones, explained in terms of the oxidation of aldehydes to carboxylic acids with reduction of silver ions to silver. In equations involving Tollens’ reagent, [O] is acceptable. PAG7 (see also 6.3.1 c) HSW4 Qualitative analysis.