chemistry 2412l aldehydes/ketones pre-lab lecture
DESCRIPTION
Procedure Notes The four tests are: 1.2,4-Dinitrophenylhydrazone formation 2.Semicarbazone formation 3.Oxidation 4.Iodoform test Some pictures of these test that may be helpful to you can be found at this link.at this linkTRANSCRIPT
Chemistry 2412LAldehydes/Ketones pre-lab lecture
Properties of Aldehydes and Ketones• In this experiment you will be investigating the chemical
properties of aldehydes and ketones.• Although aldehydes and ketones are very similar in
structure and reactivity, there are some tests that can distinguish between the two functional groups.
• You will observe results of 4 tests on known compounds, and use your observations to identify an unknown compound. You will also determine the IR spectrum of your known. The unknown will be an aldehyde or a ketone. If it is a ketone, you will need to determine if it is a methyl ketone.
Procedure Notes• The four tests are:
1. 2,4-Dinitrophenylhydrazone formation2. Semicarbazone formation3. Oxidation4. Iodoform test
• Some pictures of these test that may be helpful to you can be found at this link.
Procedure Notes• Aldehydes and ketones react with a number of
nitrogen-containing compounds through nucleophilic addition and subsequent loss of water to give products that have a carbon-nitrogen double bond.
• These reactions are useful in distinguishing aldehydes and ketones from other functional groups.
• If the precipitate formed is isolated and the melting point determined, specific aldehydes and ketones can be identified.
• Two reagents that frequently yield crystalline derivatives are 2,4-dinitrophenylhydrazine and semicarbazide. You will use these reagents in tests 1 and 2.
Procedure Notes1. 2,4-Dinitrophenylhydrazone formation:
– 2,4-Dinitrophenylhydrazine reacts with ketones and aldehydes, and is used to distinguish these functional groups from other carbonyl compounds, such as esters, which do not react.
– The formation of a red or orange precipitate (a 2,4-dinitrophenylhydrazone) constitutes a positive test.
NO2
NO2
NHH2NC O
R
R
+ NO2
NO2
NHNC
R
R
+ H2O
ketone or aldehyde 2,4-dinitrophenylhydrazine 2,4-dinitrophenylhydrazone
(a solid)
Procedure Notes2. Semicarbazone formation:
– Semicarbazide reagent reacts with ketones and aldehydes to form solid semicarbazones.
CNHH2NC O
R
R
+ CNHNC
R
R
+ H2O
ketone or aldehyde semicarbazide semicarbazone
(a solid)
O
NH2
O
NH2
Procedure Notes3. Oxidation using chromic acid:
– This test is based on the reduction of chromium(VI), which is orange, to chromium(III), which is green, when an organic compound is oxidized by the chromium reagent.
– A change in color of the reagent from orange to blue-green represents a positive test.
– Aldehydes are oxidized by the reagent to carboxylic acids; ketones are not oxidized at all by the reagent. As a result, this reaction can be used to distinguish aldehydes from ketones.
C
O
R H
H2CrO4
C
O
R OH
C
O
R R
H2CrO4No reaction
Procedure Notes4. Iodoform test:
– Methyl ketones (RCOCH3) can be distinguished from other ketones.
– Methyl ketones react rapidly with iodine under basic conditions to give a carboxylate (RCO2
-) and iodoform (CHI3).– Iodoform is a pale yellow solid, and its
appearance indicates a positive test.
R C CH3
O
+ 3 I2 + 4 NaOH R C O
O
Na + CHI3 + 3 NaI + 3 H2O
Safety Notes• Although only small amounts of reagents
are used in this experiment, some are strongly acidic or basic and appropriate care should be taken in handling them.
• If any of chemicals are spilled on the skin rinse thoroughly with water, then wash with soap and water.
• Waste from the iodoform test must go in the halogenated waste container. All other waste may go in the non-halogenated waste container.