Experiment 15

Title: Isomerism Objective: To identify two organic compounds X and Y Introduction: Isomers are molecules that have the same molecular formula, but have a different arrangement of the atoms in space. That excludes any different arrangements which are simply due to the molecule rotating as a whole, or rotating about particular bonds. In structural isomerism, that atoms are arranged in a completely different order. Reagents: Chemical X (aq) Chemical Y (aq) 2-4-dinitrophenyllhydrazine (aq) Silver nitrate Ammonia ( 1M) Iodine (potassium iodide) Sodium hydroxide (1M) Potassium manganate (VII) Apparatus: 8 test tubes and rack Beaker (250mL) Bunsen burner Corks Matches Procedure: Two organic compounds; liquid X and Y were provided. (These liquids are organic compounds and structural isomers). Tests (a) to (c) were carried out and observations and inferences were recorded.

Test (a) 1 ml of the compound (X and Y) was taken into 2 test tubes and about the same amount of distilled water was added and shaken.

Compound X Observation Soluble in water Cloudy solution was formed Pungent smell was produced i. ii.
Page 1 of 4

Inferences Unsaturated carbon ring is present. Heterogenous solution is formed.

Compound Y Observation Insoluble in water No change seen No smell was produced i. ii. iii. Inferences Saturated carbon ring is present. Homogenous solution is formed. Could be ether.

(i) Probable carbon chain lengths of the compounds. Compound A contains a carbon chain longer than 3C if its of aldehyde or ketone families. Compound B has a carbon chain length no longer than 3C. (ii) Possible functional group present in either compound X or Y. Compound B is either a carboxylic acid, alcohol or amino acid.

Test (b) 1 ml of 2, 4-dinitrophenylhydrazine reagent was taken into 2 test tubes and several drops of compound X and Y was added. Compound X Observation Yellowish-Orange precipitate was formed i. Inferences Presence of carbonyl group. (hydrazine formed).

Compound Y Observation No change in colour was seen. I. II. Inferences Compound Y does not react with 2, 4-dinitrophenylhydrazine. Compound Y is not a carbonyl compound.

Test (c) 5ml of compound X and Y was taken into 2 test tubes and 4ml of iodine in potassium iodide solution was added. Then sodium hydroxide solution was added drop by drop until the iodine colour was discharged. Compound X Observation Very insoluble Iodine colour started changing only after adding several drops ( about 10). A gas was evolved. Strong smell produced.
Page 2 of 4

Inferences i. The discharge of the blue-black iodine colour is a result of positive test for unsaturated carbon ring. ii. Iodine reacts with the compound X.

White precipitate was formed at the bottom, iodine colour layer on top. Compound Y Observation Inferences No change in colour i. Blue-black colour of iodine is not Tiny bubbles in solution. discharged due to presence of Gas evolved. saturated carbon ring. Strong smell produced. ii. Iodine does not react with the compound Y.

Test (d) 5mL of silver nitrate was poured into a test tube and a few drops of sodium hydroxide was added into it. (A grey-brown precipitate was formed). It was allowed to settle for several minutes before discarding as much of the supernatant liquid and the precipitate was retained. Ammonia was added drop by drop until the precipitate just dissolved. This solution was divided into 2 parts equally into two different test tubes. Two drops of Compound X and Y was added into each test tube respectively. Then both the test tubes were left in a beaker of hot water for few minutes. Compound X Observation Grey-brown solution was formed. Inferences Tollens reaction

RCHO + 2 {Ag(NH3)2}+ + 3 OH- RCOO- + 2Ag + NH3 + 2H2O Silver mirror Compound Y Observation Inferences A brownish solution was formed Shows the presence of ketone.

Test (e) 1mL of potassium manganate (VII) was taken into 2 test tubes and a few drops of Compound X and Y was added respectively into them and shaken. Compound X Observation Inferences i. Unsaturated carbon chain present. Grey-brown solution observed ii. Potassium manganate (VII) reacts with compound Y and brown MnO2 percipitate formed. Compound Y Observation Inferences i. Saturated carbon chain present. No change in colour observed
Page 3 of 4

Potassium manganate (VII) does not react with compound Y because compound Y has single bond which are all occupied. (iii) Structure of compound X

Systematic name for compound X

(iv)

Structure of compound Y

Systematic name for compound Y

Discussion : 1. Compound X is an organic compound which contains unsaturated carbon chain. This is why compound X is soluble in water, reacts with 2, 4-dinitrophenylhydrazine to form yellow-orange precipitate, decolourises blue-black potassium iodide, and changes purple colour potassium manganate (VII) solution into grey-brown. 2. Whereas compound Y is an organic compound which contains saturated carbon chain. Only single bonds are present in the chain and are occupied. Compound Y is insoluble in water, does not reacts with 2, 4-dinitrophenylhydrazine, is not soluble in potassium iodide, .. and no changes were seen when added into potassium manganate (VII) solution. Conclusion : Compound X and compound Y are organic compound which respectively have unsaturated and saturated carbon chain. Reference: Laboratory Manual (MF001 General Chemistry) http://en.wikipedia.org/wiki/Diethyl_ether Chemistry Ninth Edition, Raymond Chang

Page 4 of 4