Identification of an Unknown Organic Compound

Mark Riley
Task Practical report

Introduction

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon with exception of a few types of compounds such as carbonates, carbides and cyanides. One or more of the carbon atoms are often covalently linked to atoms of other elements, most commonly hydrogen, oxygen, or nitrogen. Organic compounds are found in nature but can also be synthesized in the laboratory. We encounter so many organic compounds everyday, such as when we use perfumes or even drink a glass of alcohol. Each organic compound belongs to a particular chemical family and this experiment will investigate aldehydes, ketones, alkyl halides, carboxylic acids and alcohols- culminating in an evaluation of to which family an unknown organic sample belongs to.

Aim

To identify an unknown organic compound using a pre-prepared flow chart.

Hypothesis

By following the prepared flow chart, the unknown organic sample will be correctly identified. (Provided that steps & procedures are followed as carefully and accurately as possible)

Method

1. Follow the procedures in the series of tests outlined on the flow chart. 2. Using the results, determine the nature of the unknown organic compound. 3. Knowing the nature of the unknown compound, determine (even if by elimination) the family to which the unknown sample belongs. 4. Use confirmation tests to confirm these results. 5. If there is more than one organic compound listed that belongs to this same family, conduct further experimentation using boiling points or density to identify the compound.

(refer to flow chart and pages 5-9)

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Equipment                     Safety glasses Lab coat Rubber gloves Test tubes Blue litmus paper Dropping pipettes Bulb pipette 250mL beaker Digital scales Test tube rack Bunsen burner Heating mantle or oil bath Reflux apparatus Thermometer Heat resistant mat Tripod Gauze Retort stand Clamp Chemicalso o o o o o o o o o o 1M H2SO4 (Sulphuric acid) 0.1M K2Cr2O7 (Potassium dichromate) 0.1M AgNO3 (Silver nitrate) 2M NH3 (Ammonia) NaHCO3 (Sodium bicarbonate) 2-butanol Sodium metal 2-methyl-2-propanol Ethanol KOH (potassium hydroxide) 2M HNO3 (Nitric acid)

Safety Precautions          Some of the chemicals being used are considered to be toxic and gloves as well as safety glasses should be worn throughout the experiment. Check that the eye wash basin is functioning correctly before starting the experiment. A pathway to the wash and eye wash basin should be clear at all times. A chemical & flame retardant protective lab coat should be worn during the experiment. Fully covered shoes must be worn. Work benches should be kept clear and used equipment should be rinsed after use. All chemicals being used should be clearly labeled. Chemicals are flammable so open containers must be kept away from flames. Much care should be taken when using sodium as it is very reactive.

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Organic Compound Chemical Family Chemical Formula

1-propanol Alcohol Primary C3 H8 O

1-butanol Alcohol Primary C4 H10 O

2-butanol Alcohol Secondary C4 H10 O

2-methyl-2propanol Alcohol Tertiary C4 H10 O

dichloromethane Alkyl Halide Cl2 H2 C

Structure

CONFIRMATION TESTS Use density wherever possible Boiling point Density 97.4°C (96-98) 𝟏𝟔. 𝟎𝟕 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

118°C (116-120) 𝟏𝟔. 𝟐𝟎 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

99.5°C (99-101) 16.14 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

82.3°C (81-83) 𝟏𝟓. 𝟕𝟕 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

61.7°C (96-98) 𝟐𝟔. 𝟒𝟎 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

Organic Compound Chemical Family Chemical Formula

methanal Aldehyde CH3 O

propanone Ketone C3 H6 O

propanoic Acid Carboxylic Acid C3 H6 O2

ethanoic Acid Carboxylic Acid C2 H4 O2

Structure

CONFIRMATION TESTS Use density wherever possible Boiling point Density 100°C 𝟐𝟏. 𝟓𝟔 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

56.1°C (55-58) 𝟏𝟓. 𝟕𝟎 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

141°C (139-142) 𝟏𝟗. 𝟖𝟔 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

117.9°C (116-119) 𝟐𝟎. 𝟗𝟖 𝐺𝑟𝑎𝑚𝑠
20𝑚𝐿

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THIS BLANK PAGE IS WHERE THE FLOWCHART GOES

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TEST 1.

Test Number 1 Equipment Procedure
(also see flow chart)

•Test tube

•Test tube rack

•Distilled water

•Dropper

•Blue litmus paper

1. Add a few drops of distilled water into a test tube along with 10 drops of the unknown organic sample. 2. Test the mixture using blue litmus paper. The unknown sample and the water were miscible. The solution remained colourless and transparent. The litmus paper did not undergo any colour change. Blue litmus paper will turn red if [H+] present which identifies a solution as acidic. From the organic compounds listed, only carboxylic acid will ionize to any extent (H-atom attached to the –OH group).

Observations

Discussion The litmus paper did not undergo any colour change and remained blue indicating the unknown solution was not acidic, thus eliminating carboxylic acid as a possible family to which the unknown sample could belong to. Families & compounds eliminated The carboxylic acid family of organic compounds have been eliminated which include propanoic acid and ethanoic acid. Alkyl halides Primary alcohols Secondary alcohols Tertiary alcohols Aldehydes Ketones Dichloromethane 1-propanol, 1-butanol 2-butanol 2-methyl-2-propanol Methanal Propanone

Remaining possibilities

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TEST 2.

Test Number 2 Equipment •Test tube •Test tube rack •1M H2SO4 sulphuric acid •0.1M K2Cr2O7 potassium dichromate •Dropper

Procedure

1. Place 10 drops of the unknown substance into a test tube. 2. Add 20 drops of 1M H2SO4 sulphuric acid into the test tube. 3. Add 5 drops of K2Cr2O7 potassium dichromate

Observations

The solution was miscible and orange. The solution remained orange and no noticeable reaction occurred.

K2Cr2O7 potassium dichromate is easily reduced & works as a mild oxidant. K2Cr2O7 is orange & when reduced (𝐶𝑟 6+ → 𝐶𝑟 3+) it turns green. When a reactant is reduced another reactant has been oxidized. The only organic compounds listed that can be oxidised are as followsPrimary Alcohol OXID→ Aldehyde Aldehyde OXID→ Carboxylic acid Secondary Alcohol OXID→ Ketone

Discussion

A positive test (orange to green) therefore indicates that one of the substances underlined above is present. A carboxylic acid can be oxidized to CO2 + H2O but this is with much difficulty and for the purpose of this experiment will be ignored. In this test the solution remained orange, so there must not have been any primary alcohols, secondary alcohols or aldehydes present. Therefore all three ofthese can be eliminated as possibly being the unknown organic sample.

Families & compounds eliminated Remaining possibilities

Primary alcohols have been eliminated which include 1-propanol and 1-butanol. 2-butanol is no longer a possibility either as all secondary alcohols have been eliminated. Methanol is from the aldehyde family which has also been eliminated. Alkyl halides Tertiary alcohols Ketones Dichloromethane 2-methyl-2-propanol Propanone

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TEST 4.

Test Number 3 Equipment Procedure •Test tube •Test tube rack •Sodium metal •Dropper

1. Add 5 drops of the unknown organic sample to a clean DRY test tube. 2. Carefully add a small piece of sodium metal to the test tube. There was no visible reaction. The sodium metal stayed in a solid state and underwent no transformation. The unknown sample remained colourless and transparent.

Observations

Discussion

Just as sodium reacts with water to liberate hydrogen gas so too does sodium liberate hydrogen from alcohols or carboxylic acids. A positive test (fizzing as the hydrogen gas is released) indicates that the substance is either a carboxylic acid or an alcohol. Because no reaction happened when the sodium metal was added to the unknown organic sample, it can now be deduced that the organic sample is not a tertiary alcohol. This test has also further proved the results from the previous tests that had already eliminated primary alcohols, secondary alcohols and carboxylic acids as being the unknown organic sample.

Families & compounds eliminated Remaining possibilities

2-methyl-2-propanol is a tertiary alcohol and the possibility that the unknown organic sample may be a tertiary alcohol has now also been eliminated. Alkyl halides Ketones Dichloromethane Propanone

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TEST 5.

Test Number 4 Equipment •Test tube •Test tube rack •Dropper •0.1M AgNO3 silver nitrate solution •Ethanol hydroxide solid KOH •2M HNO3 Nitric acid •Blue litmus paper •Potassium

Procedure
(Alkyl halide test)

1. Add 6 drops of the unknown organic sample into a mixture of 12 drops of ethanol with a little solid KOH potassium hydroxide (the ethanol helped dissolve the KOH) 2. Cool mixture & add 2M HNO3 (nitric acid) until blue litmus paper turns red indicating solution is acidic. 3. Add 7 drops of AgNO3 (silver nitrate) solution.

Observations

The potassium hydroxide was added to the solution and reacted instantly. The solution heated up and bubbled as gas was released. After the potassium hydroxide had completely dissolved, the solution was colourless and miscible. After the solution was made acidic and the AgNO3 silver nitrate solution was added, a white cloudy precipitate formed.

Discussion

This is an Alkyl Halide Test and a precipitate forming is a positive indication that the unknown organic sample is a halo alkane and therefore the unknown organic sample must be dichloromethane. This test works because hallogens on carbon chains are easily displaced by hydroxide ions. An aqueous solution of potassium hydroxide is a good source of hydroxide ions. In step 1, the unknown organic sample was added to a hydoroxide solution & the halogen was displaced. The solution is basic so drops of HNO3 Nitric Acid were added to the solution until it just became acidic. The silver nitrate solution (nitrate because soluble in almost everything) was then added. (Acid+metal → salt+water). The white cloudy precipitate that formed was AgCl.

Families & compounds eliminated

Propanone has now been ruled out as ketones have been eliminated because the unknown organic substance has been found to be an alkyl halide.

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CONFIRMATION TEST

Confirmation Test Equipment •Digital scales •Test tube •50 mL beaker •Bulb pipette

Procedure

1. 2. 3. 4. 5.

Weigh and record the mass of the empty beaker Using the bulb pipette measure 5 mL of the unknown sample Add the 5 mL of the unknown sample to the beaker and record the new mass Work out the mass of the 5mL sample of dichloromethane Compare this mass with the expected mass per 1mL (density)

Mass of empty beaker- 𝟐𝟗. 𝟒𝟑 grams Expected density of dichloroethane per mL- 𝟏. 𝟑𝟐 grams

35.79g − 29.41g = 6.38g per 5mL Results 6.38g = 1.28 grams per mL 5mL 1.32 − 1.28 = 0.04
0.04 1.32

× 100 = 𝟑% difference ( very small )

CONFIRMATION TEST IS POSITIVE FOR DICHLOROMETHANE

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CONCLUSION

The unknown sample was found to be dichloromethane from the functional group haloalkanes. The hypothesis was correct. By following the pre-prepared flow chart and the steps and procedures included in it carefully and as accurately as possible, the unknown organic sample was able to be identified. Flow charts can make identifying unknown chemicals and compounds a much simpler task.

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