Organic Compound Differentiation Tests
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Questions and Answers

Which of the following observations would indicate a positive result for the Tollen's test when performed on an unknown organic compound?

  • No observable change.
  • Decolorization of bromine water.
  • Formation of an orange-red precipitate.
  • Formation of a silver mirror. (correct)

Which of the following correctly describes the expected outcome of a Lucas test on a secondary alcohol?

  • Turbidity forms within approximately 5 minutes. (correct)
  • No turbidity at room temperature.
  • Immediate turbidity.
  • Formation of a precipitate soluble in NaOH.

A researcher performs a Hinsberg test on an unknown amine and observes that a precipitate forms, which is insoluble in NaOH. Which type of amine is most likely present?

  • Primary amine.
  • Tertiary amine.
  • Quaternary ammonium salt.
  • Secondary amine. (correct)

Which of the following observations would differentiate phenol from benzoic acid using a neutral FeCl3 test?

<p>Phenol produces a violet color, while benzoic acid produces a buff color. (A)</p> Signup and view all the answers

Which of the following correctly matches the organic compound to its expected observation in the Bromoform test?

<p>CHCl3; Pale yellow precipitate of AgI (A)</p> Signup and view all the answers

A researcher observes no reaction when adding sodium bicarbonate (NaHCO3) to an unknown liquid sample. Which of the following compounds can be ruled out as a major component of the sample?

<p>Acetic acid (C)</p> Signup and view all the answers

A chemist performs the iodoform test on two unknown samples. Sample A yields a yellow precipitate, while Sample B shows no observable change. Based on these results, what can be concluded about the original composition of Sample A?

<p>Sample A contains a compound that can be oxidized to a methyl ketone. (C)</p> Signup and view all the answers

Which of the following pairs of compounds can be best distinguished by observing the formation of a silver mirror when Tollen's reagent is added and heated?

<p>Acetic acid and formic acid (B)</p> Signup and view all the answers

A laboratory technician adds neutral Iron(III) chloride (FeCl3) to two separate samples. Sample 1 turns wine red, while sample 2 turns violet. Which pair of compounds is most likely present in Sample 1 and Sample 2, respectively?

<p>Acetic acid and Phenol (C)</p> Signup and view all the answers

A researcher is trying to identify an unknown compound. Upon adding chloroform (CHCl3) and alcoholic potassium hydroxide (KOH) to the compound, a foul odor is detected. Which of the following functional groups is most likely present in the unknown compound?

<p>Amine (C)</p> Signup and view all the answers

Consider two compounds: aniline and dimethyl aniline. Which of the following observations from a carbylamine test would best distinguish between them?

<p>Aniline will produce a foul-smelling carbylamine, while dimethyl aniline will not react. (B)</p> Signup and view all the answers

A student performs Fehling's test on an unknown compound and observes the formation of an orange-red precipitate. Based on this observation, which of the following functional groups is most likely present in the unknown compound?

<p>Aldehyde (D)</p> Signup and view all the answers

Which of the following reagents would be most suitable for differentiating between acetic acid and phenol based on a color change?

<p>Neutral FeCl3 (D)</p> Signup and view all the answers

A chemist has two unlabeled compounds, acetophenone and benzophenone. Which of the following tests would conclusively differentiate between them?

<p>Iodoform test, looking for the formation of a yellow precipitate. (B)</p> Signup and view all the answers

Two unknown liquids are suspected to be either 2-pentanone or 3-pentanone. Which test would definitively identify which liquid is which?

<p>Performing an iodoform test and observing for a yellow precipitate. (B)</p> Signup and view all the answers

Acetaldehyde and acetone can both be oxidized, but require different reagents to do so. Which of the following options correctly describes a test that differentiates them based on this difference?

<p>Only acetaldehyde will react with Tollen’s reagent, forming a silver mirror. (D)</p> Signup and view all the answers

To distinguish between acetaldehyde and benzaldehyde, a student proposes using both Fehling's test and the iodoform test. Why is this a suitable approach?

<p>Fehling’s test confirms acetaldehyde, while the iodoform test confirms acetaldehyde also. (B)</p> Signup and view all the answers

A chemist needs to differentiate between acetaldehyde and formaldehyde in the lab. Which single test will help them distinguish the two compounds effectively?

<p>Iodoform test. (C)</p> Signup and view all the answers

A lab technician is given two unlabeled samples: acetamide and ethylamine. Which of the following tests would best differentiate them based on their chemical properties?

<p>The carbylamine test. (B)</p> Signup and view all the answers

Consider two organic compounds, $CH_3COCH_3$ (acetone) and $CH_3CHO$ (acetaldehyde). Which statement accurately describes how to differentiate them using a simple chemical test?

<p>Only acetaldehyde will react with iodine in the presence of base to give a yellow precipitate. (B)</p> Signup and view all the answers

You have two unlabeled containers, one containing propanal and the other propanone (acetone). Which of the following tests will best distinguish between these two compounds?

<p>Performing a Tollen's test; propanal will give a positive result. (D)</p> Signup and view all the answers

In a diazotization-coupling reaction, aniline is treated with cold $NaNO_2$ and concentrated $HCl$, followed by phenol. What is the major product of this reaction, and what observable change would confirm its formation?

<p>p-hydroxyazobenzene, indicated by the formation of an orange-red color. (A)</p> Signup and view all the answers

Which of the listed pairs of compounds can be distinguished using the Iodoform test?

<p>Acetone and Diethyl ether (B), Ethanol and Phenol (C)</p> Signup and view all the answers

A chemist has two unknown compounds. One gives a positive result to both Fehling's test and Schiff's test, while the other gives negative results for both tests. Which of the following pairs of compounds could they be?

<p>Acetaldehyde and Benzaldehyde (B)</p> Signup and view all the answers

Tollen's reagent is used to distinguish between which of the following pairs of compounds based on the formation of a silver mirror?

<p>Benzaldehyde and Nitrobenzene (D)</p> Signup and view all the answers

Which of the following compounds will restore the pink color of Schiff's reagent after it has been decolorized?

<p>Acetaldehyde (C)</p> Signup and view all the answers

A student performs the iodoform test on two unknown liquid samples. Sample A gives a positive result, while sample B gives a negative result. If sample A is known to be an alcohol, which of the following could it be?

<p>Ethanol (D)</p> Signup and view all the answers

A chemist has two unlabeled containers, one with ethanol and the other with diethyl ether. Which of the following tests would allow the chemist to correctly label the containers?

<p>Iodoform test (B)</p> Signup and view all the answers

When testing an unknown compound, a student performs the iodoform test and observes the formation of a yellow precipitate. Which functional group is most likely present in the unknown compound?

<p>Methyl ketone (D)</p> Signup and view all the answers

Flashcards

Iodoform Test

A reaction that produces a yellow precipitate of iodoform when iodine and sodium hydroxide are added to a compound containing a methyl ketone or secondary alcohol with a methyl group in the alpha position.

Tollen's Test

Distinguishes between aldehydes and ketones using ammoniacal silver nitrate, forming a silver mirror with aldehydes.

Fehling's Test

Tests for aldehydes using alkaline copper sulfate and sodium potassium tartrate, forming an orange-red precipitate with aldehydes.

Acetophenone vs. Benzophenone

Acetophenone gives a positive iodoform test (yellow precipitate), while benzophenone does not.

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2-Pentanone vs. 3-Pentanone

2-Pentanone gives a positive iodoform test (yellow precipitate), while 3-pentanone does not.

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Acetaldehyde vs. Acetone

Acetaldehyde gives a positive Tollen's test (silver mirror) while acetone does not.

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Acetaldehyde vs. Benzaldehyde (Fehling's Test)

Acetaldehyde forms an orange-red precipitate with Fehling's reagent, while benzaldehyde does not.

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Carbylamine Test

The reaction of a primary amine with chloroform and a base to form an isocyanide, which has a foul odor.

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Br2 Water Test

A test to detect aldehydes and aromatic alcohols. Positive result indicated by white precipitate of 2,4,6-tribromophenol.

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Lucas Test

Used to determine the type of alcohol. Primary: no immediate turbidity; Secondary: turbidity in 5 mins; Tertiary: immediate turbidity.

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Hinsberg Test

Used to classify amines. Primary: precipitate soluble in NaOH; Secondary: precipitate insoluble in NaOH; Tertiary: no precipitate.

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NaHCO3 Test: Positive Result

Effervescence (bubbles) indicates a reaction; lime water turns milky.

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Fehling's Test: Positive Result

Orange-red precipitate (ppt) of Cu2O forms, indicating an aldehyde group.

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Tollen's Reagent Test: Positive Result

Silver mirror forms on the test tube walls, indicating an aldehyde group.

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Neutral FeCl3 Test: Acetic Acid

Wine red coloration indicates the presence of an acid.

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Neutral FeCl3 Test: Phenol

Violet color indicates the presence of a phenol group.

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Carbylamine Test: Positive Result

Foul smelling carbylamine indicates the presence of a primary amine.

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Iodoform Test: Positive Result

Formation of a yellow precipitate of iodoform.

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neutral FeCl3 test: Positive Result

Brown color forming.

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Diazotization-Coupling Reaction

A reaction where an aromatic amine reacts with nitrous acid to form a diazonium salt, followed by a reaction with another aromatic compound.

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Tollen's Reagent Test

A chemical test used to distinguish between aldehydes and ketones, where Tollen's reagent oxidizes aldehydes to form a silver mirror on the test tube wall.

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Schiff's Reagent Test

A reagent used to test for aldehydes; aldehydes restore the magenta color of Schiff's reagent after it has been decolorized by sulfur dioxide.

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Ethanol and Iodoform

Ethanol is unique among alcohols because it gives a positive result in the Iodoform test due to its oxidation to acetaldehyde.

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Positive Iodoform Test Result

A test using iodine and sodium hydroxide to detect methyl ketones and certain alcohols (like ethanol) which produce a yellow precipitate of iodoform.

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Distinguishing Ethanol from Phenol

The Iodoform test differentiates between ethanol and phenol; ethanol gives a positive result (yellow precipitate), while phenol does not.

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Study Notes

  • These notes summarize tests used to differentiate between organic compounds.

Experiment 1: Iodoform Test

  • To the sample, iodine and sodium hydroxide are added, then heated in a water bath.
  • Acetophenone yields a yellow precipitate of iodoform.
  • Benzophenone exhibits no characteristic observation.

Experiment 2: Iodoform Test

  • To the sample, iodine and sodium hydroxide are added, then heated in a water bath.
  • 2-pentanone yields a yellow precipitate of iodoform.
  • 3-pentanone exhibits no characteristic observation.

Experiment 3

Tollen's Test (A)

  • To the sample, ammoniacal silver nitrate is added and heated in a water bath.
  • Acetaldehyde forms a silver mirror on the inner walls of the test tube.
  • Acetone/propanone exhibits no characteristic observation.

Fehling's Test (B)

  • To the sample, alkaline copper sulphate and sodium potassium tartrate are added, then heated in a water bath.
  • Acetaldehyde forms an orange-red precipitate of Cu2O.
  • Acetone/propanone exhibits no characteristic observation.

Experiment 4

Fehling's Test (A)

  • To the sample, alkaline copper sulphate and sodium potassium tartrate are added, then heated in a water bath.
  • Acetaldehyde forms an orange-red precipitate of Cu2O.
  • Benzaldehyde exhibits no characteristic observation.

Iodoform Test (B)

  • To the sample, iodine and sodium hydroxide are added, then heated in a water bath.
  • Acetaldehyde yields a yellow precipitate of iodoform.
  • Benzaldehyde exhibits no characteristic observation.

Experiment 5: Iodoform Test

  • To the sample iodine and sodium hydroxide is added and heated in a water bath.
  • Acetaldehyde yields a yellow precipitate of iodoform.
  • Formaldehyde exhibits no characteristic observation.

Experiment 6: Carbylamine Test (A)

  • To the sample, CHCl3 and alcoholic KOH added, then warmed in a water bath.
  • Acetamide has no characteristic observation.
  • Ethylamine has a foul smelling carbyl amine formed.

Experiment 7: With NaHCO3

  • To the sample NaHCO3 is added.
  • Acetic acid causes brisk effervescence that turns lime water milky.
  • Acetone exhibits no characteristic observation.

Iodoform test

  • Added iodine and sodium hydroxide and heated in a water bath.
  • Acetic acid has no characteristic observation.
  • Acetone yields a yellow precipitate of iodoform.

Experiment 8

Fehling's test (A)

  • Alkaline copper sulphate and sodium potassium tartrate is added and heated in a water bath.
  • Acetic acid has no characteristic observation.
  • Formic acid yields an orange-red precipitate of Cu2O.

Tollen's reagent (B)

  • Ammoniacal silver nitrate is added and heated in a water bath.
  • Acetic acid exhibits no characteristic observation.
  • Formic acid forms a silver mirror on the inner walls of the test tube.

Neutral FeCl3 test (C)

  • Neutral FeCl3 is added and warmed in a water bath.
  • Acetic acid has a wine-red coloration
  • Formic acid has a brown colour

Experiment 9

With neutral FeCl3 test (A)

  • To the sample added neutral FeCl3 and warmed in a water bath.
  • Acetic acid yields wine red color from ferric acetate.
  • Phenol yields violet color of iron phenoxide.

With NaHCO3 test (B)

  • Add to the sample NaHCO3
  • Acetic acid gives brisk effervescence.
  • Phenol has no characteristic observation.

Experiment 10

Carbylamine test (A)

  • To the sample added CHCl3 and alcoholic KOH.
  • Aniline yields a foul smelling carbyl amine.
  • Phenol has no characteristic observation

Experiment 11

Carbylamine Test

  • Add to the sample CHCl3 and alcoholic KOH and warm it in a water bath.
  • Aniline yields a foul smelling carbyl amine.
  • Dimethyl aniline has no characteristic observation.

Experiment 12: Diazotisation-Coupling Reaction

  • To the sample, add cold NaNO2 and conc HCl followed by phenol between 0-5 degrees C.
  • Aniline yields an orange-red color of p-hydroxy azo benzene.
  • Ethylamine has no characteristic observation.

Experiment 13

Iodoform Test (A)

  • Added iodine and sodium hydroxide and warm it in a water bath.
  • Benzaldehyde has no characteristic observation.
  • Acetaldehyde yields a yellow precipitate of iodoform.

Fehling's Test (B)

  • Add alkaline copper sulphate and sodium potassium tartrate and heat in a water bath.
  • Benzaldehyde has no characteristic observation.
  • Acetaldehyde yields an orange-red precipitate of Cu2O.

Experiment: 14

Tollen's reagent:

  • Benzaldehyde has no observation noted.
  • Nitrobenzene has no observation noted.

Experiment: 15, Iodoform test

  • Acetone yields yellow ppt of iodoform.
  • Diethyl ether has no characteristic observation.

Experiment: 16, Iodoform test

  • Ethanol, and it is the only alcohol which gives a positive iodoform test, and has a yellow ppt of iodoform.
  • Diethyl ether has no characteristic observation.

Experiment: 17

Iodoform Test (A)

  • Ethanol reacts giving yellow ppt of Iodoform.
  • Phenol has no characteristic observation .

Br2 water test (B)

  • Ethanol has no characteristic observation noted.
  • Phenol shows a white ppt of 2,4,6 tribromophenol.

Experiment: 18

Tollen's Test (A)

  • Glucose creates silver mirror. Success has no characteristic observation.

Fehling's Test (B)

  • Glucose creates orange red ppt of Cu2O.
  • Success has no characteristic observation

Experiment: 19 Bromine water test

  • Both decolourises the red color of Bromine for Glucose and Fructose, and reacts to both Tollens and Fehlings reagents.

Experiment: 20, Add AgNO3 to both the samples

  • Glucose has no characteristic observation noted with CHCl3.
  • Fructose creates a pale yellow ppt of Agl from CHI3.

With Neutral FeCl3 Test

  • Benzoic acid yields a buff color.
  • Phenol yields a violet color.

Experiment: Lucas test

  • Primary alcohol exhibits no turbidity at ordinary temperatures.
  • Secondary alcohol exhibits turbidity within 5 min.
  • Tertiary alcohol exhibits turbidity within seconds.

Experiment: Hinsberg test

  • Primary amines form precipitate is formed is soluble in NaOH.
  • Secondary amines exhibit precipitate, but it is insoluble in NaOH.
  • Tertiary amines form no precipitate.

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Description

Summary of tests used to differentiate between organic compounds, including the iodoform, Tollen's, and Fehling's tests. Reactions with acetophenone, benzophenone, 2-pentanone, 3-pentanone, acetaldehyde, and acetone are described. Includes observations for each reaction.

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