Organic Analysis Flashcards

1
Q

How do you test for carboxylic acids? (2)

A
  • Add hydrogen sodium carbonate (NaHCO3).

* Positive result: effervescence- CO2 gas given off.

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2
Q

How does infrared (IR) spectroscopy work? (8)

A
  • A pair of atoms joined by a chemical bond is always vibrating.
  • The system behaves like two balls (the atoms) joined by a spring (the bond).
  • Stronger bonds vibrate faster (at a higher frequency).
  • Heavier atoms make the bond vibrate more slowly (at a lower frequency).
  • Every bond has its own unique natural frequency that is in the IR region of the electromagnetic spectrum.
  • When you shine a beam of IR radiation (heat energy) through a sample the bonds in the sample can absorb energy from the radiation and vibrate more.
  • Any particular bond can only absorb radiation that has the same frequency as the natural frequency of the bond.
  • The radiation that emerges from the sample will be missing the frequencies that correspond to the bonds in the sample.
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3
Q

What happens in the infrared spectrometer? (4)

A
  • 1). A beam of infrared radiation containing a spread of frequencies is passed through the sample.
  • 2). The radiation that emerges is missing the frequencies that correspond to the types of bonds found in the sample.
  • 3). The instrument plots a graph of the intensity of the radiation emerging from the sample, called the transmittance, against the frequency of radiation.
  • 4). The frequency is expressed as a wavenumber, measured in cm^-1.
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4
Q

What is the infrared spectrum? (3)

A
  • A graph in which the dips in the graph represent particular bonds.
  • Helps to identify the functional group present in a compound.
  • Use the data sheet to identify an organic compound.
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5
Q

What is the fingerprint region? (3)

A
  • An area of an infrared spectrum below 1500 cm^-1, which usually has many peaks caused by complex vibrations of the whole molecule.
  • This shape is unique for any particular substance.
  • Used to identify the chemical.
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6
Q

How do chemists use a fingerprint region? (2)

A
  • By using a computer to match the fingerprint region of a sample with those on a database of compounds.
  • An exact match confirms the identification of the sample.
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7
Q

How do you test if you have a primary, secondary or tertiary alcohol? (6)

A
  • 1). Add 10 drops of the alcohol to 2 cm^3 of acidified potassium dichromate solution in a test tube.
  • 2). Warm the mixture gently in a hot water bath.
  • 3). Observe the colour change:
  • Primary alcohol = orange solution goes green as an aldehyde forms.
  • Secondary alcohol = orange solution goes green as a ketone is formed.
  • Tertiary = No visible change.
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8
Q

How do you collect some of the product formed when a primary or secondary alcohol is oxidised? (3)

A
  • 1). Add excess alcohol to 2 cm^3 of acidified potassium dichromate solution in a round bottomed flask.
  • 2). Set up the flask as part of distillation apparatus.
  • 3). Gently heat the flask- the alcohol will be oxidised and the product would be distilled off immediately.
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9
Q

How do you test if you have an aldehyde or a ketone? (5)

A
  • 1). Add 2 cm^3 of Fehling’s or Benedict’s solution to a test tube.
  • 2). Add 5 drops of the aldehyde or ketone to test.
  • 3). Put the test tube in a hot water bath to warm it for a few minutes:
  • Aldehyde = blue solution will give a brick red precipitate.
  • Ketone = no visible change.
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10
Q

Describe the silver mirror test to test for aldehydes and ketones. (6)

A
  • 1). Put 2 cm^3 of 0.10 mol dm^-3 silver nitrate solution in a test tube.
  • 2). Add a few drops of dilute sodium hydroxide solution- a light brown precipitate should form.
  • 3). Add drops of dilute ammonia solution until the brown precipitate dissolves completely = 2Ag(NH3)2OH (aq).
  • 4). Place the test tube in a hot water bath and add 10 drops of the aldehyde or ketone and wait for a few minutes:
  • Aldehyde = silver mirror forms on the walls of the test tube.
  • Ketone = no visible change.
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11
Q

How do you test for alkenes? (5)

A
  • 1). Add 2 cm^3 of the solution that you want to test to a tube.
  • 2). Add 2 cm^3 of bromine water to the test tube.
  • 3). Shake the test tube:
  • Alkene = the solution will decolourise (go from orange to colourless).
  • Not alkene = no visible change.
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12
Q

How do you test for carboxylic acids? (5)

A
  • 1). Add 2 cm^3 of the solution to the test tube.
  • 2). Add 1 small spatula of solid sodium carbonate/solution.
  • 3). If the solution begins to fizz, bubble the pas that it produces through some lime water in another test tube:
  • Carboxylic acid = solution will fizz as CO2 is released.
  • Not carboxylic acid = no visible change.
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13
Q

How do you test for halides? (3)

A
  • 1). Add dilute nitric acid- it removes ions such as carbonates (it would fizz and also produce a white precipitate) that might interfere with the test.
  • 2). Add a few drops of silver nitrate solution (AgNO₃).
  • 3). A precipitate is formed (of the silver halide).
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14
Q

What is the ionic equation used to show the reaction of silver nitrate solution and halides? (3)

A
  • Ag^+(aq) + X^-(aq) —> AgX(s) •X = F^-, Cl^-, Br^- or I^-
  • Silver ions are positive.
  • Precipitate formed of the silver halide.
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15
Q

Does a precipitate form when fluoride is present when AgNO3 is added?

A

•No precipitate is formed.

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16
Q

What colour precipitate is formed when chloride is present when AgNO3 is added?

A

•White precipitate.

17
Q

What colour precipitate is formed when bromide is present when AgNO3 is added?

A

•Cream precipitate.

18
Q

What colour precipitate is formed when iodide is present when AgNO3 is added?

A

•Yellow precipitate.

19
Q

Give the reagents and conditions needed to produce prop-1-ene from 1-bromopropane. (2)

A
  • Reflux 1-bromopropane with KOH or NaOH dissolved in ethanol.
  • Halogen elimination reaction.
20
Q

Give the reagents and conditons needed to produce propan-1-ol from 1-bromopropane. (2)

A
  • Reacting 1-bromopropane with water and KOH or NAOH under reflux.
  • Nucleophilic substitution.
21
Q

What makes of water vapour, carbon dioxide and methane greenhouse gases?

A

•They have bonds that are really good at absorbing infrared energy, so the more of the sun’s UV radiation is re-emitted as IR radiation.

22
Q

The more IR radiation a molecule absorbs…

A

•The more effective they are as greenhouse gases.

23
Q

Explain why infrared spectrometry would not be a suitable technique to use to distinguish between propanal and propanone.

A

•The IR spectra would be similar - they both contain C=O, C-C and C-H bonds.

24
Q

Explain why high resolution mass spectrometry would not be a suitable technique to use to distinguish between propanal and propanone.

A

•The relative molecular masses of the compounds are the same - it could not distinguish between them.

25
Q

What are the precautions to be taken when testing for aldehydes and ketones? (2)

A
  • Wear goggles and lab coat - to prevent irritation to eyes and skin.
  • Use a water bath instead of naked flame - aldehydes and ketones are flammable.
26
Q

Deduce a half equation for the reduction of copper (II) to copper (I).

A

Cu^2+ + e^- —> Cu^-

27
Q

Write the equations of the silver mirror/Tollen’s reagent test for aldehydes. (2)

A
  • Overall: RCHO + [O] —> RCOOH

* Silver mirror ionic: [Ag(NH3)2]^+ + e^- —> Ag + 2NH3 (Ag gets reduce)

28
Q

How do 3-methylbut-1-ene and 2-methylbut-2-ene differ in their IR spectrum?

A

•They have different fingerprint regions.