how are organic compounds analysed and used?

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59 Terms

1
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testing for C=C bonds

  • bromine water test

  • iodine number

2
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bromine water test

  • unsaturated compound + Br2 → brominated product (addition reaction)

    • orange/brown → colourless

  • saturated compound + Br2 → no reaction

    • orange/brown colour persists

3
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iodine number

m (I2) reacts with 100g chemical substance

  • 1 mol of I2 = 1 mol of C=C

4
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testing for hydroxyl groups

  • sodium metal test

  • oxidation test

  • esterification test

5
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sodium metal test

  • if sample is alcohol, mixing it with Na (s) will create H2 (g)

  • pop test to confirm

6
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oxidation test

  • primary alcohol → oxidising agent (Cr2O72-/H+) (low temp) aldehyde → oxiding agent (Cr2O72-/H+) (high temp) carboxylic acid

    • orange → green

  • secondary alcohol → oxidising agent (Cr2O72-/H+) ketone

    • orange → green

  • tertiary alcohol → no reaction

    • orange persists

7
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esterification test

  • if fruity smell detected, ester is produced

8
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testing for carboxyl group

  • pH test

  • metal hydrogen carbonate test

  • esterification test

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pH test

  • acid-base indicators

  • carboxylic acids are weak and only partially ionise

  • ↑ [H+]/[H3O+], ↑ acidity, ↓ pH

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metal hydrogen carbonate test

  • if sample is a carboxylic acid, mixing it with HCO3- will produce CO2 (g)

  • can confirm it is CO2 (g) if it turns limewater cloudy

11
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melting point determination

  • allows for identification of compound by comparing with literature value

  • purity of compounds can be determined

12
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simple distillation

  1. mixture heated to target temp to vaporise component to be seperated

  2. vapour passes through condenser

  3. distillate obtained

  • cannot seperate compounds with similar BP

13
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fractional distillation

  1. mixture heated to target temp to vaporise component to be seperated

  2. vapour moves up the fractionating column, some condenses & flows down until hot enough to vaporise again

  3. after each boil-condense cycle, the more volatile substance will be at the top

  4. vapour passes through condenser

  5. distillate obtained

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features of the fractionating column

  • colder at the top

  • glass beads to increase surface area

15
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standard solution

solution with accurately known concentration by dissolving water & a primary standard

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primary standard

substance with high purity & stability

17
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what is the volumetric glass rinsed with?

distilled water

18
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what is the conical flask rinsed with?

distilled water

19
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what is the volumetric pipette rinsed with?

substance it will deliver

20
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what is the burette rinsed with?

substance it will deliver

21
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what is the volumetric flask used for?

prepare standard solution

22
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what is the conical flask used for?

hold the aliquot of solution that will be titrated

23
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what is the volumetric pipette used for?

deliver an aliquot of a solution

24
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what is the burette used for?

deliver the solution

25
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equivalence point

two reactants have reached correct mole proportions

  • estimated by the end point

26
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end point

permanent colour change

27
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mass spectrometry

investigation and measurement of masses of isotopes, molecules and molecular fragments by ionising samples & seperating fragments produced using electric and magnetic fields

  • only positively charged ions detected

  • measures the mass-to-charge ratio (m/z) of particles

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ionisation

  • generates molecular ion by bombarding sample with high energy e-

  • M (g) + e- → M+ (g) + 2e-

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fragmentation

  • unstable molecular ions produce a variety of smaller ions as bonds are broken

  • fragmentation pattern can help determine structure of original molecule

30
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molecular ion

positive ion produced by ionisation of a whole molecule

31
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the isotope effect

generation of multiple peaks for fragments with the same formula due to presence of isotopes of constituent elements

32
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infrared (IR) spectroscopy

measures vibration of atoms in a molecule and gives information on functional groups present

  • infrared radiation change vibrational energy in covalent bonds

  • each type of covalent bond absorbs different wavelengths of infrared radiation

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vibration of covalent bonds

  • ‘ground state’

  • ‘excited-state’

34
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fingerprint region

region below 1500cm-1 containing a pattern of peaks specific for an individual molecule

35
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factors affecting bond vibration energy

  • strength of bonds

  • mass of atom

36
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strengths of bonds

  • stronger bonds require more energy to change their vibration

    → higher frequency, higher wave number

37
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mass of atom

  • bonds between lighter atoms require more energy to change their vibration

    → higher frequency, higher wave length

38
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fundamentals of NMR spectroscopy

  • measures change in spin state of nuclei, which gives information on number of chemical environments

  • involves absorption of radio waves, chemical shift alters with neighbouring environments

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shielding & chemical environments

  • e- surrounding the nucleus will shield it from magnetic field

  • nuclei connected to the same atoms are in the same chemical environment

    → produce one NMR signal

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chemical shift

horizontal scale on an NMR spectrum

  • represents difference in energy required to flip a nucleus in a sample compared to TMS

41
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TMS

  • all NMR produced are compared to a sample (TMS)

  • added to samples prior to analysis, producing single peak for 1H- & 13C-NMR

  • value for TMS set to 0 & position of signal generated is known as chemical shift

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advantages of TMS

  • signal peak away from other peaks

  • volatile, easily recovered

  • allows data from different NMR spectrometers to be compared

43
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low-resolution proton NMR

includes:

  • number of peaks indicate the number of unique hydrogen environments

  • chemical shift provides information about specific environments

44
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high-resolution proton NMR

  • number of peaks indicate the number of unique hydrogen environments

  • chemical shift provides information about specific environments

  • ratio of areas under peaks shows ratio of hydrogen atoms in that environment

  • n+1 rule

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n+1 rule

peak splitting pattern is one more than number of hydrogen atoms on neighbouring carbons

46
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low-resolution carbon NMR

includes:

  • number of peaks indicate the number of unique carbon environments

  • chemical shift provides information about specific environments

47
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stationary phase

solid onto which the components of a sample adsorb

48
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mobile phase

liquid/gas that flows through a chromatography system, moving the materials to be seperated at different rates over the stationary phase

49
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chromatography

  • components go through adsorption to stationary phase & desorption back to mobile phase

  • mobile & stationary phase must be two different polarites

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adsorption

sticking/adhering to the surface

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desorption

removal of a substance from a surface

52
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affinity

attraction of a component to the mobile/stationary phase

53
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retention time (Rt)

time taken for component in a sample to travel from the injection port to end of the column

54
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factors affecting retention time

  • polarity of mobile/stationary phases

  • temperature

  • viscosity of mobile phase

  • pressure applied

  • length of column

55
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polarity of mobile/stationary phase

  • changing will affect relative affinity of a component

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temperature

  • higher temperature increases time component spends in mobile phase, reducing Rt

  • reduce viscosity of mobile phase

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viscosity of mobile phase

  • lower viscosity will increase rate mobile phase flows through, reducing Rt

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pressure applied

  • higher pressure will increase rate of mobile phase flow, reducing Rt

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length of column

  • shorter column will reduce time required for component to exit, reducing Rt