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12 Chemistry > Chapter 9, 10 and 11: Medicinal Chem > Flashcards

Chapter 9, 10 and 11: Medicinal Chem Flashcards

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1
Q

Carbon - carbon double bonds

A
  1. bromine water test ( qualitatative)
    - if the water goes clear there are double bond
  2. iodine number (quantitative)
    - 1mol of I2 reacts with 1mol of c=c double bonds
    - how much iodine has reacted with 100g of a substance
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2
Q

Testing for hydroxyl groups

A
  1. Oxidation (permangenate or dichromate)
    - k dichromate = alcohol is added to the dichromate, if it turns green it is a primary of secondary alcohol if it turns orange is it a tertiary alcohol
  2. Esterification
    - adding a carboxylic acid to the suposed alcohol, if there is a sweet smell then the unknown is an alcohol
  3. Sodium metal
    - Add sodium metal, if H2 gas is produced then a hydroxly group is present, carboxylic acids will also react

they are all qualitative analysis

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3
Q

Testing for a carboxly functional group

A
  1. Hydrogen carbonate
    - carboxylic acids will react with hydrogen carbonates to produce CO2 gas, which is observed as bubbling, limewater will turn cloudy for further testing.
  2. Esterification
    - A carboxlic acid will create a sweet smell when mixed with an alcohol.
  3. pH
    - an acid base indicator like phenolphthalein, can detect a change in pH, partially ionising in water producing H+ ions, if a weak acid is preset, then its likey to be a carboxlyic acid.

they are all qualitative analysis

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4
Q

Analysis of mixtures

A

is not the functional group testing as they are pure not a mixture.

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5
Q

Melting point

A

melting point determination
- the identification of a compound by comparison of an experimental melting point value to a literature value, and the purity of a sample to be measured.
- Impure samples have a wider and lower melting point range than pure samples of the same substance
- To confirm the identify of an unknown compound, the experimental sample can be mixed with a known substance in a 1:1 ratio

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6
Q

Boiling point

A

Distillation
1. Simple
- Simple distillation involves heating a mixture to a target temperature to vaporise the components to be separated. Vapour fractions are condensed and collected.
2. Fractional
- i know this one, temperature gradient, making them pure

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7
Q

Spectroscopy

A
  1. Infrared
  2. NMR
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8
Q

Infrared Spectroscopy (IR)

A
  • vibration of covalent bonds by IR radiation.
  • the upside down graphs, the O-H looks big and wide
  • allows identification of the functional groups and single, double and triple bonds in organic molecules
  • identifies the specific energy absorbed by the various covalent bonds
  • below 1500 is the fingerprint region, containing a pattern of peaks individual for an individual molecule.

qualitative analysis

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9
Q

NMR Spectroscopy

A
  • NMR is a qualitative analysis method used to determine molecular structure
  • NMR utilises a property of certain nuclei called ‘spin’ to identify the location of atoms within a molecule. Nuclei with an odd number of nucleons can be detected by NMR, as they have two overall spin states (e.g. 1H and 13C).
  • Radio waves are provided to change the spin state of the nuclei, which can then be detected.
  • Electrons surrounding a nucleus will somewhat shield it from the applied magnetic field of an NMR spectrometer. As such, the radio wave energy required to change the spin state of nuclei differs depending on the extent of shielding.
  • tetramethylsilane (TMS). The value for the TMS signal is set to zero
  • n + 1 rule
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10
Q

Spectrometry

A
  1. only mass spectrometry
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11
Q

Mass Spectrometry

A

FRAGMENTATION = [CH3]+
- Base peak is the tallest one
- Parent peak is the M of the molecular ion
- m/z thing
- The isotope effect can explain the presence of multiple peaks for fragments with the same formula due to the presence of isotopes of the constituent elements.
- Fragment destoryed in the process

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12
Q

m/z

A

 the ratio of the mass of an ion relative to its charge

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13
Q

Relative abundance

A

 the abundance/intensity of an ion relative to the base peak

  • mass spec
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14
Q

Chromatography

A
  • Chromatography is a technique used to separate components of a mixture. Once separated, the components can be identified (qualitative analysis) and their concentration in the sample determined (quantitative analysis).
  • Mobile phase and stationary phase, opposite polar or non-polar
  • Components are detected as they exit the column and recorded as a series of peaks on a chart called a chromatogram, including both the retention time, Rt, and area of each peak.
  • Retention time can be used to identify a component, by comparing the retention time for an unknown substance with those for known substances under the same operating conditions.
  • can use results to make a calibration curve
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15
Q

Stereoisomers

A

the atoms are connected in the same order but are oriented differently in space. As a result, stereoisomers tend to have different chemical properties.
- same atom to atom bond but oriented differently in space

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16
Q

Optical isomers

A

are non-superimposable mirror images of each other, known as enantiomers.

17
Q

Enantiomers

A
  • A molecule will form enantiomers if it contains a chiral centre, which is a carbon atom bonded to four different atoms, or groups of atoms.
  • Enantiomers are known as optical isomers because polarised light is rotated when it is passed through a sample containing the chiral compound.
18
Q

Enantiomers in medicince

A

Laboratory synthesis of optically active substances generally produces a mixture of the two enantiomers. By contrast, stereoisomers formed in biological systems consist of only one enantiomer. As a result of this, many of the natural and synthetic drugs used in medicine have different effects on the body. This is because the enantiomer in the body has a unique three-dimensional shape so the drug that interacts (binds) with it must have a matching three-dimensional shape

19
Q

Extraction and purification of medicines sourced from plants

A
  • Distillation separates substances based on differences in volatility.
  • Solvent extraction is a technique to separate solutes based on their relative solubility in two solvents with different polarity.
  • The yield of solvent extraction may be improved by repeatedly extracting the original solution with fresh solvent, and the resultant fractions combined.
  • Sample purity may be improved by using distillation to provide additional separation
20
Q

volatility

A

volatility describes how readily a liquid substance will form a vapour

21
Q

Chiral compound

A

 compound with a non-superimposable mirror image

22
Q

Chiral centre

A

 carbon atom in a compound attached to four unique chemical environments

23
Q

Optical isomers

A

two non-superimposable mirror images of the same compound

24
Q

Racemate

A

an approximately 50/50 mixture of a chiral compound’s two optical isomers,
which does not rotate polarised light in a specific direction

25
Q

Purity

A

mass of particular substance / mass of sample x 100

26
Q

Solvent extraction

A
  • molecules are non polar in a polar solvent
  • non polar solvent is added
  • shake up
  • the non-polar bits will go into the non-polar solute, like disolves like
  • separate them through evaporation or distillation.
27
Q

Enzyme-catalysed reactions are stereospecific

A

such that only substrates with the correct shape will fit into the active site.

28
Q

Enzymes

A
  • Enzymes are protein-based catalysts that increase the rate of reactions in biological systems.
  • Each enzyme generally catalyses one specific reaction or a series of closely related reactions sharing a functional group, so there are many different enzymes working in our bodies.
29
Q

Amino Acids in alkaline

A
  • In solutions of high pH (alkaline)
  • Acting as an acid
  • donation of protons
30
Q

Amino Acids in acidic

A
  • In solutions of low pH (acidic)
  • Acting as a base
  • acceptance of protons
31
Q

zwitterion

A

a molecule with a net charge of zero but negative and positive charges on individual atoms in its structure, they have the COO- and the NH3+

32
Q

Primary

A

peptide bonds, order of amino acids

33
Q

secondary

A

hydrogen, arrangments of amino acids into a helix and b pleated sheets

34
Q

tertiary

A

hydrogen, ionic, covalent, dispersion, disulfide bridges, overall 3D functional shape and the protein is now functional

35
Q

quaternary

A

dispersion, hydrogen, one or more polypeptide chains combined

36
Q

coagulation

A

the process of turning a liquid into a solid or a thicker liquid

37
Q

Endpoint

A

when the colour change is permenant

38
Q

Equivalence point

A

when the reactants are in their exact stoichiometric ratio.

12 Chemistry (6 decks)

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