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IDM > TBL 5 - SYNTHESIS OF DRUGS > Flashcards

TBL 5 - SYNTHESIS OF DRUGS Flashcards

1
Q

What is electronegativity?

A

Electronegativity - the power of an atom in a molecule to attract electrons to itself.

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2
Q

Who looked at the nature of chemical bonds?

A

Linus Pauling: the nature of chemical bond

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3
Q

What is dipole moment?

A

Dipole moment: dipole moment is equal to the magnitude moment time distance of the charges. U = Qd - unit of debytes = d

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4
Q

What are intermolecular forces?

A

Are forces between molecules

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5
Q

What is a nucleophile?

A
  • Nucleophile - nucleus loving and has region of high electron density
  • Nucleophile has a full negative charge of partial negative charge
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6
Q

What is alcohol dehydrogenated?

A

Alcohol dehydrogenated is an aldehyde

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7
Q

What happens when carbonyl is bonded with a hydroxyl?

A

If we have a carbonyl bonded with hydroxyl it’s a carboxylic acid

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8
Q

What is carbonyl acid apart of?

A

carbonyl acid is the acid part of amino acid which makes up proteins

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9
Q

What is the simplest carboxylic acid?

A

Simplest carboxylic acid is formic acid makes fire ant bites burn

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10
Q

What is an example of acetic acid?

A

Acetic acid e.g. vinegar

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11
Q

What does pure organic compounds contain?

A

Organic compounds containing only C and H

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12
Q

What are single bonded hydrocarbons known as?

A

Single bonded hydrocarbons are known as saturated hydrocarbon

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13
Q

What are alkanes?

A

Alkanes: are fully saturated hydrocarbons have single bonds e.g. methane, ethane, propane, butane - 2 forms of butane n-butane and i-butane, i-butane is carbon chain with one chain branched off the carbon center.

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14
Q

What are isomers?

A
  • Isomer: molecules that have the same molecular formula but different structures.
    • Meth indicates one carbon atom
    • Eth indicated 2 carbon atoms
    • But indicates 4 carbon atoms
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15
Q

How are alkanes named?

A

Alkanes are always named based on the longest possible chain in their structure
Di and tri can be used in the name of structures depending on the number of attachments

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16
Q

What are the 3 types of alkane reactions?

A

1) Combustion - burning - requires a hydrocarbon, O and source of heat energy products of reaction would be CO2 and water vapor
2) Halogenation - replacement of hydrogen atoms with halogens e.g. F, Cl
3) Dehydrogenation - removal of water molecule - H atoms

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17
Q

How do you rank functional groups?

A

1) Identify the hydroxyl group is there
2) Identify where it is
3) Identify if there is a double bond

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18
Q

What is chemical equilibrium?

A
  • 2 molecules can join and become 1, 1 can spit apart and become 2 - these changes known as chemical reactions.
  • Molecules need to hit each other hard and in the right orientation
  • Most reactions happens in both directions
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19
Q

What are alkanes and what are single bonds known as?

A
  • Saturated hydrocarbons, single bonds only.
  • single bonds are known as sigma bonds, when carbon atoms attached by them can rotate around the bond freely.
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20
Q

What are alkenes and what do double bonds consist of?

A
  • Unsaturated hydrocarbons, double bonds.
  • Double bonds consist of a sigma bond and a pi bond. Pi bonds bridges the sigma bond locking it into place. So whatever is attached on the other side of the carbon atoms can’t change their orientation with respect to each other.
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21
Q

What is the difference between the cis and trans?

A

Cis: same side, Trans: on different sides

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22
Q

What are alkyne and what types of bonds is it composed of?

A
  • Unsaturated hydrocarbons, triple bonds.
  • Triple bonds composed of 1 sigma bond and 2 pi bonds for a total of 3 bonds.
  • Pi bonds prevent the triple bonds from rotating, but triple bonded carbons can only bond to one other atom, so even if it could rotate nothing would change.
  • No isomers with alkynes
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23
Q

Why can double and triple bonds easily break?

A

Pi bonds more unstable than sigma bonds, so double and triple bonds can easily break.

24
Q

What are additional reactions?

A

Certain reactions can open up a double or tiple bond to insert various atoms leaving only a single bond between carbons. These are called addition reactions cus atoms are added to the carbons that were previously double bonded.

25
Q

What are hydrogenation?

A

Hydrogenation - simplest addition reactions in which a molecule of H2 is added across the bond. To do this a metal catalyst like platinum is usually required to help break the H2 apart, cus the bond is very strong. Once it’s done the H atoms readily attach the hydrocarbon molecule converting a double bond to a single bond.

26
Q

What is halogenation?

A

Other molecules can break the double bond as well such as bromine added in place of hydrogen, the reaction is called HALOGENATION

  • Water molecule added - hydration
  • Oxygen gas added - oxygenation
27
Q

What is triglyceride?

A

Triglyceride: 3 fatty acids attached to a molecule of glycerol

28
Q

What is a fatty acid chain?

A

Fatty acid chains - have long hydrocarbon chains - most common are alkanes/alkenes, rarely alkynes

29
Q

What are saturated fats?

A
  • no double bonds only single bonds making it an alkane and has many H atoms.
  • Means no unstable pi bonds so have a longer shelf life, can lay flat against each other making them more likely to be solid at room temp.
30
Q

Why are saturated fats hard to break down in your body?

A

Means it’s harder for your body to break them down as they’re very stable so often stick around in the body clogging vessels up

31
Q

Why are vegetable oils poly-unsaturated fats?

A

Vegetable oils are poly-unsaturated fats so has lots of double bonds

32
Q

Why are vegetable oil heathier and cheaper then saturated fats?

A

Healthier and cheaper then saturated fats as saturated fats come from animals

33
Q

In what state is vegetable oils at room temp?

A

Its less stable and usually liquid at room temp.

34
Q

How do food chemist use hydrogenation?

A

Food chemist use hydrogenation to saturate the unsaturated fat, making it spreadable and also stabilizing. Since its made from vegetable oil instead of animal product its cheaper to create.

35
Q

What does fully hydrogenated oils create?

A

Oils can be fully hydrogenated creating saturated alkanes.

36
Q

What happens during partially hydrogenated oils?

A

Sometimes partially hydrogenated leaving 1 double bond in fatty acid chain creating a mono-unsaturated fat.

Location of double bonds also has an effect on what your body can do with the molecules leads to omega-3

Omega-3 refers to specific location of double bond - 3 carbons from the end or omega of the fatty acid chain, body is incapable of making this sort of fatty acid but need them to survive - have to eat them.

37
Q

What are trans-fats and cis-fats and how trans-fats broken down into?

A
  • Unsaturated alkenes
  • Really bad - all natural unsaturated fats are cis-fasts which our bodies are prepared for and know what to do with
  • Trans-fats created by partially hydrogenated vegetable oil
  • Body system can break down trans-fats into healthy by-products
38
Q

What are Le Chatelier principles?

A

When a chemical system at equilibrium is stressed, the system works to restore equilibrium this is le chateliers principle

39
Q

What stresses can affect equilibrium?

A

Stresses are:
-Changes in concentration of either the reactants or products
-Changes to the pressure applicant to gas
-Changes in temp

40
Q

How can you counteract the stresses for the equilibrium?

A
  • To counteract the stress add an equal amount on either side of chemical reactions.
  • When conc increased, equilibrium shifts to opposite side of reaction
  • When conc decreases, shifts to the same side of the reaction
41
Q

What happens when there is an increase and decrease in pressure (Hint: moles)?

A

Equilibrium will shift to the side of the reaction with fewer moles.
- Increase in pressure favors side with fewer moles
Decrease in pressure favors side with more moles.

42
Q

Why do organic reactions happen?

A
  • Molecules/atoms react cus they can move.
  • In liquid or gas form, whole molecules move around continuously.
  • If different molecules mixed together they continuously bump into each other.
  • If collisions aligned (where their electronic orbitals overlap) and these collisions have sufficient energy, a bond if formed to give a new molecule
43
Q

5 types of organic reactions:

A
  • Addition reactions
  • Elimination reactions
  • Substitution reactions
  • Oxidation and reduction reactions
  • Rearrangement reactions
44
Q

What is oxidation?

A

Oxidation is the addition of O2 and removal of H or electrons.

45
Q

What is reduction?

A

Reduction is the addition of H or electrons and removal of O

46
Q

What does primary alcohol oxidises to and what does a secondary alcohol oxidises to?

A

Primary alcohol oxidizes to aldehyde oxidizes to carboxylic acid oxidizes to acid chloride.
Secondary alcohol oxides to ketone

47
Q

What does acid chloride reduce to, what does ketone reduce to and what does alkyne reduce to?

A
  • Acid chloride reduces to carboxylic acid reduces to aldehyde reduces to primary alcohol
  • Ketone reduces to secondary alcohol
  • Alkyne reduces to alkene reduces to alkane
48
Q

What are electrophile?

A

Molecule/atom which accepts electrons to form a new bond, is the electrophile (electron-loving)

49
Q

What is a nucleophile?

A

Molecule/atom which donates electrons is the nucleophile (nucleus-loving)

50
Q

How does amides from?

A
  • Most used reaction in synthesis and biology is the reaction of a n amine with an acid to form an amide, in a condensation process where a molecule of water is formed.
  • Reactions require activation for acid to react with amine.
51
Q

What is ester hydrolysis important for?

A

Important as used for drug deliver.

52
Q

How do you overcome a drug with a physiochemical properties?

A
  • One way to overcome a drug with a poor physiochemical properties is the formation of a prodrug (a biologically inactive compound which can be metabolized in the body to produce a drug.)
53
Q

What is ester used for?

A
  • Ester used to mask acid which have poor physiochemical properties.
54
Q

Where is ester hydrolysed and how is ester hydrolysed?

A

Ester hydrolysed at the site of action liberating the active drug.
Chemically ester hydrolysis is very slow even in boiling water and requires accelerating, can be done through use of acids, bases or enzymes. (e.g bases such as NaOH)

55
Q

What is deprotonation?

A

Deprotonation = Loss of H+

56
Q

What is protonation?

A

Protonation = gain of H+

IDM (8 decks)

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