Chemistry Flashcards

(426 cards)

1
Q

How many elements are in the period table?

A

118

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2
Q

Who first created the periodic table and when?

A

Dmitri Mendeleev in 1869

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3
Q

How did Mandeleev arrange the periodic table?

A

In order of increasing atomic mass and similar properties. He left gaps for the undiscovered elements.

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4
Q

Each horizontal row in the periodic table is called?

A

A period.

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5
Q

Each vertical column in the period table is called?

A

A group.

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6
Q

Elements in the same group have?

A

Similar properties and the same number of valence electrons

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7
Q

Name of group group 1?

A

Alkali metals

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8
Q

Name of group 2?

A

Alkaline earth metals

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9
Q

Name of group 7?

A

Halogens

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10
Q

Name of group 8?

A

Noble gases

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11
Q

Name of elements in the middle block?

A

Transition metals

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12
Q

Elements of group 1?

A

Lithium, Sodium, Potassium, Rubidium, Cesium and Francium

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13
Q

Elements of group 2?

A

Beryllium, Magnesium, Calcium, Strontium, Barium, Radium

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14
Q

Elements of group 7?

A

Fluorine, Chlorine, Bromine, Iodine and Astatine

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15
Q

Elements of group 8?

A

Helium, Neon, Argon, Krypton, Xenon and Radon

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16
Q

Properties of alkali metals?

A

Soft, shiny metals
Good conductors of heat and electricity
Relatively low melting points
React vigorously with water
Form white products when combined with oxygen
Become more reactive moving down the group

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17
Q

Properties of alkaline earth metals?

A

Similar properties to alkali metals but slightly less reactive

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18
Q

Properties of the halogens?

A

Non-metals (apart from astatine a metalloid)
Highly reactive
Become less reactive going down the group
Can displace other less reactive halogens
Chlorine and fluorine are gases
Bromine is a liquid
Iodine is a solid

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19
Q

Properties of noble gases?

A

Unreactive as they have a full outer shell of electrons

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20
Q

Which side of the periodic table are metals found?

A

Left

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21
Q

Which side of the period table are non-metals found?

A

Right

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22
Q

Typical properties of metals?

A

Shiny solids (Mercury is the only metal that is liquid at room temperature)
They are ductile and malleable
High melting points
Good conductors of heat and electricity

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23
Q

Typical properties of non-metals?

A

Dull
Brittle
Not malleable or ductile
Poor conductors
Low melting points

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24
Q

What is a metalloid?

A

Have some properties similar to metals and some similar to non-metals
They are semiconductors as they can be modified to be conductors and insulators

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25
Around how many elements are essential in the human body?
20
26
Atom definition?
Smallest part of an elements which retains the characteristics of that element.
27
When did the idea of atoms become a scientific theory?
1808
28
Dalton’s atomic theory?
1) all matter is made up of atoms 2) all atoms of an element are similar to each other 3) atoms of different elements can combine to form compounds 4) atoms cannot be created or destroyed in chemical reactions
29
What kind of microscope can be used to see atoms?
Scanning tunnelling microscope
30
Who discovered the electron and when?
Thomson in 1897
31
How was the electron discover?
Thomson applied electricity to a glass tube producing cathode rays. The rays were attracted to a positively charged electrode meaning the rays must be negatively charged.
32
Who proposed the plum pudding model?
Thomson
33
Explain the plum pudding model?
A random distribution of electrons within a positive cloud.
34
Who disproved the plum pudding model and when?
Rutherford 1911
35
How did Rutherford discover the nucleus?
By aiming positively charged particles at a thin sheet of gold. Results showed most carried on straight but occasionally some were deflected meaning atoms must have a small positive centre (nucleus)
36
Mass and charge of an electron?
1/2000 -1
37
Mass and charge of a proton
1 +1
38
Mass and charge of a neutron?
1 0
39
Atomic mass unit (AMU) definition?
One-twelfth of the mass of carbon 12
40
What is the atomic number?
The number of protons (also number of electrons in a neutral atom)
41
What is the mass number?
The number of protons and neutrons
42
What is an isotope?
An atom of the same element which has a different amount of neutrons
43
Relative atomic mass (Ar) definition?
The weighted mean mass of an atom of an element compared to 1/12th of the mass of an atom of carbon-12 (1 amu)
44
Definition of relative isotopic mass?
The mass of an atom of an isotope compared to 1/12th of the mass of an atom of carbon-12
45
Definition of relative molecular mass (Mr)?
It is the mean mass of a molecule compared to 1/12th of the mass of an atom of carbon-12
46
What does a mass spectrometer determine?
Percentage abundance and isotopic mass of each isotope
47
What is needed to calculate relative atomic mass (Ar)?
Percentage abundance and isotopic mass of each isotope E.g. Mg-24 at 79% Mg-25 at 10% and Mg-26 at 11% (24x79)+(25x10)+(26x11) ———————————— 100
48
How to work out Relative molecular mass (Mr)?
Add together all the relative atomic masses of the atoms in the molecule
49
What is an ion?
An electricity charged atom
50
What is a negative ion?
Anion
51
What is a positive ion?
Cation
52
Metals form ......... ions?
Positive (cations)
53
Non-Metals form ......... ions?
Negative (anions)
54
Metals ...... electrons
Lose
55
Non-metals......electrons
Gain
56
Sulfate
SO4 (2-)
57
Sulfite
SO3 (2-)
58
Thiosulfate
S2O3 (2-)
59
Hydrogen sulfate
HSO4 (-)
60
Hydrogen carbonate
HCO3 (-)
61
Carbonate
CO3 (2-)
62
Nitrate
NO3 (-)
63
Nitrite
NO2 (-)
64
Phosphate
PO4 (3-)
65
Chlorate
ClO3 (-)
66
Hydroxide
HO (-)
67
Dichromate
Cr2O7 (2-)
68
Chromate
CrO4 (2-)
69
Permangenate
Mn04 (-)
70
Ammonium
NH4 (+)
71
Zinc ion
Zn2 (+)
72
Silver ion
Ag (+)
73
Copper (II) ion
Cu2 (+)
74
Iron (II) ion
Fe2 (+)
75
Iron (III) ion
Fe3 (+)
76
Name the diatomic molecules
Iodine, bromine, chlorine, fluorine, oxygen, nitrogen and hydrogen
77
What is an energy level?
Each electron shell
78
What is an orbital?
An electron sub-shell
79
How many electrons can each orbital hold?
2
80
What are the different types of orbitals?
S- P- D- F-
81
What shape are s-orbitals?
Sphere
82
What shape are p-orbitals?
Dumbell shaped
83
How many s-orbitals does each shell have?
1
84
How many p-orbitals does each shell have?
3
85
How many d-orbitals are in each shell?
5 (only from shell 3 onwards)
86
How many f-orbitals does each shell have?
7 (from shell 4 onwards)
87
How many electrons can energy levels 1-4 contain?
2,8,18,32
88
Why do electrons in an orbital spin in opposite directions?
To minimise the repulsion between electrons
89
Ionisation energy definition?
The energy needed to remove one electron from each atom in one mole of gaseous atoms to form one mole of gaseous 1+ ions
90
What is ionisation energy measured in?
KJ per mole
91
How to work out empirical formula?
Divide masses by relative atomic mass (to find moles) Divide each number by the smallest one These numbers show the ratio required
92
What is a mole?
The amount of substance that contains 6.022x10(23) particles
93
What is Avogadro’s number?
6.022x10(23) (the same as the number of particles in each mole of carbon 12)
94
One mole of any substance is equal to?
It’s relative atomic mass turned into grams
95
What are moles measured in?
g/mol
96
How to work out number of moles?
Mass divide by formula mass
97
How to work out mass?
Moles multiplied by formula mass
98
How to work out formula mass?
Mass divided by moles
99
What is percentage composition?
The percentage by mass of each element present in a compound
100
How to work out percentage composition?
Multiple relative atomic mass by number of atoms Divide by molecular mass of compound Multiple by 100
101
What is molecular formula?
The actual number of atoms of each element in a molecule.
102
What is empirical formula?
The simplest whole number ratio of atoms or ions of each element in a compound
103
How to work out molecular formula?
Find empirical formula Divide actual mass by empirical formula mass
104
What is a solution?
A mixture of solute and solvent particles
105
Concentration definition?
Amount of solute in a given amount of solution
106
Molarity meaning?
An expression of concentration 1M = 1 mole of substance in 1dm(3) of its solution
107
How to work out concentration?
Number of moles divided by volume
108
Molar gas volume definition?
The volume per mole of gas molecules at a stated temperature and pressure
109
What is the volume of one mole of any gas at room temperature and pressure?
24dm(3)
110
How to convert cm(3) to dm(3)?
Divide by 1000
111
How to calculate the volume of gas (dm3)?
Number of moles of gas x 24
112
How to calculate the number of moles of a gas?
Volume of gas (dm3) —————————— 24
113
Percentage yield definition?
Shows how much product is obtained compared to the maximum possible mass
114
Atom economy definition?
The percentage of atoms in reactants that form the desired product
115
Theoretical yield meaning?
The maximum amount of product that could be formed
116
Why is it difficult to achieve theoretical yield?
Reaction may not have gone to completion Other side reactions may have taken place Purification of the product may result in some loss of product Some product may be left behind in apparatus Raw materials may not be pure
117
How to calculate percentage yield?
1) find moles of product 2) find ratio of moles of product to reactant Actual yield —————— x 100 Theoretical yield
118
Limiting reagent meaning?
Any reactant that is not in excess. Meaning the reacting will stop as soon as this is used up.
119
How to work out the limiting reagent?
Used the balanced equation to see which reactant is used up quicker
120
How to work out atom economy?
The mass of useful product ————————————x 100 Total mass of all products
121
Why is it useful to maximise percentage yield and atom economy?
Reduce energy use Reduce costs Conserve raw materials Reduce waste Reduce pollution
122
What is a titration used for?
To calculate the concentration of an unknown
123
How to work out concentration from a titration?
1) calculate the volume, concentration and moles of the known substance 2) use the balance equation to work out mole ratio 3) use the mole ratio to work out the moles of the unknown 4) use the moles and volume of the unknown to finally workout the concentration
124
What is volumetic analysis?
Finding the concentration of a solution by measuring the volume of a solution that will react with a known volume of standard solution
125
What is the equation to work out a dilution?
Initial conc. x initial vol. = new conc. x new vol This is then rearranged as required
126
Saturated solution definition?
A chemical solution containing the maximum concentration of a solute dissolved in the solvent at a particular temperature. No more solute will dissolve.
127
Supersaturated solution meaning?
A solution that contains a higher that saturation concentration of solute. Any slight disturbance causes crystallisation of excess solute
128
Solubility definition?
A chemical property referring to the ability for a given substance to dissolve in a solvent
129
Precipitate meaning?
Insoluble solid that forms during a chemical reaction and separates out in solution
130
How to test if chloride ions are present?
First silver nitrate: white precipitate Then dilute ammonia: precipitate disappears Then concentrated ammonia: N/A
131
How to test if bromide ions are present?
First silver nitrate: cream precipitate Then dilute ammonia: precipitate remains Then concentrated ammonia: precipitate disappears
132
How to test if iodide ions present?
First silver nitrate: yellow precipitate Then dilute ammonia: precipitate remains Then concentrated ammonia: precipitate remains
133
How to test for carbonate ions?
Add dilute HCl acid to sample If effervescence observed carbonate is likely Transfer gas to limewater, if cloudy CO2 is present
134
How to test for sulfate ions?
Add barium chloride to sample. If present white barium sulfate precipitate will form
135
Types of chemical bonds?
Ionic Covalent Dative/co-ordinate covalent Metallic
136
Types of physical bonds?
Van der Waals’ forces Dipole-dipole interaction Hydrogen bonds
137
What is an ionic bond?
An electrostatic force of attraction between positive and negative ions, usually between a metal and a non-metal
138
Structure of ionic compounds?
Each ion attracts oppositely charged ions in all directions. Resulting in a giant ionic lattice structure containing billions of atoms
139
Properties of ionic bonds in regards to melting/boiling?
Most are solids at room temperature as there is insufficient energy to overcome the strong electrostatic forces of attraction so most have high melting and boiling points the greater the ionic charge the higher the point The larger the ion the lower the point as weaker bonds due to being spread over a large surface
140
Properties of ionic bonds in regards to solubility?
Most soluble in polar solvents such as water. Ionic lattice is broken down and solvent molecules surround the ions. The stronger the lattice the less soluble to compound.
141
Properties of ionic bonds in regards to electrical conductivity?
Can conduct electricity it only if charged ions can move. So solids cannot but molten/ dissolved compounds can.
142
What is a covalent bond?
Strong electrostatic attraction between a shared pair of electrons and the nuclei of the bonded atoms. Occurs in non metals elements, non metal compounds and poly atomic ions
143
What is a simple covalent molecule?
A few atoms held together by covalent bonds
144
What are giant covalent structures?
Contain many atoms, each joined to adjacent atoms by covalent bonds. Usually arranged into giant regular lattices
145
Properties of simple covalent structure in regards to temperature?
Low melting and boiling points as less energy needed to break weak intermolecular forces (not strong covalent bond)
146
Properties of simple covalent structure in regards to solubility?
They can either be polar or non-polar. Polar molecules dissolve in polar solvents. Non-polar molecules dissolve in non-polar solvents
147
Properties of simple covalent structure in regards to electrical conductivity?
Do not conduct electricity as they do not have any free electrons or an overall electric charge
148
What is an allotrope?
A different form of the same element in the same state. E.g. graphite and diamond
149
Properties of giant covalent structure in regards to temperature?
High melting and boiling points due to presence of strong covalent bonds in the structures
150
Properties of giant covalent structure in regards to electrical conductivity?
Depends if there are any delocalised electrons. E.g. graphite will conduct but diamond will not
151
Properties of giant covalent structure in regards to solubility?
They are not soluble as covalent bonds in the lattices are too strong to be broken
152
What is metallic bonding?
Electrostatic interaction between positive metal ions and delocalised electrons. The atoms are ionised and these ions occupy fixed positions in the lattice. Outer shell electrons are delocalised and shared between all atoms within the structure
153
Properties of metallic bonds in regards to electrical conductivity?
Most conduct electricity in solid and liquid state. The delocalised electrons can move through the structure carrying a charge
154
Properties of metallic bonding in regards to temperature?
Most metals have high melting and boiling points. Depends upon the strength of metallic bonds within the structure. High temperatures are needed to overcome strong electrostatic attraction between the cations and electrons. The higher the ionic charge of the metal the higher the melting point
155
Properties of metallic bonds in regards to solubility?
Metals do not dissolve. Any interaction between polar solvents and changed in metallic lattice would lead to reaction rather than dissolving
156
Properties of metallic bonds in regards to malleability/ductile?
Metals can be hammered and pressed into shape as atoms can roll over each other into new positions without the bonds breaking Metals can be drawn out into a wire again due to atoms rolling over each other
157
What is an alloy?
Mixtures containing metals. Not a compound as there can be different ratios of metals. They can modify a metals properties e.g. ions may be different sizes to stop layers moving past each other making it harder
158
What is a dative/coordinate bond?
Very similar to a covalent bond apart from both electrons involved in the bond are from the same atom.
159
Intramolecular forces definition?
The forces that hold atoms together within a molecule
160
Intermolecular forces definition?
Forces that exist between molecules
161
Three categories of of intermolecular bonding?
Induced dipole-dipole interactions (London/ Van der Waals) Permanent dipole/dipole interactions Hydrogen bonding
162
Which type of force is weaker?
Intermolecular
163
What is electronegativity?
A measure of the tendency of an atom to attract a bonding pair of electrons in a covalent bond. The greater the electronegativity the greater the attraction.
164
What did Linus Pauling invent in 1932?
The Pauling scale to measure electronegativity of atoms
165
Electronegativity........ across a period
Increases
166
How does atomic radius affect electronegativity?
As the radius increases the bonding pair of electrons becomes further from the nucleus. They are therefore less attracted to the nucleus. So the greater the radius the lower the electronegativity.
167
How does the number of unshielded protons affect electronegativity?
Full energy levels of electrons shield the electrons in the bond from the increased attraction of the greater nuclear charge, reducing electronegativity
168
Electronegativity ...... down a group?
Decreases
169
What a non-polar bonds?
The electronegativity in both atoms of the covalent bond is identical so the electrons are equally attracted to them both. This cause symmetrical distribution of electron density around the two atoms.
170
What is a polar bond?
When a covalent bond is formed by atoms with different electronegativities.
171
Dipoles meaning?
When there is asymmetrical distribution of electron density because one atom attracts the electrons more strongly this created an imbalance in the charges in the bond.
172
What symbol is used to show charges between bonds?
Delta positive and delta negative
173
Polar bonds have a more ........ character?
Ionic
174
Non-polar bonds have a more ......... character?
Covalent
175
What is a non-polar molecule?
If the polar bonds are arranged symmetrically, the partial charges cancel each other
176
What is a polar molecule?
If polar bond are asymmetrically arranged, the partial charges do not cancel each other out
177
What are van der Waals forces?
Resulting weak forces of attraction between the small charges (temporary dipoles)
178
How does atomic radius affect van der Waals forces?
As the radius increases the electrons are less attracted to the nucleus so temporary dipoles are easier to induce
179
How do the points of contact between molecules affect van der Waals forces?
The more points of contact between the molecules the stronger the van der Waals forces
180
What a permanent dipole-dipole forces?
If molecules contain bonds with a permanent dipole the molecules may align so there is electrostatic attraction between the opposite charges on neighbouring molecules
181
What is a hydrogen bond?
A special type of permanent dipole-dipole bond interaction found between molecules containing: An electronegative atom with a lone pair of electrons e.g. oxygen, nitrogen, fluorine A hydrogen atom attached to the electronegative atom. The hydrogen bond acts between the hydrogen atom in one molecule and the lone pair of electrons in an electronegative atom of another molecule
182
Strength of intermolecular forces from highest to lowest?
Hydrogen Permanent dipole/dipole Van der Waals
183
Why is solid water less dense that liquid water?
Hydrogen bonds hold water molecules further apart in an open lattice structure when solid. So the water molecules in ice are further apart than in water
184
What influences the shape of a molecule?
The total number of electron pairs around the central atom. Lone pairs repel more than bonding pairs.
185
What is bond length?
The distance between the nuclei of two bonded atoms
186
What is bond angle?
The angle between two covalent bonds
187
Basic principles of electron pair repulsion theory?
The electron pairs around the central atom determine the shape of the molecule or ion The electrons pairs repel electrons each other so they are arranged as far apart as possible The arrangement of electron pairs minimise repulsion and therefore holds the bonded atoms in a definite shape Different number of electron pairs result in different shapes
188
What is a tetrahedral shape molecule?
Four bonded pairs repel each other as far as possible Bond angle of 109.5 e.g. methane
189
What is a pyramidal shape molecule?
Contains 3 bonded pairs and one lone pair of electrons. Since the lone pairs repel more strongly than bonded pairs this means the bonded angles are closer together decreasing the bond angle Bond angle of 107 e.g. ammonia
190
What is a non-linear molecule?
Two bonded pairs and two lone pairs. The lone pairs repel more strongly creating the V-shape Bond angle of 104.5 E.g. water
191
What is a linear shaped molecule?
Molecules that contain 2 bonding regions but not lone pairs Bond angle 180 E.g. CO2
192
What is a triagonal planar shape molecule?
Contains 3 bonded pairs and no lone pairs. Bond angles of 120 E.g. boron trifluoride
193
What is an octahedral shape molecule?
6 bonded pairs and no lone pairs Bond angle of 90 E.g. SF6
194
How to predict molecular shape and angles?
1) work out number of valance electrons of central atom 2) take into account any charges for ions 3) work out the number of covalent bonds made by the central atom 4) work out amount of electron pairs 5) determine the shape
195
What is a triagonal bipyramidal shape molecule?
5 bonded pairs and no lone pairs 2 x 90 3 x 120
196
What is endothermic?
Heat taken in, in a chemical reaction. The products have more energy than the reactants.
197
What is exothermic?
Heat given out, in a chemical reaction. The products have less energy than the reactants.
198
What is activation energy?
Energy needed to start a reaction. Activation energy used to break bonds so reaction can take place and new bonds can form.
199
What is bond enthalpy?
The energy it takes to break one mole of a specific bond type in gas form.
200
How to calculate energy change?
Draw out bonds Use average bond enthalpy table Sum of bond enthalpies of bonds broken - sum of bond enthalpies of bonds made. - figure shows exothermic + figures shows endothermic
201
What is calorimetry?
Doing an experiment in set conditions so you can measure temperature change. Allows you to measure enthalpy change directly. Gives true value rather than approximate. Mass of surroundings x specific heat capacity of surrounding x change in temperature of surroundings. Then usually scale up to one mole. Surroundings usually = water
202
What is specific heat capacity?
The energy required to raise the temperature of 1g of a substance by 1C. Units: JK-1g-1 Specific heat capacity of water: 4.18
203
What is enthalpy of reaction?
Overall energy change at constant pressure, if the conditions are standard conditions we call it the standard enthalpy of reaction
204
What are standard conditions?
Pressure of 100kPa Temperature of 298K (25°C) Concentration of 1M, for reactions with aqueous solutions The standard state is the physical state of a substance under standard conditions. E.g. H20 is liquid
205
Standard enthalpy change of reaction definition?
The enthalpy change that accompanies a reaction in the molar quantities expressed in a chemical equation under standard conditions, all reactants and products being in their standard states.
206
Standard enthalpy change of combustion definition?
The enthalpy change that takes place when one mole of a substance reacts completely with oxygen under standard conditions, all reactants and products being in their standard states. Since it is only one mole there may be fractions of other substances in the equation.
207
Standard enthalpy of formation definition?
The enthalpy change that takes place when one mole of a compound is formed from its constituent elements in their standard states under standard conditions.
208
What is Hess’ law?
If a reaction can take place by more than one route and the initial and final concentrations are the same, the total enthalpy change is the same.
209
How to use an enthalpy cycle?
Add if arrow going correct way Subtract if arrow going wrong way Combustion reactants-products Formation products-reactants
210
What is entropy?
A measure of disorder Solids lower Gases higher
211
Reaction rate formula?
Change in concentration (mol dm-3) —————————————— Time for change to occur (seconds) For the average time For more specific use a graph and use a tangent to work out the gradient
212
What can increase rate of reaction?
Increase temperature Increase reactant concentration Increase reactant pressure Increase surface area e.g. use a powder Adding a catalyst
213
Collision theory?
1) particles have to collide 2) have collision energy equal to or greater than the reactions activation energy 3) collide with proper orientation
214
How does a catalyst affect kinetics?
Increases the rate of reaction without being consumed. The reaction follows a different reaction route, usually with a lower activation energy.
215
Types of catalyst?
Homogeneous catalyst- reactant and catalyst in same states Heterogeneous catalysts- reactant and catalyst in different states
216
Maxwell Boltzmann curve?
Total area under the curve= total number of molecules in the system Area under the curve and to the right of activation energy= number of molecules with sufficient energetic to react
217
Main characteristics of maxwell Boltzmann distribution?
No particles have 0 energy Most particles have intermediate energy A few particles have high energy The average energy is not the same as the most probable energy
218
What is equilibrium?
When reversible reactions reach a balance point, where the amount of reactants and the amount of products formed remains constants.
219
What is dynamic equilibrium?
The forward and backwards reactions continue at equal rates so the concentrations of reactants and products do not change. On a molecular scale there is constant change, but on the macroscopic scale nothing appears to be happening. Required conditions: 1) must be a reversible reaction 2) must be in a closed container
220
What is La Chatelier’s principle?
If a dynamic equilibrium is disturbed by changing the conditions, the position of equilibrium moves to counteract the change.
221
Factors that affect the position of equilibrium?
1) pressure 2) concentration 3) temperature
222
La chatelier’s principle with a change in concentration
If you increase the concentration of the reactants, the equilibrium will shift to the right If you decreases the concentration of the reactants, the equilibrium will shift to the left If a product is removed the equilibrium would shift to the right. If the product was continually removed the reaction would eventually turn into an irreversible reaction.
223
La chatelier’s principle with a change in pressure
Only applies to reactions involving gases If pressure is increased the equilibrium will move in the direction on the least molecules to try to reduce the pressure. If pressure is decrease the equilibrium will move in the direction on the most molecules to try to increase the pressure. If there are the same number of molecules on each side, changing the pressure would have no effect on the position of equilibrium
224
La chatelier’s principle with a change in temperature
Depends if the forward reaction is exothermic to endothermic If temperature is increased the equilibrium will try to cool down. The equilibrium will move towards the endothermic reaction. If temperature is decreased the equilibrium will try to heat up. The equilibrium will move towards the exothermic reaction.
225
Catalysts and equilibrium
They have no influence on the position of equilibrium but help it to be reached quicker
226
Industry and la Chateliers principle
Important as can a determine conditions for highest yield but need to consider: Low temperature and pressure means slow rate of reaction High temperature and pressure means expensive to run and build suitable equipment So most use a compromise set of conditions
227
What is the equilibrium constant?
Kc Different for every reaction The size of Kc shows how far a chemical reaction has gone. Indicates the position of equilibrium
228
What does Kc value tell us?
If \>1 the reaction is product favoured so equilibrium lies to the right If \<1 the reaction is reactant favoured so equilibrium lies to the right When Kc is 10^10 they are regarded as gone to completion, so no longer reversible When Kc is 10^-10 the reaction is regarded as not taking place
229
How to work out Kc?
aA + bB cC + dD Kc = [C]^c [D]^d ——————- [A]^a [B]^b So equilibrium concentration of products divided by reactants, raised to the power of their stoichiometry
230
How to work out Kc questions
Find out the initial amounts, changes and therefore equilibrium moles Find concentrations, so moles/volume Use Kc expression
231
What is organic chemistry?
Concerned with compounds of carbon
232
What do organic compounds contain?
Carbon, hydrogen and sometimes oxygen and other non-metallic elements
233
What order are formulas for organic compounds written?
Carbon Hydrogen Then any others
234
Features of carbon?
Can form an infinite number of compounds Can make up to four covalent bonds (single, double or triple) Can form covalently linked C-C chains of unlimited length Forming a variety of branches, linear and cyclic compounds
235
Name of linear hydrocarbons?
Aliphatic
236
Name of branched hydrocarbons?
Alicyclic
237
Name of ring shape hydrocarbons?
Aromatic
238
How can carbon skeletons vary?
Length Branching Double bind positions (if present) Presence of rings
239
Homologous series definition?
A group of organic chemical compounds, that have similar structure and properties, the structure only differs by the number of CH2 units in the main carbon chain
240
Arrangement of bonds carbon can form?
4 single bonds 2 double bonds 2 single bonds and 1 double bond 1 single bond and 1 triple bond
241
What is the alkane formula?
C(n)H(2n+2)
242
Alkanes end in the suffix of?
Ane (methane, ethane, propane)
243
Alkane structure?
Hydrocarbons Only have single C-C bonds Saturated (have maximum number of hydrogens)
244
How are unbranched alkanes named?
The pre-fix of the number of carbons in chains followed by ‘ane’
245
How are branched alkanes named?
1) identify the longest carbon chain in any direction 2) number the carbon chain (make sure the branched group has the lowest number possible) 3) find the name of of longest chain e.g. octane 4) find the name of the branched group e.g. meth and add ‘yl’ 5) find the number of the carbon the branch group is on 6) e.g. 2-methyloctane 7) write in alphabetical order if more than one branch group
246
Number of carbon chains and names for alkanes?
1) meth 2) eth 3) prop 4) but 5) pent 6) hex 7) hept 8) oct 9) non 10) dec
247
What is the name of a branch off of a alkane?
Alkyl group
248
What is a halogenoalkane?
Where one or more hydrogen from an alkane is replaced by a halogen Name added to alkane with number of branch
249
What state are the first 4 alkanes at room temperature?
Gas
250
What state are alkanes 5-8 at room temperature?
Liquid
251
Alkane properties in terms of boiling point?
The longer the carbon chain the higher the boiling point as the chain increases so does the number of electrons in the molecules so the van der Waals forces are stronger Straight alkanes have higher boiling points that branches alkanes as the molecules can lie closer together
252
Alkene structure?
End in ‘ene’ Have at least one C-C double bond Unsaturated (doesn’t have maximum number of hydrogen atoms)
253
What is the alkene formula?
H(n)C(2n)
254
Alkyne structure?
End in ‘yne’ Contain at least one C-C triple bond Unsaturated
255
Naming alkenes/alkynes
1) The longest carbon chain must contain the double/triple bond 2) number carbon chain from the end closest to double/triple bond 3) add number to name of the carbon the double bond is on 4) add any groups e.g. methyl
256
How to test if alkane or alkene?
Use bromine water Becomes colourless if alkene as bromine reacts with C-C double bond Stays red/brown if alkane as no double bond to react with
257
What is hydrogenation?
A reaction in which hydrogen atoms add to each of the carbon atoms in a double bond of an alkene turning it into an alkane A metal catalyst is used
258
What is a cycloalkane?
A ring of carbon atoms with two hydrogen atoms attached to each carbon Formula of C(n)H(2n) They are saturated Add cyclo to the name
259
What is an arene?
Group of aromatic hydrocarbons with a molecular structure containing one or more flat sets of six carbon atoms. Each carbon forms a single covalent bond to the carbons either side and to one hydrogen atom. The final unpaired electron on each carbon is located in the P-orbital that sticks out above and below the plane of the ring. This forms a ring of delocalised electrons. Unsaturated cyclic hydrocarbons Benzene is an example
260
Structure of benzene?
Molecular formula of C6H6 Ring structure Groups can be added off of benzene
261
What is the displayed formula?
Shows the arrangement of atoms and the bonds
262
What are isomers?
Compounds with the same molecular formula but the atoms are arranged differently which can lead to differences in physical and chemical properties
263
Types of structural isomers?
Chain length isomers Position isomers Functional group isomers
264
Types of stereoisomers?
Geometric isomers Optical isomers
265
What are chain length isomers?
Carbon atoms in skeleton arranged differently
266
What are positional isomers?
Have the same functional groups but attached to different points of the main chain
267
What are functional group isomers?
Have different functional groups E.g. alkane, alkene, alcohol, ether
268
What is a stereoisomer?
Have the same structural formula but different in the arrangement of bonds
269
What is cis-trans isomerism?
Differ in the arrangement of the groups attached to the carbons in double bonds
270
What are sigma bonds?
End to end overlap of atomic orbitals All single bonds
271
What are Pi bonds?
When the lobe of one atomic orbital overlaps another Double bonds have a Pi bond as wells as a sigma bond
272
What is the difference between cis and trans isomers?
If the atoms other than hydrogen are all on the same side of the chain they are cis isomers If the atoms other than hydrogen are different sides of the chain they are trans isomers
273
Limitation of cis-trans isomerism?
Hard to figure out which side of which if lots of hydrogens have been substituted for different groups E.g. one side may have carbon and chlorine and the other fluorine and bromine
274
What is E-Z isomerism?
Used to identify stereoisomers that cannot be defined at cis or trans Isomers identified as either E or Z The higher the atomic number the higher the priority E corresponds to trans form (opposite sides) Z corresponds to cis form (same sides)
275
What is optical isomerism?
Have the same molecular and structural formula but cannot be superimposed as they are mirror images Can occur when an asymmetric carbon (bonded to four different groups) is present so it forms a chiral centre of the molecule
276
What is a chiral centre?
When a carbon atoms is bonded to four different groups
277
How to tell the type of optical isomer?
Can rotate the plane of polarised light. Clockwise - positive enantiomer (D form) Anti-clockwise- negative enantiomer (L form) No effect- racemic/racemate
278
What is R and S configuration?
Assign priority to all groups from chiral centre by atomic number View molecule so lowest priority is away from observer Arrow is drawn around in order of priority groups If arrow is clockwise it is R form If arrow is anti-clockwise it is S form
279
How are halogenoalkanes made?
Free radical substitution
280
How are halogenoalkenes made?
Electrophilic addition
281
What are the three key steps of free radical substitution?
1) initiation 2) propagation 3) termination
282
What is initiation in free radical substitution?
UV light absorbed by halogen molecule to provide energy to break the bond. One electron goes to each halogen and forms two free radicals (homolytic fission)
283
What is homoloytic fission?
Single bond breaks, one electron to each molecule. Shown by a curly half arrow head. Forms two products that are the same
284
What is heterolytic fission?
Breaking of bonds. One atoms gains both electrons. So atom is now negatively charged and other is positively charged. Two different products
285
What is a free radical?
A highly reactive species with a single unpaired electron. Electron is represented by a dot.
286
What is propagation in free radical substitution?
A halogen radical reacts with a methane molecule. This removed hydrogen from the methane and forms a methyl radical and hydrogen chloride. The methyl radical can then bond with a halogen molecule forming another halogen radical and halogenmethane. During this process the total number of radicals remains the same.
287
What is termination in free radical substitution?
Total number of free radicals decreases. Free radicals can join together to create stable molecules. Methyl to halogen Halogen to halogen Methyl to methyl
288
Why is the process of synthesising halogenoalkanes by reacting alkanes with a halogen not cost effective?
Hard to separate the mixture of products formed
289
What are chlorofluorocarbons?
Halogenoalkane molecules where all the hydrogen atoms have been replaced by fluorine or chlorine.
290
Why are chlorofluorocarbons bad?
Destroy the ozone layer (O3) due to free radical substitution
291
How are halogenoalkanes formed from alkanes?
Electrophilic addition. As the double bond is an area of high negative charge making it very reactive.UV light is not needed.
292
What is an electrophile?
Electron pair acceptor. They accept a pair of electrons to form a covalent bond. They are electron deficient. Represented as E+.
293
What is a nucleophile?
Electron pair donator. They donate a pair of electrons to form a covalent bond. They can be represented by Nu:
294
What is the electrophilic addition mechanism?
The double bond in the alkene is electron dense (negatively charged). The electrophile is attracted to this. The electrophile breaks down and undergoes heterolytic fission so both the electrons go to the atom not attaching to the double bond. Finally the atom that accepted the electrons bonds with the other carbon to form a dative covalent bond.
295
What are alcohols?
Homologous series of organic compounds with the general formula CnH2n+1OH Names end in ol Functional group is OH
296
How to name alcohols?
Name of length of carbon chain with suffix -ol If there are 3 or more carbons positional isomerism can be displayed The carbon number the OH is attached to is written before -ol
297
Properties of alcohols?
Much higher boiling point than alkanes Boiling point increases as carbon chain length increases Most are liquid at room temperature
298
Explaining properties of alcohols?
The electronegative oxygen atom in the hydroxyl group means alcohols are polar so can take part in hydrogen bonding meaning the boiling point will be higher than that of an alkane Hydrogen bonding also means alcohols can mix with water
299
How can alcohols be produced?
Hydration of an alkene add water to alkene in form of steam with a phosphoric acid catalyst. Temperature must be 570K and pressure 60-70 atm Fermentation Glucose + yeast —\> ethanol + carbon dioxide Anaerobic conditions Temperature 25-35c Yeast dies when ethanol concentration reaches around 15% Slow process
300
Advantages of fermentation?
Renewable resources used Less energy used
301
Advantages of hydration?
High yield of ethanol Atom economy of 100% Fast reaction Can be done continuously
302
Types of alcohols?
Primary: have one R group attached to the carbon to which the OH group is attached Secondary: have two R groups attached to the carbon to which the OH group is attached Tertiary: have two R groups attached to the carbon to which the OH group is attached
303
Function group of aldehyde and ketones?
Carbonyl group C=O
304
Formula of aldehydes and ketones?
CnH2nO
305
Differences between aldehydes and ketones?
Carbonyl group at the end is an aldehyde. So it has at least one hydrogen attached to it Carbonyl group in the middle is a ketone so has two carbons attached to it
306
How to name aldehydes?
Named using carbon chain length and then the suffix -al Carbons numbered starting with carbonyl group as 1
307
How to name ketones?
Using length of carbon chain and suffix -one Carbon number of carbonyl group placed before suffix
308
Reactivity of the carbonyl group?
Polar Positive charge on the carbon makes it open to attacked by nucleophiles Aldehydes and ketones can be reduced, forming alcohol Aldehydes can be oxidised to carboxylic acids
309
Properties of aldehydes and ketones?
Small ones are soluble in water due to hydrogen bonding between a lone pair on the oxygen of the carbonyl group and the hydrogen of water As size increases solubility decreases due to interference in hydrogen bonding by the hydrocarbon tails Have mid range boiling points as have van der Waals forces AND the polar carbonyl group means dipole-dipole interactions are present
310
Comparing boiling points of alkanes, ketones & aldehydes, alcohols and carboxylic acids?
Alkanes have the lowest as only van der Waals forces are present Aldehydes & ketones are higher as they also have dipole-dipole interactions as the carbonyl group is polar Alcohols are higher still as they also have hydrogen bonding Carboxylic acids are highest as they have more hydrogen bonds
311
How are aldehydes produced?
Primary alcohols can be oxidised by an oxidising agent such as an aqueous solution of acidified potassium dichromate which changes colour from orange to green. Water is also produced in the reaction.
312
How are ketones produced?
Secondary alcohols can be oxidised by an oxidising agent such as an aqueous solution of acidified potassium dichromate. Water is also produced
313
Why are tertiary alcohols resistant to oxidation?
The lack of hydrogen atoms on the carbon atom to which the hydroxyl group of attached
314
How to test whether aldehyde or ketone?
Tollens’ reagent: Sodium hydroxide + aqueous silver nitrate. This forms a brown precipitate of silver nitrate (Ag2O). Aqueous ammonia is added until precipitate dissolves and a solution of the silver amine [Ag(NH3)2]+ is formed. A silver colour is formed if aldehydes are present No colour change if ketone Benedict’s solution: An alkaline solution containing copper ions. When heated with an aldehyde the Cu2+ complex ion acts as an oxidising agent and the blue turns to red No colour change if ketone
315
Functional group of carboxylic acids?
Carboxyl group (COOH) attached to terminal carbon
316
How to name carboxylic acids?
Using length of carbon chain and suffix -oic acid
317
Reactivity of carboxylic acids?
Polar due to presence of two electronegative oxygen atoms and a partially charged carbon and hydrogen atom Can take part in: Neutralisation- carboxylic acid loses a proton to from a carboxylate salt Nucleophillic substitution- partially positive carbon is attacked by nucleophile resulting in substitution of OH group Esterification- reaction with an alcohol for form an ester
318
Properties of carboxylic acids?
Solubility depends on side. The smaller the compound the higher the solubility. Carboxylic acids are higher due to more hydrogen bonds present
319
How are carboxylic acids formed?
Primary alcohols are reacted with an excess of oxidised agent and refluxed. Primary alcohol—\>aldehyde —\>carboxylic acid Reflux position is the condenser tube vertical. The condenser tube is continuously surrounded by cold water. As aldehyde is produced it evaporates but the cold water then cools it back to a liquid so it can go back to undergo second oxidisation Reflux definition: the continuous evaporation and condensation of a volatile substance without loss of any product
320
Functional group of esters?
-COO- Carbon double bonded to one oxygen and single bonded to another oxygen
321
How is an ester formed?
Esterification: When alcohol is warmed with a carboxylic acid in the presence of an acid catalyst. A water molecule is removed Concentrated sulfuric acid is often used as the catalyst The O-H bond of alcohol is broken and water formed with the OH from the carboxylic acid group and the H in the alcohol group Carboxylic acid + alcohol -\> ester + water
322
Naming esters?
First part from the alcohol used with -yl e.g ethyl Second part from carboxylic acid used with -anoate e.g. ethanoate X-yl X-anoate
323
Hydrolysis of esters?
Chemical reaction using water to break down bonds of a substance Esters can be hydrolysed by refluxing with either an acid or alkali With an acid it reverses the ester back to an alcohol and carboxylic acid With an alkali it hydrolysed to an alcohol and sodium salt of the acid
324
What is an amine?
Nitrogen containing organic compounds derived from ammonia where one or more of the hydrogen atoms has been replaced by an alkyl or aryl group
325
Types of amines?
Primary: where one hydrogen from ammonia is substituted with carbon Secondary: where two hydrogens from ammonia are substituted Tertiary: where all three hydrogen atoms are substituted Quaternary: where four carbons are attached to the nitrogen, using ammonia’s lone pair of electrons
326
Naming amines?
Use the length of the carbon chain and use suffix -amine E.g. methylamine If other functional groups are present then the amino- prefix is used E.g. 2-aminoethanoic acid
327
Properties of amines?
Solubility: shorted chains are soluble in water as the lone pair of electrons in the nitrogen atom allows them to form hydrogen bonds with water molecules Larger amines are less soluble as the larger R groups interfere with hydrogen bonds Boiling points: primary amines have higher boiling points that alkanes as they can form hydrogen bonds . Secondary amines having slightly lower boiling points as the nitrogen forming the hydrogen bond is in the middle of the chain and this slightly reduces the strength of the dipole Tertiary amines have even lower boiling points
328
What is an amide?
Products of reactions between carboxylic acids and amines An amide and water is produced Contain functional group CONH Amino acids contain both amine and carboxylic acid functional groups. They can react together to form an amide link (peptide bond)
329
Common acids and their formulae?
Hydrochloric acid: HCL Nitric acid: HNO3 Ethanoic acid: CH3COOH Sulfuric acid: H2SO4
330
Arrhenius model of acids and bases?
Acids dissociate and release H+ ions in an aqueous solution Alkalis dissociate and release OH- ions in an aqueous solution
331
What is neutralisation?
An acid plus a base equals salt and water H+ + OH- ---\> H2O For example: NaOH + HCl ---\> NaCl + H2O
332
Bronsted-Lowry acid and base model?
Emphasises the role of the proton transfer An acid is a substance that can donate a proton A base is a substance that can accept a proton
333
What is the hydronium ion?
H3O+ The active ingredient in any acicid solution Usually shortened to H+
334
What is an conjugate acid-base pair?
It contains two species that the transfer of a proton can interconvert
335
Amphoteric meaning?
It can act as both an acid and a base Such as water
336
What do the terms monobasic, dibasic and tribasic refer to?
The total number of hydrogen ions in the acid that can be replaced per molecule
337
What is a strong acid?
They fully dissociated in water
338
What is a weak acid?
They only partially dissociate in water
339
What is a concentrated acid?
A high number of moles of acid in 1dm3 of solution
340
What is a weak acid?
A low number of moles of acid in 1dm3 of solution
341
How to calculate pH of a strong acid?
pH = -log10 [H+] The square brackets mean concentration in mol dm-3 of hydrogen ions If diprotic or triprotic, then multiple concentrations by two or three as they will contain more moles of hydrogen per molecule
342
How to calculate the hydrogen ion concentration from pH?
10^-pH Eg pH 8.75 is 10^-8.75 = 1.78 x 10^-9 mol dm^-3
343
The equilibrium constant of water?
Kw= [H+][OH-] Since the H and OH in water are equal, it can also be written as: Kw=[H+]^2
344
How does the pH of water change?
With temperature
345
Calculating pH from Kw?
Kw = [H+]^2 [H+] = square root of Kw Then calculate pH as normal, -log[H+]
346
Buffer definition?
An aqueous solution that resists change in pH upon the addition of acid or base
347
How to prepare a buffer?
Mix a large volume of weak acid/base with its conjugate base/acid
348
How does a buffer work?
When a strong base is added, the acid present in the buffer neutralises the hydroxide ions When a strong acid is added, the base present in the buffer neutralises the hydronium ions
349
Standard structure of steroids?
Three cyclohexane rings One cyclopentane ring 17 labelled carbons
350
Solubility of steroids?
Fat-soluble Derived from fatty acid biosynthesis have a hydrophobic core Some functional groups may impart polarity/ water solubility
351
What is the simplest steroid?
Gonane Cyclopentanoperhydrophenanthrene
352
How many chiral centres does gonane have?
6
353
Where are the chiral centres in gonane?
6 8 9 10 13 14
354
How many stereoisomers does gonane have?
64 theoretically but only a few occur in nature
355
What are the two main types of steroid hormones?
Corticosteroids Sex hormones
356
Where are the corticosteroids made?
Adrenal cortex
357
Where are the sex steroids made?
Gonads
358
What are the two types of corticosteroids?
Glucocorticoids Mineralcorticoids
359
What are the three types of sex steroids?
Androgens Progestogens Estrogens
360
Where do glucocorticoids bind?
Glucoreceptors
361
Where do mineralocorticoids bind?
Metal containing receptors
362
What is the precursor for steroid hormones?
Cholesterol
363
Effects of steroid hormones on genome pathways?
Binding of hormones to receptors causes configuration changes in the receptor which then has a regulatory effect on the DNA element
364
Effects of steroid hormones on non-genomic pathways?
Bind to ion channels and GCPRs Can have a direct effect on cell membrane
365
What type of steroid is dexamethasone?
Glucocorticoid
366
What can dexamethasone treat?
Rheumatic problems Skin disease Severe allergy Asthma COPD croup Brain swelling Covid-19
367
What does dexamethasone have such a broad effect?
It affects global receptors It is not specific to one area So it can cause side effects
368
Chemical structure of dexamethasone?
C22H29FO5 Usual steroid structure but with: - fluorinated at position 9 - hydroxy groups at positions 11, 17 and 21 - methyl group at position 16 - carbonyl (oxo) groups at positions 3 and 20
369
Dexamethasone mechanism of action?
1) enters the cell 2) binds to an intracellular receptor 3) heat-shock protein is hydrolysed, and releases activated steroid-receptor complex 4) steroid-receptor complex is transported into the nucleus 5) binds to DNA 6) modifies DNA glucocorticoid-responsive elements and transcription factors 7) this alters the transcription of target genes in DNA into mRNA 8) mRNA leaves the nucleus 9) mRNA directs the synthesis of new proteins on cytoplasmic ribosomes 10) these proteins are released from the cell and elicit a biological response
370
Effects of dexamethasone in low and high doses?
Reduces inflammation. An increase in the production of anti-inflammatory compounds such as annexin-1, SLP1, MOP-1, and nitric oxide synthase
371
Effects of dexamethasone only with high doses?
Immunosuppressive. Reduces the production of pro-inflammatory compounds, including cytokines, chemokines, adhesion molecules. Also, reduce the production of pro-inflammatory enzymes such as A2 and cyclooxygenase
372
Actions of anabolic androgenic steroids?
Building things up, such as muscle Regulate several genes associated with virilisation (development of male characteristics)
373
Why are females more prone to osteoporosis?
The androgenic steroids maintain skeletal integrity in males, whereas, in females, they develop the bones but do not maintain them
374
Types of synthetic anabolic androgenic steroids?
Testosterone Oxandrolone
375
Chemical structure of testosterone?
C19H28O2 It contains a ketone functional group at position 3 It contains a hydroxyl group at position 17
376
Chemical structure of oxandrolone?
C19H30O3
377
Effects of testosterone vs oxandrolone?
Androgenic : anabolic Testosterone 1:1 Oxandrolone 1:3-13 So oxandrolone has a much greater anabolic effect with less androgenic effects
378
Side effects of AAS’s?
Physiological issues Testicular shrinkage Heart attack Stroke High BP Male pattern baldness (in males and females) Breast growth in males Breast shrinkage in females
379
Why are steroids (cholesterol) important for cell membranes?
They can bind with other lipids to produce a liquid ordered membrane. The right levels is crucial.
380
What are the three types of drug used for the immune system?
Immunoglobulins Immunostimulants Immunosuppressants
381
What are IVIGs?
Antibodies isolated from patients to give to others Usually in the form of IgM and IgG
382
Limitations of IVIGs?
Hard to modify
383
Types of immunostimulants?
Vaccines Interferon (such as Pegasys) Interleukins (aldesleukin)
384
What are interferons? (as drug treatments)
Cytokines- proteins Have many different effects but usually either down-regulate or activate certain pathways
385
What are interleukins? (as drug treatments)
Proteins produced in response to an immune response and upregulate the response
386
What is an example of an interleukin? (as drug treatments)
Aldesleukin IL-2 Used for cancer cells by interfering with growth. It stimulates the immune system By encouraging the growth of killer T cells and other cells that attack cancer
387
What are immunosuppressants used for?
Reduce inflammation Reduce symptoms of autoimmune diseases Reduce allergic reaction Reduce transplant rejection
388
Types of immunosuppressants?
Calcineurin inhibitors (cyclosporin, tacrolimus) IL inhibitors (anakinra, tocilizumab) TNFa inhibitors (adalimumab, infliximab) Methotrexate Omalizumab (anti IgE) Azathioprine NSAIDs
389
How does cyclosporin work?
Forms complexes with cyclophilin to block phosphatase activity of calcineurin. This decreases the production of inflammatory cytokines by T cells.
390
How do NSAIDs work?
Inhibit cyclooxygenase that makes prostaglandins
391
How does methotrexate work?
Acts against rapidly dividing cells so can be used for cancer Bone marrow is also rapidly dividing, so it becomes an immunosuppressant
392
How does carbimazole work?
Inhibits conversion of T4 to T3 to the hormone cannot enter the cell
393
Why is agranulocytosis associated with carbimazole?
Carbimazole is myelotoxic (toxic to bone marrow), so therefore, a reduction in WBC can occur
394
What is DHF used for?
to covert to THF to make nucleic acids
395
Why can we target DHF in bacteria without harming the host?
Humans absorb DHF from the diet but bacteria need to synthesis their own so we can target this enzyme in this process
396
How do bacteria synthesise DHF?
P-aminobenzoic acid + pteridine ---\> dihydropteroate ---\> DHF With the help of the enzyme dihydropteroate synthetase
397
What is DHF?
Dihydrofolic acid
398
What is THF?
Tetrahydrofolic acid
399
When were sulfonamides discovered?
In 1935 Prontosil was used, it was a prodrug that metabolised by breaking a double bond between two nitrogens to sulphanilamide
400
Mechanism of action of sulfonamides?
Inhibit dihydropteroate synthetase in bacteria The sulfonamide is structurally similar to the natural enzyme-substrate, p-aminobenzoic acid Competitive inhibitors and classed as bacteriostatic
401
What kind of bonding is the red line?
Hydrogen bonds
402
What kind of bonding is the blue line?
Van der Waals interactions from benzene ring
403
What kind of bonding is the yellow line?
ionic bonding
404
What are the key chemical structures of sulfonamides?
1) aromatic ring 2) sulfonamide group 3) p-substitution only 4) sulfonamide N must be 1° or 2° (either one or two hydrogens present) 5) p-amino group must be 1° (one hydrogen group present) 6) if amino R group is an acetyl group it can act as a prodrug 7) sulfonamide R group is the only variable
405
Chemical structure of sulfonamides?
406
how many can sulfonamides be chemically changed?
Changing the R group on the sulfonamide group
407
How do prodrugs of sulfonamides work?
An amide group lowers the polarity of the sulfonamide and increases hydrophobic character as it cannot ionise but can then be hydrolysed into the active form. This allows the drug to cross the gut wall more easily
408
How are sulfonamides metabolism?
N-acetylation which increases hydrophobic character which reduces the aqueous solubility and can potentially lead to side effects so we need to try to increase the water solubility of the drug
409
How can we increase the water solubility of sulfonamides for metabolism?
We can change the R2 group so the sulfonamide N-H bond is more acidic. Converting sulfathiazole to sulfadiazine The pyrimidine ring of the sulfadiazine is more electron-withdrawing therefore making the negative ion formed more stable lowering the pKa of the sulfonamide N-H proton
410
What is sequential blocking?
Using a combination of drugs that inhibit different enzymes in the same biosynthesis pathway It allows lower, safer dose levels of each drug
411
General penicillin structure?
412
General cephalosporin structure?
413
What is the general structure of a beta-lactam?
Beta= size of ring Lactam= Cyclic amide
414
Mechanism of action of penicillins?
Inhibit an enzyme called transpeptidase which is needed for cell wall synthesis They are bacteriocidal Gram-positive are more susceptible The penicillin resembles the D-ala-D-ala residue (natural substrate), and the transpeptidase enzyme binds penicillin and catalyses C-N bond fission to give an acetyl enzyme that does not turn over
415
What is D-ala-D-ala?
Two alanine amino acid residues in a dipeptide structure
416
Why does penicillin react faster with the transpeptidase enzyme than the natural substrate?
Due to the strain of the four-membered ring A smaller bond angle than usual causes torsional strain meaning the molecules will more readily react to relieve the strain
417
Essential structure features of penicillin?
1) amide group 2) carboxylic acid/carboxylate 3) B-lactam ring 4) B-lactam ring as a bicyclic 5) variation limited to side chain R
418
How is penicillin G synthesised?
a standard nucleophilic acyl substitution reaction
419
Problems with penicillin G?
limited range of activity Not orally active as it's sensitive to stomach acid Sensitive to beta-lactamases
420
How to solve the problems of penicillin G?
Increase chemical stability for oral administration Increase resistance to B-lactamases Increase range of activity
421
How can we increase the acid-stability of penicillin?
Make the side-chain an electron-withdrawing group, drawing the electrons away from the carbonyl oxygen, making it less nucleophilic
422
How can we stop beta-lactamases?
Add steric Shields (bulky side chains) to stop penicillin from accessing the B-lactamase active site However, if they are too bulky, then it prevents penicillin from binding to the transpeptidase enzyme Give beta-lactamase inhibitors such as clavulanic acid
423
Essential structural features of cephalosporins?
1) B-lactam ring 2) Carboxylic acid at position 4 is important for binding 3) Bicyclic ring important for increasing ring statin 4) stereochemistry is important
424
Mechanism of action of vancomycin?
Blocks transglycosidation by providing a binding pocket for the biosynthetic building blocks and binds to the tail of the building blocks peptide chain Forms hydrogen bonds to the target and therefore acts as a receptor for the building block
425
How does vancomycin resistance occur?
Due to a mutation in a pentapeptide chain of cell wall building blocks where the terminal D-alanine is replaced by D-lactate
426
Tetracycline structure?