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Organic Flashcards

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1
Q

General formula

A

Algebraic formula that can describe any member of a family of compounds

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2
Q

Empirical form

A

Simplest whole number ratio of Elmer’s in a compound

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3
Q

Molecular formula

A

Acc n.o of atoms of each element in a molecule eg C4 H10 O

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4
Q

Structural formula

A

Shows the atoms carbon by carbon with attached hydrogens and functional groups eg CH3CH2CH2

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5
Q

Skeletal form

A

Shows bonds of carbon skeleton and any functional groups
Hydrogen and carbon atoms aren’t shown

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6
Q

Displayed

A

Shows how all atoms are arranged and all bonds between them

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7
Q

Homologous series

A

Group of compounds with same functional group and similar chemical properties

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8
Q

How does each successive member of homologous series differ

A

By a CH2 group

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9
Q

Functional group

A

Part of mol that determines how it reacts

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10
Q

What is nomenclature

A

Naming of organic molecules by IUPAC

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11
Q

Number of carbons for each prefix

A

Meth - 1 hex - 6
Eth - 2 Hept - 7
Prop - 3 Oct - 8
But - 4 Non - 9
Pent -5 Dec - 10

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12
Q

Alkanes functional group and suffix

A

C-C
- ane

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13
Q

Alkenes

A

C=C
-ene

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14
Q

Haloalkanes func group and prefix and suffix

A

C-X (X is halogen)
Chloro
Bromo
Fluoro
Iodo
- ane

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15
Q

Alcohol

A

OH
-anol

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16
Q

Aldehyde

A

CHO. O
||
C
\
H
Carbonyl group on the end of chain
- anal

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17
Q

Ketone

A

C(O)H
Carbonyl group in middle
- anone

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18
Q

Carboxylic acid

A

COOH
- anooic acid

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19
Q

Rules for naming
1)

A

Find longest carbon chain + count
To decide prefix ( meth eth prop etc)

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20
Q

2)

A

Look for func group and decide suffix (anol ene ane)

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21
Q

3)

A

Number func group w lowest number

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22
Q

4

A

Look for additional things attached to chain

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23
Q

5

A

Number additional things

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24
Q

Methyl group

A

CH3

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25
Q

Ethyl

A

CH2 - CH3

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26
Q

Where does number come

A

Before it’s thing in the chain

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27
Q

Prefix for 2 3 4 halogen

A

Di
Tri
Tetra

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28
Q

How are things arranged

A

Alphabetically

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29
Q

How do you number something with 2 of a thing eg carbon w 2 chlorine’s attached

A

2, 2 - di Choro

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30
Q

Between letters and numbers

A

Dash

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31
Q

Between numbers and numbers

A

Comma

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32
Q

How are alcohol groups named

A

Numbering occurs within the name
Eg pentan - 2 - ol

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33
Q

Structural isomers

A

Molecules with same molecular formula but different structural formula

Can be done by adding methyl groups

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34
Q

Functional group isomers

A

Molecules have same molecular formula but different functional groups

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35
Q

Chain isomers

A

Differ the arrangement of the hydrocarbon chain
Eg adding a branched methyl group

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36
Q

Positional isomers

A

Have diff postions of functional group on the hydrocarbon chain
Eg 1- chloro butane and 2 chloro butane

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37
Q

Stereoisomers def

A

Same structural formula but different arrangements of atoms in space

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38
Q

Single covalent bonds are….

A

Fully rotational

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39
Q

Double covalent bonds have ..

A

Restricted rotation

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40
Q

So isomers with restricted movement have their atoms …

A

Either on the same side or opposite sides

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41
Q

What are these isomers called

A

Geometrical isomers

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42
Q

If atoms on the same side they are ….. isomers

A

Cis isomers / Z isomers

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43
Q

Is atoms are on opposite sides they’re

A

Trans/ E isomers

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44
Q

geometric isomers aka

A

e/z isomers

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45
Q

What 2 conditions have to be met for Alkene to have e/z isomer

A

Double bond C —> must be attached to 2 diff groups/atoms
At least one of the groups must be the same on both carbon atoms on the double bond

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46
Q

Groups on Z isomer

A

The same side

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47
Q

Groups on E isomer are on the

A

Opposite side
Trans isomers

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48
Q

When naming E/Z isomers you put the…

A

E or Z before the isomer name

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49
Q

First CIP rule for E/Z isomers

A

Look at the atoms attached to the carbons on either side of the double bond
Element with greatest atomic number is given priority

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50
Q

So an isomer is an E isomer if via CIP

A

The highest priority groups are on opposite side

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51
Q

An isomer is a Z isosmer via CIP if

A

The highest priority groups are on the Same side

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52
Q

what is a hydrocarbon

A

mol that contains carbon and hydrogen atoms only

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53
Q

saturated …

A

singe carbon - carbon bonds
alkanes

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54
Q

unsaturated …

A

double carbon=carbon bonds
alkenes

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55
Q

what is crude oil

A

mixture of alkanes

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56
Q

sep crude oil by….

A

fractional distillation using fractionating column

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57
Q

how does frac dist work (hint bp)

A

sep alkanes based on bp that is determined by length of hydrocarbon chain
longer chain=higher bp
more van dew waals forces

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58
Q

frac column - how does it cool

A

heat crude oil
vapour in
crude oil vapour rises and will cool
short chains at top of colum - cooler
long chain at botton where its hotter
as it cools vapour will condesne when they reach their bp –> collected as fractions

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59
Q

cracking

A

breaking long chained alkanes into short more useful alkenes that are higher in demand and make more money due to low supply and high demand is short alkames and alkenes worth lots of money.

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60
Q

complete combustion prod

A

carbon dioxide and water

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61
Q

incomplete combustion prod

A

carbon monoxide (CO) and water
or carbon and water

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62
Q

test for alkenes

A

bromine sol
orange to colourless

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63
Q

alkenes used …

A

chemical feed stock
feuls
plastics

64
Q

what is petroleum and naphtha

A

crude oil
Naptha is petrol

65
Q

2 types of cracking

A

thermal cracking
catalytic cracking

66
Q

thermal cracking

A

high temp (700-1200k) and high pressure (7000kpa)
products :alkenes a lot more than catalytic
Applications: ethene used for making polymers and ethanol

67
Q

catalytic cracking

A

uses zeolite catalyst
high temp
slight pressure
produces aromatic, branched and cyclic hydrocarbons and used to make motor fuels and alkenes but far less than in thermal

68
Q

alkanes make great fuel bc and uses of fuels

A

burning small amounts rel lots of energy
for central heating and fuel to car engines

69
Q

downside of alkanes

A

rel lots of pollutants

70
Q

Steps of free radical substitution

A

Initiation
2 propagation
Termination

71
Q

Overall equation for methane + chlorine

A

Ch4 + CL2 —> CH3CL + HCL

72
Q

Initiation step for chlorine and methane

A

CL2 —-> cl . + cl.
. = free radical

73
Q

Free radical meaning

A

Species w unpaired e-

74
Q

conditions for initation and describe whagt happens

A

in presense of uv light breaks
cl - cl bond - via homolytic fission so each atom gets one e- from covalent bond

75
Q

describe propogation part 1 w methane and give equation

A

The chlorine free radicals are very reactive and remove
an H from the methane leaving a methyl free radical
CH4 + Cl. –> HCl + .CH3

76
Q

describe propogation part 2 w methane and give equation

A

The methyl free radical reacts with a Cl2 molecule to
produce the main product ( prod w one less h replaced w cl and another Cl free radical

77
Q

what is common in all propogation steps

A

All propagation steps have a free radical in the reactants and in the products.

78
Q

how do cl free radicals lead to chain reaction

A

As the Cl free radical is regenerated, it can react with several more
alkane molecules in a chain reaction.

79
Q

describe termination and give equation

A

2 radicals combine to form neutral mol
cl. + cl. –> cl2
.CH3 + Cl . –> CH3Cl
.CH3 +. CH3 –> CH3CH3
this stops the reaction

80
Q

What group will take priority using CIP rules for steroisoners

A

Group with highest atomic number takes priority

81
Q

Homologous series have the same

A

Same general formula
Same chemical properties
same functional group

82
Q

General formula for alkane

A

CnH2n+2

83
Q

General formula for cycloalkane and Alkene

A

CnH2n

84
Q

General formula for nalogenoalkanes

A

CnH2n+1X
X is the halogen

85
Q

General formula for alcoholism

A

CnH2n+1OH

86
Q

General formula for aldehyde and ketones

A

CnH2nO
C double bond to O and then H happens at the end of the chain (carbonyl group)
On ketone c double o bond in the middle

87
Q

General formula and functional group for carboxylic acid

A

CnH2nO2
R - C double O
THEN O -H at bottom

88
Q

General formula and fund group of amine

A

CnH2n+3n
R - NH2

89
Q

General form for nitriles

A

CnH2n-1
R - C tripled bond to N

90
Q

Usually when drawing functional group isomers you will have to draw…

A

An alkene ad a cycloalkane
An aldehyde and ketone
An alcohol and ether (C-O-C)
Carboxylix acid and ester COOC c double bonded to O

91
Q

Physical properties of alkanes

A

Non polar
Weak van den walls forces = now boiling point
Van her walls increase in strength if chain length increases boiling point increases
Branching of chain gives lower bp due to weaver vow

Insoluble in water as water is a polar solvent and acuanes are non polar

92
Q

Uses for alkanes

A

Quite unreactive because c-c bonds strong flammable so used as fuels
Used as a lubricant and to make other molecules like alkenes and halogenoaljanes

93
Q

Order of fractions from crude oil

A

@Top:
Petrol, kerosene, diesel oil, lubricating ail, fuel oil, bitumen (C70)

94
Q

Properties of shorter alkanes

A

Found at top of fractionating column where it cooler
Lower bp, more valitale, more flammable, less viscous more runny) and less coloured.

95
Q

How
Does thermal cracking work

A

Thermal cracking involves breaking a carbon-carbon bond.
● The bond breaks by heterolytic fission, so one electron from the bonding pair goes to each half of the molecule.
● This forms fragments of the original molecule called free radicals (species with an unpaired electron).
● In order to become more stable, the fragments become an alkane and an alkene (there are not enough hydrogens to form two alkanes)

96
Q

Structure of zeolite catalyst

A

Honey comb

97
Q

Reactivity of any mol depends on

A

Bond enthalpy The bond enthalpies of C—C bond and C—H bond are quite high that makes it difficult to be broken. A C—C bond has a bond enthalpy of 342 kJ/mol. A C—H bond has a bond enthalpy of 412 kJ/mol.
Bond polarity
Alkanes are non polar as Carbon and Hydrogen have similar electronegativities. Due to this, the bonds are difficult to be broken and this makes alkanes unreactive except towards free radicals. But alkanes reactive with oxygen in combustion reactions and with halogens in substation reactions (in the presence of sunlight).

98
Q

Incomplete combustion equation and examples

A

alkane + oxygen → carbon monoxide + water alkane + oxygen → carbon + water
For example:
propane + oxygen → carbon monoxide + water C3H8(g) + 31⁄2O2(g) → 3CO(g) + 4H2O(g)
propane + oxygen → carbon + water C3H8(g) + 2O2(g) → 3C(s) + 4H2O(g)

99
Q

Most common pollutants of combustion and incomplete combustion

A

Carbon monoxide - poisonous gas
Carbon particulates-soot-asthma+ cancer
Carbon dioxide and water vapour- green house gases
Sulphur dioxide _ acid-rain- S+O2
Nitrogen oxides - N2+o2 —> 2NO
Unburnt hydrocarbons - rise up into atmosphere and react w nitrogen oxides prod photochemical smog

100
Q

Nitrogen oxide as pollutant

A

Nitrogen oxides are produced due to high temperatures inside petrol engines. The oxides can dissolve in water in the atmosphere to form nitric acid and resulting in acid rain. Nitrogen oxides also contribute to photochemical smog

101
Q

Sulphur dioxide as a pollutant

A

Sulphur dioxide is produced by the combustion of fossil fuels which contain sulphur impurities. Sulphur dioxide dissolves in water in the atmosphere to produce acid rain.

102
Q

What is the greenhouse effect + why is it getting worse

A

The greenhouse effect is a naturally occurring process that has kept the Earth at a warm enough temperature for life to evolve and sustain.
However since the industrial revolution the massive increase in the combustion of fossil fuels has dramatically increased carbon dioxide levels in the atmosphere, leading to an enhanced greenhouse effect which causes the Earths average temperature to increase

Earth gets warmed up by visible radiation infrared from the sun, this can penantrale the gases in the atmosphere. Infrared emitted by earth, some passes into space,some trapped by gg in the atmosphere this traps radiation this warms the earth-warme enough tosupport life but now too warm due to fossil fuels releasing lots of co2

103
Q

Equation for nitrogen oxides

A

N2+O2→2NO
N2 + 2O2→2NO2

104
Q

Where are nitrogen oxides produced and what do they produce

A

In car engine

NO is toxic and produces smog. NO2 is toxic and produces acid rain.

105
Q

How can harmful gases produced by combustion be removed and what are they turned into
With equations

A

These harmful gases can be removed by using catalytic converters to convert these
gases in exhaust to carbon dioxide, nitrogen and water.
2CO + 2NO→2CO2 + N2
C8H18 + 25NO→ 8CO2 + 12.5N2 + 9H2O

106
Q

Catalysts in catalytic converter

A

platinum and rhodium
Expensive metals

107
Q

How to reduce costs of expensive metal catalysts used in catalytic converters

A

In order to reduce the cost and increase the effectiveness, the metals are coated onto a ceramic honeycomb, giving an enormous surface area for the reaction. The reactions take place on the surface of the catalyst

108
Q

2 reactions in catalytic converter And their equations

A

In the catalytic converter, Nitrogen oxide and carbon monoxide react together. While the nitrogen oxides are converted to harmless nitrogen, the cabon monoxide is converted into carbon dioxide.
2CO(g) + 2NO(g)→N2(g) + 2CO2(g)

• Unreacted hydrocarbons also react with nitrogen oxides to form
nitrogen and carbon dioxide and water.
C8H18 + 25NO→12.5N2 + 8CO2 + 9H2O

109
Q

How is sulphur dioxide formed and what does it go onto form

A

Petroleum fractions, coal and natural gas contain sulphur impurities that burn in the presence of oxygen to form sulphur dioxide.
S+O2 → SO2
CH3SH+ 3O2 → SO2 + CO2 + 2H2O

The sulphur dioxide combines with oxygen and water in the atmosphere to form sulphuric acid, which in turn produces acid rain.
SO2(g) +0.5O2(g) +H2O(l)→H2SO4(l)

110
Q

Removal of sulphur dioxide from waste gas happens during…

A

Flue gas desulfurisation - In power stations that burn coal or natural gas the sulphur dioxide that is produced is removed from the flue (waste) gases through a chemical reaction.

111
Q

1st step of flue gas desulfuration

A

Calcium oxide, which is a base, neutralises the acidic sulphur dioxide. It is then further oxidised to form calcium sulphate.

The overall reaction is;
CaO(s) + 2H2O(l) + SO2(g) + 0.5O2(g) → CaSO4.2H2O(s)

112
Q

flue gas desulfuration what happens to products formed

A

Calcium sulphate is then sold and used to make plasterboards and builders plaster.

113
Q

Alternative to using calcium oxide in flue gas desulturisation + equation + downsides

A

Alternatively, calcium carbonate can be used, however this process produces carbon dioxide. - this is a green house gas
CaCO3(s) + SO2(g) + 0.5O2(g) → CaSO4(s)+ CO2(g)

114
Q

Is crude oil renewable or non renewable?

A

Non renewable

115
Q

To conserve crude oil what is done

A

To conserve crude oil, alternative fuels are found by researchers.
• Alcohols and bio-diesel are examples of fuels with plant origin and hence, are renewable.
• Alcohol is produced by fermentation of sugars from plants and bio-diesel is produced by reacting vegetable oils with a mixture of alkali and methanol.

• Biodiesel is more carbon neutral which means that the emission of green house gases is reduced

• Hydrogen fuel cells use hydrogen gas and oxygen gas as its reactants and produce energy and water. This is an example of carbon neutral fuel

116
Q

what is a halogenalkane

A

alkane with halogen

117
Q

how can halogenoalkanes be classfied

A

Halogenoalkanes can be classified as primary, secondary or tertiary depending
on the number of carbon atoms attached to the C-X functional group.

118
Q

what is a primary halogenalkane

A

One carbon attached to the
carbon atom adjoining the
halogen

119
Q

what is a secondary halogenalkane

A

Two carbons attached to the
carbon atom adjoining the
halogen

120
Q

what is tertiary halogenalkane

A

Three carbons attached to the
carbon atom adjoining the
halogen

121
Q

what reactions do halogenoalkanes undergo

A

Halogenoalkanes undergo either
substitution or elimination reactions

122
Q

what is substitution reaction

A

swapping a halogen atom for another atom or groups of atoms
eg methane + chlorine —> chloromethane + hydrogen chloride

123
Q

what is a nucleophile

A

species w lone pair of electrons thta will attack an electron deficient species
has a neg charge
They are attracted to a positive charge or dipole on another molecule​

124
Q

3 nucleopiles

A

Common nucleophiles are hydroxide ions -:OH, ammonia :NH3, and cyanide ions -:CN​

125
Q

nuc sub reac beneficial bc

A

Nucleophilic substitution reactions are useful as they introduce new functional groups on to a molecule. This allows synthesis of specific molecules, eg pharmaceutical drugs.

126
Q

2 headed arrows in mechanisms show

A

movement of 2 e-

127
Q

why can nuc attack halogenoalkane

A

The polarity of the carbon-halogen bond makes it susceptible to nucleophilic attack.

128
Q

general equation for nuc sub

A

H H
| |
R - C - X + :Nu- –> R - C - Nu + :X
| |
H H

129
Q

halide ion prod by nuc sub of halogeno alkane known as

A

leaving group

130
Q

explain the mech for nuc sub

A

arrow from middle of delta pos C - X delta neg bond towards the x
arrow from nuc to delta pos carbon
nuc takes place of halogen - x
x now halide ion w lone pair and neg charge

131
Q

explain bond polarity of group 7

A

Going down group 7, the polarity of the bond decreases. ​

This is because the electronegativity of the halogens decreases going down the group. ​

The dipole on a halogenoalkane is not strong enough to form hydrogen bonds and so haloalkanes are not soluble in water. ​

The intermolecular forces between haloalkane molecules are dipole-dipole forces and van der Waals forces. ​

​

132
Q

least to most electro neg halogens

A

fluroine
chlorine
bromine
iodine

133
Q

explain boiling points of halogenoalkanes

A

Boiling points of halogenoalkanes increase with:​

Increasing carbon chain length​
The further down the group the halogen is.​

Both factors increase the number of electrons in the molecule and therefore increase the strength of the van der Waals forces. ​

Halogenoalkanes have higher boiling points than alkanes with similar chain lengths due to their higher molecular masses and polarity. ​

Branching of the halogenoalkane molecule lowers the melting point.​
​

​

134
Q

explain bond enthalpies of group 7

A

Going down group 7, the carbon-halogen bond enthalpy decreases. ​
Going down the group, the atomic radius of the halogen increases. ​
Fluorine being the smallest attracts the bonding pair of electrons most strongly towards its nucleus, giving the bond its strength. ​
Iodine being the largest atom has the weakest bond as the bonding pair of electrons is furthest from its nucleus.

135
Q

hydrolosis of halogenalkanes occurs when

A

When halogenoalkanes react with an aqueous solution hydroxide ions, a nucleophilic substitution reaction occurs, producing an alcohol and a halide ion. ​

For example, ​

 1-iodopropane + hydroxide       Propan-1-ol + iodide​
136
Q

what is the
chnage in funtional group
reagent
conditions
mechanism
and type of reagent
for nuc sub w aqeous hydroxide ions

A

Change in functional group: halogenoalkane –> alcohol
Reagent: potassium (or sodium) hydroxide
Conditions: In aqueous solution; Heat under reflux
Mechanism: Nucleophilic Substitution
Type of reagent: Nucleophile, OH-

137
Q

why is aqeous conditions important for nuc sub w oh- ion

A

The aqueous conditions needed
is an important point. If the
solvent is changed to ethanol
an elimination reaction occurs.

138
Q

what is the
chnage in funtional group
reagent
conditions
mechanism
and type of reagent
for nuc sub w cyanide ions

A

Change in functional group: halogenoalkane —> nitrile
Reagent: aqueous alcoholic potassium cyanide - ethanolic
Conditions: Heating under reflux
Mechanism: Nucleophilic Substitution
Type of reagent: Nucleophile, :CN-

139
Q

what does nuc sub w cyanide ions due to carbon chain and name of product formed

A

This reaction extends the carbon chain by one carbon, which must be reflected in the name of the product. The product will be named with the suffix –nitrile.

140
Q

products of Chloroethane + potassium cyanide

A

propanenitrile + potassium chloride​

141
Q

what is the
chnage in funtional group
reagent
conditions
mechanism
and type of reagent
for nuc sub w ammonium ions

A

Change in functional group: halogenoalkane –> amine
Reagent: NH3 dissolved in ethanol
Conditions: Heating under pressure (in a sealed
tube)
Mechanism: Nucleophilic substitution
Type of reagent: Nucleophile, :NH3

142
Q

how to name product of reaction of nuc sub with ammonia ion

A

The product is an amine R-NH2.​

Amines are named with the suffix –amine. ​

The stem of the name is named as alkyl. ​

​

143
Q

products of bromopropane + ammonia

A

Bromopropane + Ammonia –> propylamine + ammonium bromide​

CH3CH2CH2Br + 2NH3 —-> CH3CH2CH2NH2 + NH4Br​

144
Q

explain mechanism of nuc sub w ammonia

A

arrow from middle of C-X bond (respective delta neg and positive charges)
arrow from nh3 nuc to c

                                               h 
                                               | so now hal ion formed w       N- h
                                               | 
                                               h  takin its place

n from nh3 above msut have postive charge
then arrow from nh3 nuc toward bottom h on nh3 drawn above
and arrow from middle of drawn bond to postitive n

145
Q

what is the
chnage in funtional group
reagent
conditions
mechanism
and type of reagent
for elimination w oh ions

A

Change in functional group: halogenoalkane 
alkene
Reagents: Potassium (or sodium) hydroxide
Conditions: In ethanol ; heat
Mechanism: Elimination
Type of reagent: Base, OH

146
Q

differences in solvent for nuc sub and eliminatron

A

Note the importance of
the solvent to the type of
reaction here.
Aqueous: substitution
Alcoholic: elimination

147
Q

describe mech for elimnation w oh

A

https://chemrevise.files.wordpress.com/2021/02/3.3-revision-guide-halogenoalkanes-aqa.pdf
page 4

148
Q

what is ozone and its benefits

A

The naturally occurring ozone (O3
) layer in the upper
atmosphere is beneficial as it filters out much of the sun’s
harmful UV radiation

149
Q

what distrupts ozone layer

A

man made cfs (chloroflurocarbons)

150
Q

how do cfs distrupt ozone layer

A

(CFC’s) caused a hole to form in the ozone
layer. Chlorine radicals are formed in the upper atmosphere when energy from
ultra-violet radiation causes C–Cl bonds in chlorofluorocarbons (CFCs) to break forming chlorine free radical

151
Q

equation to show chlorine rad formation in cf2cl2

A

CF2Cl2 –> CF2Cl . + Cl.

152
Q

what does chlorine free radical go on to do and give equation

A

break down ozone mol to o2 mol
Cl. + O3 –> ClO. + O2

153
Q

chlorine rad acts as a _____ and so it not ____ __ so can be ______ and give equation for this

A

chlorine rad acts as a catalyst and so is not used up and can be regenerated
ClO. + O3 –> 2O2

154
Q

overall equation for ozone dep

A

2 O3 –> 3 O2

155
Q

what is now used instead of cfcs and why are they better

A

HFCs (Hydro fluoro carbons) e.g. CH2FCF3 are now used for refrigerators
and air-conditioners. These are safer
as they do not contain the C-Cl bond
The C-F bond is stronger than the C-Cl bond and is not affected by UV.

Chem (29 decks)

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