topic ten Flashcards

1
Q

what is catenation

A

the ability to form covalent bonds with itself, producing long chains and rings

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2
Q

homologous group

A

same general formula and functional group

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3
Q

In summary, a homologous series is a group of organic compounds that:

A

contain the same functional group,
have the same general formula,
differ by a CH2 group,
have similar chemical properties,
show a gradation in physical properties such as boiling point.

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4
Q

In full structural formulae, which bonds are shown

A

all

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5
Q

condensed structural forumlea

A

in which the bonds between atoms are omitted

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6
Q

skeletal formula

A

all atoms are omitted leaving only the backbone of the molecule.

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7
Q

sterochemical ormula

A

wedges and broken lines

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8
Q

isomers

A

same molecular formula but different arrangements of atoms

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9
Q

structural isomers

A

compounds with the same molecular formula but different arranagements of atoms

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10
Q

what categories can structural isomers be divided into

A

chain isomerism, position isomerism and functional group isomerism

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11
Q

functional groups

A

single atoms or groups of atoms that give organic compounds their characteristic properties

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12
Q

what is the bronsted lowry thing

A

donating or accepting a proton

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13
Q

waht is the lewis thing

A

donating or accepting an electron pair

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14
Q

what does iupac do

A

an international organisation that aims to establish a consistent system of nomenclature (naming) for organic compounds.

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15
Q

Alcohols that contain two hydroxyl functional groups are called

A

diols

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16
Q

ethers are made up of

A

two alkyl groups bodned by an oxygen atom

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17
Q

volatility of ethers

A

voltatile solvents beacaues theyre unable to form hydrogen bonds between molecules because they lack an oxygen atom directly bonded to a hydrogen atom

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18
Q

amines can be primary, secondary, teritary depening on

A

how many alkyl groups are bonded to the nitrogen atom of the amine group. Primary amines have one alkyl group, secondary amines have two and tertiary three.

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19
Q

The measure of how easily a substance evaporates is referred to as

A

its volatility

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20
Q

A highly volatile substance has a

A

low boiling point and evaporates easily

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21
Q

what are the three factors that determine voltaility

A

boiling point (increases with increasing molar mass as more intermolecular forces)

branched or not, branched chain isomers usually have lower boiling points than the corresponding straight chain isomers as branching produces a more spherical shape which results in less surface contact. Therefore, branched-chain isomers have weaker intermolecular forces and, consequently, lower boiling points

polar functional groups result in stronger dipole dipole interactions and therefore higher boiling points

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22
Q

how are dimers formed

A

through hydrogen bonds formed between two carboxyl groups on different molecules

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23
Q

compounds that are able to form hydrogen bonds with water molecules will be soluble in

A

water

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24
Q

as the length of the hydrogcarbon chain icnreases,

A

solubility decreases

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25
Q

hydrophobic character increases alongside

A

size of hydrocarbon chain

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26
Q

what is a phenyl functional group

A

benzene ring (aromatic compounds contain a benzene ring)

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27
Q

evidence for benzene

A

all carbon to carbon bond lengths are identical

only one isomer exists and there should be more if benzene consisted of alternating single and double bonds

enthalpy change for hydrogenation of benzene is less exothermic than expected

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28
Q

benzene takes part in substitution reactions rather than

A

addition

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29
Q

The enthalpy change for the hydrogenation of benzene is less than three times the value for the

A

hydrogenation of cyclohexene.

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30
Q

why are alkenes relatively unreactive

A

The carbon–hydrogen bonds are considered to be non-polar (or weakly polar) bonds, because of the small difference in electronegativity of 0.4 units.

The carbon–carbon and carbon–hydrogen bonds are relatively strong covalent bonds. This means that the alkanes are kinetically stable unless supplied with enough energy to overcome the energy barrier (the activation energy) for the reaction.

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31
Q

what is a saturated compound

A

one that has only carbon carbon single bonds

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32
Q

what is an unsatured compound

A

one that has double or triple bonds

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33
Q

alkanes are used as fuels because

A

they release large amounts of heat and are used extensively as fuels

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34
Q

If the oxygen supply is limited, however, the products are either

A

carbon monoxide (CO) and water, or solid carbon (also known as soot) and water.

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35
Q

what undergoes free radical substitution

A

alkanes with halogens

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36
Q

requirements for free radical sub

A

uv radiation

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37
Q

what is a substition reaction

A

involves the replacement of an atom or group of atoms with another atom or group. In the reaction between an alkane and a halogen, a hydrogen atom is replaced by a halogen atom such as chlorine.

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38
Q

why is free radical known as photochemical reactions

A

because they only take place in the presence of uv radiation

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39
Q

three steps of free radical sub

A

initation
propagation
termination

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40
Q

The initiation, propagation and termination steps for the reaction of methane and chlorine

A
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41
Q

when does homolytic bond fission occur

A

occurs when a bond breaks evenly, with each atom taking one electron from the bond. This results in the formation of radicals, or free-radicals, highly reactive species with unpaired electrons.

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42
Q

why are alkenes more reactive than alkanes

A

because of the double bond

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43
Q

what is hydrogenation `

A

In a hydrogenation reaction, gaseous hydrogen (H2) is added across the carbon-carbon double bond. The product of the reaction is an alkane, a saturated hydrocarbon

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44
Q

conditions for hydrogenation

A

high pressure and a nickel catalyst

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45
Q

how is hydrogenation used by the margarine industry

A

to convert veg oil containing unsat hydrocarbon chains to more saturated compounds with higher melting points

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46
Q

hydration of an alkene involves

A

the reaction of an alkene with steam in the presence of a sulfuric acid (H2SO4) or phosphoric acid (H3PO4) catalyst to produce an alcohol

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46
Q

how is hydration used

A

This reaction is used in industry to produce alcohols such as ethanol and butan-2-ol from alkenes.

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47
Q

what is halogenation

A

Alkenes react with halogens to produce dihalogenoalkanes. Such reactions take place readily at room temperature and are indicated by the decolourisation of the reacting halogen. The halogen atoms bond across the carbon-carbon double bond

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48
Q

how to test for alkenes

A

Bromine, Br2 (l), is added to both samples, which are then shaken. At room temperature, the brown colour of the bromine is immediately DECOLOURISED by the alkene. The mixture of bromine and the alkane shows no colour change. Note that the test for unsaturation can also be carried out with bromine water, Br2(aq), in which case a different product is formed.

BROWN TO COLOURLESS

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49
Q

what is addition polymerisation

A

Individual alkene molecules (monomers) can bond together to form long chains which are known as polymers.

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50
Q

summarisation of a polymerisation reaction

A
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51
Q

what is a repeating unit

A

A repeating unit is the part of a polymer chain whose repetition would produce the complete polymer chain, except for the end-groups.

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52
Q

PVC uses

A

one of the world’s most important plastics, with a wide range of uses including construction materials, packaging and covers for electrical cables. However, its widespread use is somewhat controversial because its synthesis is associated with toxic by-products called dioxins.

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53
Q

formation of the polymer PVC

A
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54
Q

formation of PTFE

A
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55
Q

PTFE uses

A

This polymer is used extensively for its non-adhesive surface properties. It is widely used in non-stick cooking pans, and is also part of waterproof and breathable fabrics such as Gore-tex®.

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56
Q

uses of PS

A

insulation, packaging

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57
Q

use of PP

A

crates and boxes, plastic rope

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58
Q

how is ethanol made from alcohol

A

bioethanol made by the combustion of alcohol

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59
Q

alcohol is oxidised to produce

A

ethanoic acid, main component of vinegar

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60
Q

The presence of the hydroxyl functional group makes alcohols susceptible to oxidation in the presence of a suitable oxidising agent. Suitable oxidising agents include

A

potassium manganate(VII) and acidified potassium dichromate(VI) (Cr2O72−/H+)

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61
Q

the dichromate ion forms an orange solution which changes to a ?? colour when it is reduced ot the Cr3+ ion

A

green

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62
Q

An alternative oxidising agent is acidified potassium manganate(VII) solution which changes colour from purple to ??? as the manganate(VII) ion, MnO4-, is reduced to the manganese(II) ion, Mn2+.

A

colourless

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63
Q

The partial oxidation of a primary alcohol produces an

A

aldehyde

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64
Q

If the aldehyde is the desired product, it can be removed as it forms by

A

distillation

This is possible because the boiling point of the aldehyde is lower than that of both the alcohol and the carboxylic acid. As the aldehyde evaporates and rises up the distillation column, it passes through the condenser where it condenses back to a liquid and runs down into the flask.

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65
Q

the complete oxidation of a primary alochol produces…

A

a carboxylic acid
heat under reflux with an excess of the oxidising agent

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66
Q

oxidation of secondary alcohol

A

ketone wtih acidified potassium dichromate

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67
Q

do tertiary alcohols undergo oxidation reactions

A

no

68
Q

when are esters formed

A

in reactions between alcohols and carboxylic acids

69
Q

what happens in an esterification or condensation reaction

A

two smaller molecules combine to form a larger molecuels (an ester) resulting in the loss of a molecule of water

70
Q

A carboxylic acid and an alcohol react to form what

A

a carboxylic acid and an alochol

71
Q

Esters are named from the alcohol and carboxylic acid from which they are formed. The name of the alcohol changes to

A

the alkyl group (such as ethyl, methyl, etc.). This is followed by the name of the carboxylic acid, with the ending changed to -oate.

72
Q

uses of esters

A

Esters are volatile organic compounds with distinctive aromas. For this reason, they are used in synthetic flavours, perfumes, and cosmetics. For example, 3-methylbutyl ethanoate (Figure 14) has an aroma similar to bananas and pears. Certain esters are also used as solvents in lacquers, paints and varnishes.

73
Q

what are halogenoalkanes

A

compounds that have one or more hydrogen atoms replaced by a halogen atom

74
Q

Halogenoalkanes undergo ??? reactions in which an atom or group of atoms are replaced by another atom or group

A

substitution

75
Q

what is a nucleophile

A

an electron-rich species with a lone pair of electrons that is attracted to regions of positive charge.

76
Q

what type of bond fission in halogenoalkane substition reactions

A

heterolytic bond fission with the halogen atom taking both the bonding electrons.

77
Q

In heterolytic bond fission,

A

a bond breaks with one atom in the bond taking both of the bonding electrons. This results in the formation of oppositely charged ions.

78
Q

why is benzene stable

A

due to the delocalised electrons within its structure

79
Q

why does benzene undrdergo substitution reactions

A

If benzene were to undergo addition reactions, it would result in the disruption of the ring structure and the loss of stability of the molecule. Therefore, benzene undergoes substitution reactions in which one atom (in this case a hydrogen atom) is replaced by a different atom. This does not cause disruption of the ring structure and is more energetically favourable for the benzene molecule. The delocalised ring of electrons, which represents an area of electron density (Figure 1), is also the site of reactivity. This region of electron density is attractive to species which are known as electrophiles.

80
Q

electrophiles

A

species that are electron deficient, and as such, they have either a positive charge or a partial positive charge

81
Q

The nitration of benzene.

A
82
Q

An electrophilic substitution reaction involves the

A

replacement of a hydrogen atom with an electrophile.

83
Q

The chlorination of benzene. ( or any halogen)

A
84
Q

The equation for the complete combustion of benzene

A

2C6H6 (l) + 15O2 (g) → 12CO2 (g) + 6H2O (l)

85
Q

What is the product when chlorine (Cl2) reacts with benzene in the presence of an aluminium chloride (AlCl3) catalyst?

A

C6H5Cl

86
Q

what are the two types of nucleophilic substitution

A

SN1 (substitution nucleophilic unimolecular) and SN2 (substitution nucleophilic bimolecular)

87
Q

what does a nucleophilic substition reaction involve

A

A nucleophilic substitution reaction involves the replacement of an atom or group of atoms with another atom or group of atoms. A nucleophile is a species with a lone pair of electrons or a negative charge that is attracted to a region of positive charge (nucleophiles are also Lewis bases).

88
Q

why is the carbon bonded to the halogen in a halogenoalakane open to attack by a nucleophile

A

its electron-deficient because of the difference in electronegativity between carbon and a halogen such as chlorine

89
Q

Each of these nucleophiles will replace the halogen atom, which leaves as a halide ion (known as the

A

leaving group)

90
Q

which halogenoalkanes undergo SN2 reactions

A

primary

91
Q

is sn2 one step or two step

A

one step

92
Q

describe sn2

A

It is a one-step mechanism in which the nucleophile attacks the electron-deficient carbon atom in what is known as a ‘back-side attack’. The attack of the nucleophile is coupled with the departure of the halide ion, which takes place simultaneously in this one-step process.

93
Q

what does bimolecular refer to

A

the molecularity of the rate determining step

94
Q

what is back side attack

A

a term used to refer to the approach of the nucleophile to the electron-deficient carbon from the opposite side of the leaving group.

95
Q

steps of sn2

A

formation of an unstable transition state in which both the nucleophile and the halogen atom are weakly bonded to the carbon atom; note that these partial bonds are represented by dashed lines. The carbon-to-halogen bond then breaks heterolytically, with the halogen atom taking both the bonding electrons. This results in the formation of a halide ion, X− (the leaving group). The product formed is a primary alcohol.

96
Q

why is the sn2 reaction described as being stereospecific

A

The backside attack of the nucleophile causes the inversion of the spatial arrangement of the other groups or atoms around the carbon atom.

97
Q

A stereospecific reaction is one in which there is only one possible

A

stereochemical outcome

98
Q

what do the reaction kineticds of the sn2 mechanism show

A

the rate of the reaction depends on the concentration of both the halogenoalkane and the nucleophile – the rate-determining step is bimolecular.

99
Q

does the transition state show up high or low on the energy profile

A

highest point

The energy level profile for the reaction above is shown in Figure 4. Note the formation of the high energy transition state, which represents a halfway stage in the reaction. At this point, covalent bonds between the nucleophile and the halogen atom are simultaneously being broken and made.

100
Q

which halogenoalkanes undergo sn1 reactions

A

tertiary

101
Q

is sn1 one step or two step

A

two step

102
Q

describe sn1

A

The SN1 mechanism is a two-step reaction and the first step of the reaction involves the breaking of the carbon–halogen bond. This bond breaks heterolytically, with the halogen atom taking both the bonding electrons, resulting in the formation of a carbocation intermediate. Figure 5 shows the first step in the mechanism for the reaction between 2-bromo-2-methylpropane (a tertiary halogenoalkane) and sodium hydroxide. Note the use of a curly arrow to show the movement of a pair of electrons from the C–Br bond to the bromine atom, and the formation of the carbocation when the bond breaks heterolytically. The carbocation formed has a trigonal planar arrangement with the carbon atom being sp2 hybridised.

In the second step of the reaction, the nucleophile uses a lone pair of electrons to form a bond with the carbocation intermediate (Figure 6). Once again, this is shown by the use of a curly arrow from the lone pair of electrons on the nucleophile (the hydroxide ion) to the electron-deficient carbon atom. The compound formed is the tertiary alcohol 2-methylpropan-2-ol.

103
Q

The ‘1’ in SN1 refers to the ??? of the rate-determining step, which is unimolecular.

A

molecularity

104
Q

the reate of reaction of sn1 depends on

A

the concentration of the halogenoalkane only

105
Q

which step ahs the highest activation enerfy in sn1

A

the first step. The second step has the lower activation energy because of the attraction between the oppositely charged ions.

106
Q

what is steric hinderance

A

The three bulky methyl (CH3) groups bonded to the carbon atom in the tertiary halogenoalkane make it difficult for the incoming nucleophile to attack from the backside

107
Q

what is the positive inductive effect

A

The carbocation is stabilised by each of these methyl groups having an electron-donating effect

108
Q

SN1 are favoured by waht type of solvent

A

protic polar

109
Q

SN2 reactions are favoured by

A

aprotic polar solvents

Unlike polar protic solvents, polar aprotic solvents cannot form hydrogen bonds with the nucleophile. This maintains the reactivity of the nucleophile, favouring the SN2 mechanism.

110
Q

Factors affecting the rate of nucleophilic substitution

A

The classification of the halogenoalkane.
The nature of the nucleophile
The leaving group.

111
Q

how does The classification of the halogenoalkane affect rate of nuc. sub

A

Tertiary halogenoalkanes react faster via the SN1 mechanism than primary halogenoalkanes do via the SN2 mechanism. The order in terms of rate of reaction (fastest first) is:

3o > 2o > 1o

112
Q

how does the nature of thenucleophile affect rate of nuc sub

A

The effectiveness of a nucleophile depends on its electron density; negatively-charged anions tend to be more reactive than neutral species. This explains why the hydroxide ion is a better nucleophile than a water molecule. The hydroxide ion has a negative charge, whereas the water molecule only has a negative dipole.

113
Q

how does the leaving group affect rate of nuc sub

A

The iodide ion is the best leaving group of the halide ions. This is due to the relative bond enthalpies: the C–I bond (228 kJ mol−1) is weaker than both the C–Br bond (285 kJ mol−1) and the C–Cl bond (324 kJ mol−1). In terms of rates of reaction, iodoalkanes react faster than bromoalkanes, which react faster than chloroalkanes.

114
Q

hat do sn1 reactions begin and end with

A

SN1 reactions begin with a single enantiomer and result in the production of a racemic mixture containing equal amounts of two enantiomers.

115
Q

what do sn2 reactions begin and end with

A

SN2 reactions begin with a single enantiomer and produce only one enantiomer which means that the final product is optically active.

116
Q

what is a racemic mixture known as

A

optically inactive

117
Q

what do electrophilic addition reactions invovle

A

addition of atoms or groups of atoms across the carbon carbon double bond

118
Q

what is a double bond composed of

A

one sigma bond and one pi bond

119
Q

During an addition reaction, which bond is broken

A

the weaker pi bond is broken and the atoms that make up the electrophile bond with the two carbon atoms that make up the carbon=carbon double bond.

120
Q

why are alkenes more reactive

A

because of the high electron density of the double bond which is attractive to species known as electrophiles

121
Q

an electrophile is either

A

positively-charged or electron-deficient

122
Q

why are there two possible products when hydrogen halides undergo reactions with an asymmetric alkene

A

major or minor depending on which carbon the hydrogen boinds to

123
Q

markovnikovs rule

A

states that when hydrogen halides add to asymmetric alkenes, the hydrogen atom bonds to the carbon atom that is already bonded to the greatest number of hydrogen atoms.

124
Q

markovnikov why

A

order of carbocation stability
3o > 2o > 1o

125
Q

interhalogens

A

compounds composed of two or more different halogen atoms

126
Q

The delocalised pi system, with its region of high electron density, makes the benzene molecule susceptible to attack by

A

electrophiles

127
Q

when benezene undergoes elec sub what happens

A

a hydrogen atom is replaced by an electrophile

128
Q

An energy profile of the electrophilic substitution of benzene

A

increase in energy when the delocalised pi (π) system becomes disrupted; also note the decrease in energy when the π system is reformed in the substituted product. The high activation energy required for the reaction to take place is another testament to the stability of the benzene molecule.

129
Q

The substitution of an electrophile into a benzene ring. Note that the delocalised pi (π) system is restored.

A

A pair of electrons (represented by a curly arrow) moves from the π system to create a bond with the electrophile. This results in the formation of an unstable carbocation intermediate. Note that the delocalised pi system has been disrupted as discussed previously. The restoration of the stable delocalised pi system is achieved by the loss of a proton (H+) from the carbocation intermediate.

130
Q

what does benzene react with to form nitrobenzene

A

Benzene reacts with a mixture of concentrated nitric acid and sulfuric acid (known as a nitrating mixture) to form nitrobenzene, C6H5NO2.

131
Q

nitration of benzene equation

A

2H2SO4 + HNO3 ⇌ NO2+ + 2HSO4− + H3O+

132
Q

mechanism for the nitration of benzene

A
133
Q

conditions for the nitration of benezene

A

The conditions for this reaction are heat under reflux to 50°C; note that the temperature should not be raised higher than 50°C as further nitration to dinitrobenzene will occur.

134
Q

carbonyl group

A

C=O

135
Q

how to reduce an aldehyde to a primary alcohol again

A

the reduction of an aldehyde, propanal, to a primary alcohol, propan-1-ol. The reducing agent is sodium borohydride (lithium aluminium hydride can also be used) followed by the addition of an acidic solution (H+).

136
Q

how to reduce a ketone to a secondary alochol again

A

the reduction of a ketone, propanone, to a secondary alcohol, propan-2-ol. The reducing agent is sodium borohydride followed by the addition of an acidic solution. As with the reduction of aldehydes, it is also possible to use lithium aluminium hydride as the reducing agent.

137
Q

how to reduce a carboxylic acid to a primary alcohol again

A

The reduction of carboxylic acids requires the use of the stronger reducing agent, lithium aluminium hydride (LiAlH4), in dry ether.

138
Q

can you stop the reactioon of carboxylic acid and lithium aluminum hydride when its an aldehyde

A

no it reacts too quickly

139
Q

how is the reduction of nitrobenzene

A

two stage reduction reaction

Firstly, nitrobenzene, C6H5NO2, is heated under reflux (using a boiling water bath) together with a mixture of tin (Sn) and concentrated hydrochloric acid. The product, the phenylammonium ion, C6H5NH3+, is protonated as the reaction is carried out under strongly acidic conditions. In the second stage, the phenylammonium ion is deprotonated to produce phenylamine by reacting with sodium hydroxide solution.

140
Q

In the first stage, nitrobenzene is reacted with tin in an acidic solution to form tin(II) ions, the phenylammonium ion and water. The equation for this reaction is:

A

C6H5NO2 (l) + 3Sn (s) + 7H+ (aq) → C6H5NH3+ (aq) + 3Sn2+ (aq) + 2H2O (l)

141
Q

In the second stage, the phenylammonium ion is reacted with hydroxide ions to form phenylamine (aniline) and water:

A

C6H5NH3+ (aq) + OH– (aq) → C6H5NH2 (l) + H2O (l)

142
Q

what is retrosynthesis

A

One method of devising organic compounds involves starting with the desired product (the target molecule) and working backwards – a technique known as retrosynthesis. By looking at the functional groups on the target molecule, chemists can identify the preceding steps in the synthesis, starting with readily available materials. This can be summarised as shown below:

target molecule ⇒ precursors ⇒ starting materials

143
Q

what is stereoisomerism

A

Stereoisomers have the same structural formula but differ in the spatial arrangement of atoms

144
Q

how can stereoisomers be divided

A

configurational isomers and conformational isomers

145
Q

config isomers

A

cannot be converted by rotations about single bonds

146
Q

conformational isomers

A

are compounds that can be converted just by rotations about single bonds

147
Q

optical isomers

A

are mirror images showing chirality

148
Q

newman projections

A

used to represent conformers (conformational isomers)

149
Q

The difference in energy between the two conformers

A

torsional strain

150
Q

According to the Cahn–Ingold–Prelog (CIP) priority rules

A

the atom with the highest atomic number on each carbon atom in the double bond is assigned the highest priority.

151
Q

if both high priority groups are on the same side…

A

z isomer

152
Q

if both high priority groups are on different sides

A

e isomer

153
Q

in which molecules does optical isomerism occur in

A

chiral molecules with a chiral centre

154
Q

what is an asymmetric/chiral carbon atom

A

one that is bonded to four different atoms or groups

155
Q

enantiomers

A

two stereoisomers that are mirror images of eachother

156
Q

how many optical isomers are there for an organic molecule with n chiral centres

A

2^n

157
Q

what is non sueprimposable

A

it is not possible to superimpose one enantiomer onto another

158
Q

two enantiomers are said to be optically active, meaning

A

they rotate the plane of plane polarised light

159
Q

Plane-polarised light is produced when

A

unpolarised light is passed through a polarising filter (Figure 3). If a vertical polarising filter is used, then only the vertical plane passes through. The plane of light that passes through the filter is known as plane-polarised light.

160
Q

do the two enantiomers have identical chemical and physical properties

A

yes apart from their interaction with plane polarised light

161
Q

how to distinguish between enantiomers

A

When plane-polarised light is passed through a solution of each enantiomer, they rotate the plane of the plane-polarised light in equal but opposite directions.

162
Q

what composes a polarimeter

A

The rotation of the plane of plane-polarised light by the two different enantiomers can be measured using a polarimeter (Figure 4). A polarimeter comprises a light source, two polarising filters (one fixed and one that can be rotated) and a tube that contains a solution of the enantiomer.

163
Q

operation of a polarimeter

A

Unpolarised light is passed through a polarising filter, which produces plane-polarised light.

The plane-polarised light passes through a solution of the enantiomer.

An analyser is used to determine the angle of rotation of the plane of the plane-polarised light.

164
Q

When both enantiomers are present in the solution in equal amounts, the two opposite rotations of the plane of the plane-polarised light will cancel each other out. Such a mixture is said to be

A

optically inactive and is referred to as a racemic mixture

165
Q

what are disastereoisomers or diastereoisomers

A

Some molecules do not have opposite configurations at all of the chiral centres and so are not mirror images of each other.

166
Q

can diastereoisomers be optically active

A

yes but some are not

167
Q
A
168
Q

which reagents are needed to convert nitrobenzene to phenylamine in 2 steps?

A
  1. tin and conc HCl
  2. sodium hydroxide