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organic 1 p2 Flashcards

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1
Q

nomenclature

A

system used for naming organic compounds

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2
Q

empirical formula

A

simplest whole number ratio of atoms in a molecules

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3
Q

molecular formula

A

provides the actual number of atoms of different elements in a molecule

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4
Q

displayed formula

A

shows every atom and every bond in a molecule

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5
Q

structural formula

A

shows the arrangement of atoms in a molecule without showing every bond

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6
Q

skeletal formula

A

a type of formula which is drawn as line with each vertex being a carbon atom
carbon atoms not drawn, assumed each C atom has all unspecified bonds as C-H

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7
Q

homologous series

A

a series of organic compounds having the same functional group but with each successive member differing by CH2

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8
Q

functional group

A

a group of atoms responsible for characteristic reactions of a compound

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9
Q

suffixes for..
aldehyde
ketone
carboxylic acid

A

aldehyde = al
ketone = one
carboxylic acid = oic acid

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10
Q

alkane formula

A

CnH2n+2

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11
Q

alkene formula

A

CnH2n

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12
Q

saturated

A

organic compounds which only contain single bonds

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13
Q

unsaturated compounds

A

organic compounds that contain at least one carbon carbon double covalent bond

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14
Q

structural isomerism

A

when molecules have the same molecular formula but different structural formula

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15
Q

what are 3 ways in which structural isomers can be formed?

A

1 alkyl groups can be in different places
2 functional groups can be bonded to different parts
3 there can be different functional groups

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16
Q

stereoisomers

A

organic compounds with the same molecular formula but have different arrangement of atoms in space

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17
Q

what is E-Z isomerism and how are the E and Z isomers decided?

A

caused by limited rotation about the C=C double bonds
if the two substituents with the highest molecular mass are on the same side on the double bond (both above/both below) it is the Z isomer

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18
Q

what is cis-trans isomerism?

A

special type of E/Z isomerism where the two substituents of each carbon atom are the same
E - trans
Z - cis

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19
Q

homolytic fission

A

happens when each bonding atom receives one electron from the bonded pair forming two radicals

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20
Q

heterolytic fission

A

when one bonding atom receives both electrons from the bonded pair

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21
Q

what are radicals?

A

highly reactive, neutral species

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22
Q

how is a covalent bond formed from two radicals?

A

radicals collide and the electrons are involved in the bond formation

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23
Q

how are alkane fuels obtained?

A

fractional distillation, cracking and reforming crude oil

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24
Q

fractional distillation process

A

1 oil pre heated and passed into a column
2 fractions condense at different temps (temp is hottest at bottom)
3 separation of the fuels depends on boiling point which depends son size of molecules - the larger the molecule the larger the London forces
4 similar molecules condense together and so are collected at the same fraction
5 small molecules condense at the top at lower temps and big molecules condense at the bottom at higher temps

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25
Q

cracking

A

process of converting large hydrocarbons to smaller molecules by breakage of C-C bonds

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26
Q

reforming crude oil

A

processing of straight chain hydrocarbons into branched chain alkanes and cyclic hydrocarbons for efficient combustion

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27
Q

shape and angle of an alkane?

A

tetrahedral
109.5

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28
Q

describe the sigma bond in alkane

A

the sigma bond is a covalent bond which has a direct overlap of the electron clouds of the bonding atoms

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29
Q

how reactive are alkanes?

A

very unreactive

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30
Q

what reactions do alkanes undergo?

A

combustion and reaction with halogens

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31
Q

what type of reaction is combustion?

A

oxidation reaction

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32
Q

what is complete combustion?

A

combustion that occurs with plentiful supply of air

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33
Q

what are the products of complete combustion when alkanes are used?

A

carbon dioxide and water

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34
Q

what is the colour of the bunsen flame during complete combustion?

A

blue flame

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35
Q

what is incomplete combustion and what products are formed in the case of alkanes?

A

combustion in a limited supply of oxygen
products: water, carbon dioxide and carbon monoxide

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36
Q

what type of hydrocarbon are most likely to undergo incomplete combustion?

A

longer chains

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37
Q

what are the pollutants formed in the combustion of alkanes?

A

carbon monoxide, oxides of nitrogen and sulfur, carbon particulates and unburned hydrocarbons

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38
Q

what is the environmental impact of carbon monoxide?

A

it is toxic/poisonous

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39
Q

what is the environmental impact of soot (carbon)?

A

asthma, cancer, global dimming

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40
Q

what are the environmental impacts of nitrogen oxides?

A

NO is toxic and can form smog
NO2 is toxic and acidic and forms acid rain

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41
Q

what are the environmental impacts of unbranched hydrocarbons?

A

they contribute towards formation of smog

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42
Q

what is the importance of catalytic converters?

A

these remove CO, nitrogen and unburned hydrocarbons (e.g. octane) from exhaust gases turning them into less toxic products CO2, N2 and H2O

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43
Q

what are biofuels?

A

fuels developed from renewable resources
alcohols and biodiesel are two examples of renewable plant-based fuels

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44
Q

what are the advantages of biofuels?

A

+
- reduces use of non-renewable fuels
- use of biodiesel is more carbon-neutral
- fossil fuels can be used feedstock for organic compounds
- less large scale pollution

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45
Q

what are the disadvantages of biofuels?

A
  • less food crops may be grown because crops for biofuel would be grown instead
  • reduction of rainforests have to be cut down to provide land
  • shortage of fertile soils
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45
Q

how are haloalkanes formed from alkanes

A

radical substitution

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46
Q

in the presence of what does alkane react with halogens?

A

UV light

47
Q

what are the 3 stages of free radical substitution?

A

initiation - breaking halogen bond to form free radicals
Cl2 –> 2Cl .
propagation - chain part of the reaction where products are formed but free radical remains
Cl. + CH4 –> HCl + .CH3
.CH3 + Cl2 –> CH3Cl + Cl.
termination - free radicals removed, stable products formed
.CH3 + Cl. –> CH3Cl
2Cl. –> Cl2
.CH3 + .CH3 –> CH3CH3

48
Q

what are the limitations of free radical substitution?

A

if there is excess halogen further substitution will take place therefore the desired product will be harder to separate from the others

49
Q

how is a pi bond formed?

A

electrons in the adjacent p orbitals overlap above and below the carbon atoms
they can only be made after a sigma bond is formed

pi bonds restrict the rotation of carbon atoms

50
Q

what is the angle and shape of a double bond?

A

trigonal planar 120*

51
Q

what is the qualitative test for alkenes?

A

this tests for C=C double bond using bromine water
if the alkene is present bromine water decolourises

52
Q

are alkenes(?) more or less reactive than alkanes? why?

A

more reactive due to high electron density of double bond and the fact the pi-bond is slightly easier to break

53
Q

what intermolecular forces of attraction do alkenes have?

A

only London forces due to non-polar bonds

54
Q

what are the types of isomers that can be formed using alkenes?

A

E/Z isomers - due to the restricted rotation
cis/trans isomers - if two of the same substituents are attached to each carbon

55
Q

what is an electrophile?

A

species that are electron pair acceptors

56
Q

what is the most stable type of carbocation intermediate? why?

A

alkyl groups have a positive inductive effect, so the most stable carbocation is the one bonded to the most other carbon atoms i.e. a tertiary carbocation

57
Q

major products will be formed from which kinds of carbocations?

A

tertiary (or the most stable available)

58
Q

what conditions are needed for the electrophilic addition of H2O to an alkene? what is this type of reaction called?

A

steam in the presence of an acid catalyst, usually phosphoric acid (H3PO4)
reaction is called hydration

59
Q

what is the product of the hydration reaction?

A

an alcohol

60
Q

what conditions are needed for the electrophilic addition of a hydrogen halide to an alkene?

A

hydrogen halide gases must be at room temperature

61
Q

what is the reaction called when a halogen is added to alkene?

A

halogenation

62
Q

how does a molecule with a non-polar bond react as if it is an electrophile?

A

C=C double bond with a high electron density induces a temporary dipole in the halogen molecule –> positive dipole atom attracted to double bond

63
Q

how can an alkene be converted into alkane? what is the reaction called and what are the required conditions?

A

alkene + hydrogen = alkane
hydrogenation
conditions –> 150*C nickel catalyst

64
Q

what is an addition polymer?

A

many monomers bonded together via rearrangement of bonds without the loss of any atom or molecule

65
Q

what are monomers? what form do they usually take?

A

molecules which combine to form a polymer
usually have a C=C bond which breaks to leave a repeating pattern

66
Q

what are the ways in which plastics can be disposed?

A

landfill, combustion, electricity generation, reuse, recycle, organic feedstock

67
Q

what are the disadvantages of recyling?

A

plastics must be sorted into different types, expensive, labour intensive, requires high technology

68
Q

how can chemists limit the problems caused by polymer disposal?

A

developing biodegradable polymers
removing toxic waste gases caused by incineration of plastics

69
Q

explain what happens in organic feedstock

A

plastics are separated and broken down into small organic molecules through a series of reaction
the molecules can then be used produce plastics and in other industries

70
Q

what are haloalkanes?

A

saturated organic compounds that contain carbon atoms and at least one halogen atoms

71
Q

are haloalkanes soluble in water?

A

insoluble as C-H bonds are non-polar not compensated for enough C-X bond polarity

72
Q

what type of intermolecular forces do haloalkanes have? why?

A

permanent dipole-dipole and London forces of attraction
C-X bond polarity creates permanent dipoles

72
Q

do haloalkanes have a polar bond? why?

A

yes polar, as halogen has a higher electronegativity than C (halogen is delta -, carbon is delta +)

73
Q

when would haloalkanes have higher boiling points?

A

increase Carbon chain length
halogen further down group 7 (e.g. I)

74
Q

how would the mass of a haloalkane compare with the mass of an alkane of the same chain length?

A

greater as mass of halogen > mass of H

75
Q

what is the most important factor in determining halogen reactivity?

A

the strength of carbon halogen bond

76
Q

what would bond polarity suggest the order of reactivity haloalkanes be?

A

C-F would be most reactive as most polar bond

77
Q

what would bond enthalpies suggest the order of reactivity of haloalkanes be?

A

C-I would be most reactive as lowest bond enthalpy

78
Q

what is the trend in reactivity of primary, secondary and tertiary haloalkanes?

A

tertiary halide produces a ppt almost instantly
secondary halide gives a slight ppt after a few seconds
primary halide takes considerably longer to produce a precipitate

79
Q

nucleophile

A

electron pair donor
e.g. OH-, CN-, NH3

80
Q

what is nucleophilic substitution?

A

a reaction where a nucleophile donates a lone pair of electrons to delta + C atom, delta - atom leaves molecule (replaced by nucleophiles)

81
Q

hydrolysis

A

a reaction where water is a reactant

82
Q

what reactant often produces hydroxide ions for hydrolysis?

A

water

83
Q

what fission does water undergo to produce OH-?

A

heterolytic fission

84
Q

what are the conditions/reactants needed for elimination reaction of haloalkanes?

A

NaOH or KOH dissolved in ethanol (no water present)
heated

85
Q

what is formed in elimination reaction of haloalkanes?

A

an alkene, water and halogen ion

86
Q

how can you convert a haloalkane into an amine?

A

reagent: NH3 dissolved in ethanol
conditions: heating under pressure in a sealed tube
mechanism: nucleophilic substitution
type of reagent: nucleophile - ammonia

87
Q

how do you convert haloalkane into alkene?

A

use ethanolic potassium hydroxide to produce alkenes (where the hydroxide ion acts as a base)

88
Q

how do you produce nitriles from haloalkane?

A

use potassium cyanide to produce nitriles (where the cyanide ion acts as a nucleophile)

89
Q

how can you compare the rate of hydrolysis of haloakanes?

A

aqueous silver nitrate is added to a haloalkane and a silver halide precipitation is formed
the quicker the precipitate is formed the faster the rate of hydrolysis
AgI(s) - yellow precipitate
AgBr(s) - cream ppt
AgCl(s) - white ppt
AgCl forms the slowest

90
Q

what is the functional group of an alcohol?

A

hydroxyl group -OH

91
Q

general formula of an alcohol

A

CnH2n+1OH

92
Q

alcohol prefix/suffix?

A

Hydroxyl-
-ol

93
Q

what kind of intermolecular forces do alcohols have? why?

A

hydrogen bonding, due to the electronegativity difference in the OH bond

94
Q

how do alcohols’ melting point and boiling point compare to other hydrocarbons’ of similar C chain lengths? why?

A

higher, because they have hydrogen bonding (strongest type of intermolecular force) –> stronger than London forces

95
Q

are alcohols soluble in water? why does solubility depend on chain length?

A

soluble when short chain - OH hydrogen bonds to hydrogen bond in water
insoluble when long chain - non polarity of C-H bond takes precedence

96
Q

what makes an alcohol primary?

A

C bonded to OH is bonded to one other C atom

97
Q

what makes an alcohol secondary?

A

C bonded to OH is bonded to two other C atoms

98
Q

what makes an alcohol tertiary?

A

C bonded to OH to three other C atoms

99
Q

what forms if you partially oxidise a primary alcohol?

A

an aldehyde

100
Q

what conditions are needed to partially oxidise a primary alcohol?

A

dilute sulfuric acid, potassium dichromate (VI). distil product as it’s produced, gentle heating

101
Q

write an equation for the partial oxidation of ethanol

A

CH3CH2OH(l) + [O] –> CH3CHO(g) + H2O(l)

102
Q

what forms if you fully oxidise a primary alcohol?

A

a carboxylic acid

103
Q

what conditions are needed to fully oxidise a primary alcohol?

A

concentrated sulfuric acid, potassium dichromate (VI), reflux, strong heating

104
Q

equation for the full oxidation of ethanol

A

CH3CH2OH(l) + 2[O] –> CH3COOH(g) +H2O

105
Q

what forms is you oxidise a secondary alcohol?

A

a ketone

106
Q

what conditions are needed for the oxidation of a secondary alcohol?

A

concentrated sulfuric acid, potassium dichromate (VI), strong heating

107
Q

is it possible to oxidise tertiary alcohol?

A

no

108
Q

what is a dehydration reaction?

A

a reaction where water is lost to form an organic compound

109
Q

what are the products of dehydration reaction of alcohol and the conditions needed?

A

alkene and water
conc sulfuric acid or conc phosphoric acid and 170*C

110
Q

how can you produce chloroalkanes from alcohols?

A

use PCl5 (PCl3/ conc HCl/ SOCl2 / mixture of NaCl + H2SO4 can all also be used for substituting a Cl)

e.g. CH3CH2OH + PCl5 –> CH3CH2Cl + POCl3 + HCl

111
Q

how can you produce bromoalkanes from alcohols?

A

use 50% conc sulfuric acid and potassium bromide

112
Q

how can you produce iodoalkanes from alcohols?

A

use red phosphorus and iodine
PI3 + 3CH3CH2OH –> 3CH2CH2I + H2PO3

113
Q

how do you prepare and purify of a liquid organic compound?

A

1 heat under reflux
2 extract with a solvent in a separating funnel
3 distil
4 dry with an anhydrous salt
5 determine boiling temperature

chemistry 2 (22 decks)

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