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Chemistry Year 12 > 6 - Organic Chemistry I > Flashcards

6 - Organic Chemistry I Flashcards

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1
Q

What is a hydrocarbon?

A

It is a compound consisting of hydrogen and carbon only.

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2
Q

What does saturated mean?

A

A hydrocarbon containing single carbon-carbon bonds only.

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3
Q

What does unsaturated mean?

A

A hydrocarbon containing a C=C double bond.

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4
Q

What is molecular formula?

A

The formula which shows the actual number of each type of atom in the molecule.

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5
Q

What is empirical formula?

A

Shows the simplest whole number ratio of atoms of each element in a compound.

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6
Q

What is general formula?

A

It is the algebraic formula for a homologous series.

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7
Q

What angle is the HCH bond in C2H6? and shape of the molecule?

A

Tetrahedral. 109.5°

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8
Q

What is a homologous series?

A

Families of organic compounds with the same functional group and same general formula.

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9
Q

What is a functional group?

A

An atom or a group of atoms which when present in different molecules, causes them to have similar chemical properties.

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10
Q

Functional group of aldehydes?

A

COH

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11
Q

functional group of carboxylic acids?

A

COOH

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12
Q

functional group of ketones?

A

CO (with carbons on either side of the carbon with the oxygen bonded to it).

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13
Q

functional group of esters?

A

COO

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14
Q

What is the prefix for alcohol groups?

A

hydroxy-

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15
Q

What is a structural isomer?

A

They are molecules with the same molecular formula but with different structures.

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16
Q

What are the different types of structural isomers?

A
  • chain isomerism
  • position isomerism
  • functional group isomerism.
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17
Q

What are chain isomers?

A

Compounds with the same molecular formula but different structures of the carbon skeleton.

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18
Q

What are position isomers?

A

Compounds with the same molecular formula but different structures due to different positions of the same functional group on the same carbon skeleton.

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19
Q

What are functional group isomers?

A

Compounds with the same molecular formula but with atoms arranged differently to give different functional groups.

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20
Q

What is an example of a functional group isomer?

A

alkene and cycloalkane with the same number of carbons and hydrogens.

  • general formula for alkenes and cycloalkanes are the same.
  • cycloalkanes are a functional group isomer of alkenes.
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21
Q

what are stereoisomers?

A

They are compounds with the same structural formula but have a different spatial arrangement of atoms.

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22
Q

What kind of isomerism can only be exhibited by alkenes?

A

E-Z steroisomerism

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23
Q

Why does E-Z stereoisomerism occur?

A
  • There is restricted rotation around the C=C double bond.

- There are two different groups/atoms attached to each carbon in the double bond.

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24
Q

Naming E and Z steroisomers?

A
  • if the priority group/atom is on the same side of the double bond, Z (together)
  • if the priority group/atom is on opposite sides of the double bond, E (opposite).
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25
Q

If the two priority groups are the same, what are the isomers called instead of E/Z?

A
  • instead of E, trans.

- instead of Z, cis

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26
Q

General formula for alkanes?

A

CnH2n+2

- they are saturated hydrocarbons.

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27
Q

How are alkane fuels obtained?

A

They are obtained from the fractional distillation, cracking and reforming of crude oil.

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28
Q

What does crude oil consist of?

A

A mixture of hydrocarbons with different chain lengths and different boiling points.

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29
Q

What are the stages of fractional distillation?

A
  • crude oil is vaporised
  • it is then passed into a fractionating column
  • the vapour is cooled as it rises
  • hydrocarbons condense at different heights based on boiling points
  • mixtures of similar fuels called fractions are collected
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30
Q

What is cracking

A

The conversion of long chain hydrocarbons to smaller hydrocarbon molecules by the breaking of C-C bonds.
- High Mr alkanes -> smaller Mr alkanes + alkenes.

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31
Q

Economic reasons for catalytic cracking?

A
  • shorter chain hydrocarbons are higher in demand (e.g petrol and naptha) than larger fractions.
  • to make use of excess larger hydrocarbons and supply the demand for short chain hydrocarbons.
  • products of cracking are more useful and valuable than the starting materials.
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32
Q

What is reforming?

A

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

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33
Q

What is complete combustion and what are the products?

A
  • alkanes burn with complete combustion in excess oxygen.

- CO2, H2O.

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34
Q

What is complete combustiinon and what are the products?

A
  • alkanes burn with incomplete combustion in limited amounts of oxygen
  • CO/C, H2O
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35
Q

Environmental consequences of CO?

A
  • highly toxic
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36
Q

Environmental consequences of C?

A
  • (soot)
  • causes global dimming
  • can cause respiratory problems
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37
Q

combustion of sulfur in alkanes?

A

sulfur-containing alkane fuels produce SO2 when burned.

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38
Q

Environmental consequences of SO2?

A
  • dissolve in atmospheric water and produce acid rain.

- acidic

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39
Q

Combustion of N2? and NO?

A
  • forms NO

- forms NO2

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40
Q

Environmental impact of NO?

A
  • toxic and can form smog.
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41
Q

Environmental impact of NO2?

A
  • toxic, acidic, and forms acid rain.
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42
Q

Environmental consequences of CO2?

A

contributes to global warming

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43
Q

Environmental consequences of unburnt hydrocarbons

A
  • contributes to formation of smog.
44
Q

Catalysts present in catalytic converters?

A
  • platinum
  • palladium
  • rhodium
  • coated on a ceramic honeycomb (large surface area).
45
Q

How do catalytic converters work?

A
  • CO is oxidised to form CO2.
  • unburned hydrocarbons are oxidised to form CO2 an H2O.
  • NO and CO react to form N2 and CO2.
    2NO + 2CO -> N2 + 2CO2
  • pollutants are removed by converting them into harmless gases.
46
Q

Why are fossil fuels oil non-renewable?

A

Fossil fuels reserves will eventually reserved. They are being used up faster than they can be replenished.

47
Q

What are alternative fuels?

A

They are fuels that have been derived from renewable resources.

48
Q

Examples of alternative fuels and their sources?

A
  • alcohols and biodiesel

- both derived from plants which is a renewable resource.

49
Q

How is are alcohols such as ethanol produced?

A

produced from the fermentation of sugars from plants.

50
Q

How is biodiesel produced?

A

Biodiesel is present in vegetable oils. Processing is not needed to be learned.

51
Q

advantages of biofuels?

A
  • reduction of use of fossil fuels (finite).
  • renewable.
  • more carbon-neutral
52
Q

disadvantages of biofuels?

A
  • less food crops may be grown.
  • more land may be used to not grow food crops.
  • deforestation to provide land.
  • shortage of fertile soils.
53
Q

What is a free radical?

A

a reactive species with an unpaired electron

54
Q

What is homolytic fission?

A

When a bond is broken and one electron goes to each atom to form two radicals.

55
Q

What is heterolytic fission?

A

When a bond is broken and both electrons goes to one atom to form ions.

56
Q

General formula for alkenes?

A

CnH2n

57
Q

unsaturated hydrocarbons? which ones?

A
  • alkenes?

- cycloalkenes

58
Q

What is in a c=c double bond?

A
  • alkenes have a c=c double bond.

- this double bond consists of 1 sigma and 1 pi bond.

59
Q
  • why are pi bonds vulnerable to attack by electrophiles?
A

pi bonds are exposed and have high electron density above and below the two nuclei.

60
Q

Why are pi bonds weaker than sigma bonds?

A
  • Electron density is above and below the two nuclei.

- electron density is further away from the nuclei.

61
Q

enthalpy of double bond

A

enthalpy for a c=c double bond is lower than the sum of the enthalpy for a sigma and pi bond.

62
Q

What is an electrophile?

A

an electron pair acceptor.

63
Q

Alkene to alkane?

A
  • hydrogenation
  • hydrogen H2(g)
  • nickel catalyst, heat
  • addition.
64
Q

alkenes to dihalogenoalkanes?

A
  • halogenation
  • halogen X2
  • room temperature
  • electrophilic addition
  • heterolytic fission
65
Q

alkene to halogenoalkene?

A
  • halogenation
  • Hydrogen halides HX (X=Cl, Br, I)
  • bubble gas through alkene at room temperature
  • electrophilic addition
  • heterolytic fission.
66
Q

If the alkene is unsymmetrical, addition of hydrogen bromide can lead to two isomeric products.

A

major product is formed via the more stable carbocation intermediate.

tertiary > secondary > primary

67
Q

Why are tertiary carbocation intermediates more stable than primary and secondary?

A
  • greater number of methyl groups surrounding the positive carbon.
  • the methyl groups are electron releasing and reduce the charge on the carbocation, stabilising it.
68
Q

alkene to diol?

A
  • oxidation
  • Potassium manganate (VII). KMnO4
  • in H2SO4 solution with water.
  • when reacted, MnO4- ions will turn purple to colourless
  • can be used for a test for alkene functional group.
69
Q

reaction of alkenes and bromine water?

A
  • BrOH
  • room temperature
  • addition
  • colour change from orange to colourless.
  • test for alkene functional group.
70
Q

Alkene to alcohol

A
  • hydration
  • steam H2O(g)
  • high temperature 300 to 600 degrees C
  • concentrated H3PO4.
71
Q

what are addition polymers formed from?

A

alkenes.

72
Q

Incineration (disposal of waste polymers)

A
  • rubbish is burnt and energy produced is used to generate electricity.
  • some toxins can be released
  • volume of rubbish will greatly reduce.
  • incinerator converts polymer waste into energy.
73
Q

recycling (disposal of waste polymers)

A
  • saves raw materials (polymers formed from compounds produced from crude oil). Recycling saves crude oil reserves.
  • polymers need collecting /sorting. Expensive in energy and manpower.
  • thermoplastic polymers can be melted and reshaped.
  • recycling involves converting polymer waste into other materials.
74
Q

Feedstock for cracking (disposal of waste polymers)

A

waste polymers can be cracked into gases. This produces a feedstock that can be used in other chemical reactions, often to make new polymers.

75
Q

How are waste products (caused by incineration of plastics) removed?

A
  • e.g HCl is reacted with a base/carbonate. The acidic HCl gas is neutralised to form a salt and water.
76
Q

development of biodegradable polymers.

A
  • biodegradable polymers can be broken down by microbes in the environment
77
Q

What is a primary halogenoalkane?

A

one alkyl group attached to the C atom bonded to the halogen atom.

78
Q

What is a secondary halogenoalkane?

A

two alkyl groups attached to the C atom bonded to the halogen atom.

79
Q

What is a tertiary halogenoalkane?

A

three alkyl groups attached the C atom bonded to the halogen atom.

80
Q

Which molecules match with which mechanism?

A
  • alkanes: free radical substitution
  • alkenes: electrophilic addition
  • halogenoalkanes: nucleophilic substitution
81
Q

what is a nucleophile?

A

an electron pair donor

82
Q

Halogenoalkane to alcohol?

A
  • nucleophilic substitution
  • warm H2O
  • alcohol and hydrogen halide formed
83
Q

Halogenoalkane to alcohol 2?

A
  • nucleophilic substitution
  • aqueous KOH (aq)
  • OH- acts as nucleophile
  • heat under reflux
  • alcohol and potassium halide formed.
84
Q

Halogenoalkane to alkene?

A
  • elimination reaction
  • ethanolic KOH
  • OH- acts as a base
  • alkene, potassium halide, water formed.
85
Q

Why is ethanolic KOH used for halogenoalkane to alkene?

A

to minimise water to prevent alcohol forming.

86
Q

Halogenoalkane to primary amine?

A
  • nucleophilic substitution
  • ammonia (NH3) in a sealed tube
  • ammonia acts as a nucleophile
  • primary amine, ammonium halide formed.
87
Q

Halogenoalkane to nitrile?

A
  • nucleophilic substitution
  • ethanolic potassium cyanide, heated under reflux
  • cyanide ion acts as a nucleophile
  • nitrile, potassium halide formed.
88
Q

in comparing rates of hydrolysis of halogenoalkanes, what solution is used?

A

silver nitrate solution.

89
Q

in comparing rates of hydrolysis of halogenoalkanes, why is ethanol used?

A

Ethanol acts as a co solvent for the halogenoalkane and the silver nitrate solution and ensures that the hydroxide ions can react with the halogenoalkanes.

90
Q

observations in in comparing rates of hydrolysis of halogenoalkanes? What precipitate is formed with the silver nitrate solution?

A

silver halide precipitate

  • chloroalkane: no precipitate (very slow)
  • bromoalkane: silver bromide, cream precipitate.
  • iodoalkane: silver iodide, yellow precipitate
91
Q

in comparing rates of hydrolysis of halogenoalkanes, which one has the fastest rate of hydrolysis and why?

A
  • iodoalkane
  • C-I bond is weakest with lowest bond enthalpy, so breaks most easily.
  • iodine is the most electronegative so the d+ on the carbon is the greatest. Therefore more prone to attack by nucleophile.
92
Q

in comparing rates of hydrolysis of halogenoalkanes, which one reacts the fastest? Primary, secondary, tertiary?

A
  • tertiary halogenoalkanes react the fastest.
93
Q

What are primary alcohols?

A

alcohols where 1 alkyl group is attached to the C bonded to the hydroxyl (OH) group.

94
Q

What are secondary alcohols?

A

alcohols where 2 alkyl groups are attached to the C bonded to the hydroxyl (OH) group.

95
Q

What are tertiary alcohols?

A

alcohols where 3 alkyl groups are attached to the C bonded to the hydroxyl (OH) group.

96
Q

Products of combustion of alcohols?

A

CO2 and H2O

- they burn with a clean flame.

97
Q

Alcohols + PCl5

A

chloroalkanes

  • chloroalkane, POCl3, HCl
98
Q

Alcohols + KBr + 50% conc H2SO4

A

bromoalkanes

  • the KBr and acid produces HBr
  • HBr reacts with alcohol to produce bromoalkane, water.
99
Q

Alcohols + red phosphorus + iodine

A

iodoalkanes

  • red phosphorus and iodine react to produce PI3.
  • PI3 reacts with alcohol to produce iodoalkane and phosphorus acid (H3PO3).
100
Q

What oxidising agent is used in the oxidation of primary and secondary alcohols?

A

potassium dichromate (VI) in dilute sulfuric acid solution

101
Q

What do primary alcohols oxidise to when heated under reflux?

A
  • aldehydes then carboxylic acids
102
Q

What do secondary alcohols oxidise to when heated under reflux?

A

ketones.

103
Q

Why can’t tertiary alcohols be oxidised?

A
  • due to a lack of hydrogen atoms bonded to the carbon with the OH group.
104
Q

How do you test for an aldehyde?

A
  • By using Fehling’s solution (containing blue Cu2+ ions)
  • heat gently
  • aldehydes oxidised into carboxylic acid and Cu2+ ions reduced to copper(I) oxide.
  • blue ions in solutions turns into red precipitate of Cu2O
  • ketones do not react.
  • can be used to distinguish between aldehydes and ketones.
105
Q

Alcohol + concentrated phosphoric acid?

A
  • heated with concentrated phosphoric acid
  • dehydration reaction
  • alkene, water molecule is formed
  • elimination reaction
  • heated
106
Q

How is a water molecule formed in the dehydration of alcohols?

A
  • OH is removed from the carbon and joined with an H from the adjacent carbon.
107
Q

Why can multiple products be formed in the dehydration of a secondary or tertiary alcohol?

A

The H removed from the adjacent carbon to the carbon with the OH group can be on either side of the carbon with the OH group. So, the C=C double bond can be formed on two sides.

Chemistry Year 12 (12 decks)

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