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Organic Chemistry Flashcards

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1
Q

what does nomenclature mean?

A

The system used for naming organic compounds

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2
Q

What does the term empirical formula mean?

A

Simplest whole number ratio of atoms in a molecule

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3
Q

What does the term displayed formula mean?

A

It shows every atom and every bond in a molecule

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4
Q

What does the term structural formula mean?

A

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

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5
Q

Define skeletal formula

A

A type of formula which is drawn as lines 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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6
Q

Define 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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7
Q

What is a functional group?

A

A group of atoms responsible for characteristic reactions of a compound

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8
Q

Give the suffixes for:
- No double bonds
- At least one double bond
- An alcohol
- An Aldehyde
- A ketone
- A carboxylic acid

A
  • No double bonds (-ane)
  • At least one double bond (- ene)
  • An alcohol (-ol)
  • An aldehyde (-al)
  • A ketone (-one)
  • A carboxylic acid (-oic acid)
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9
Q

Give the prefixes for:
- CH3 group
- C2H5 group
- C3H7 group
- C4H9 group
- Cl group
- Br group
- I group

A
  • CH3 group ( Methyl -)
  • C2H5 group (ethyl -)
  • C3H7 group ( Propyl-)
  • C4H9 group (butyl-)
  • Cl group (chloro-)
  • Br group (bromo-)
  • I group (iodo-)
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10
Q

What is the general formula of alkanes?

A

CnH2n+2

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11
Q

What is the general formula for alkenes?

A

CnH2n

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12
Q

What does saturated mean?

A

Organic compounds which only contain single bonds

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13
Q

What are unsaturated compounds?

A

Organic compounds that contain at least one carbon-carbon double covalent bond

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14
Q

Define structural isomerism

A

When molecules have the same molecular formula but different structural formula

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15
Q

What are the 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

What are 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

E-Z isomerism is caused by the limited rotation about carbon to carbon double bonds
If the two substituents with the highest molecular mass are on the same side of t he double bond, it is the Z (Zusammen) isomer
if they are on different sides, it is the E ( Entgegen) isomer

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18
Q

What is Cis-tans isomerism?

A

Special type of E/Z isomerism where the two substituents on each carbon atom are the same

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19
Q

What is homolytic fission?

A

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

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20
Q

What is 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

The radicals collide and the electrons are involved in the bond formation

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23
Q

What is an alkane?

A

A saturated hydrocarbon containing C-H bonds only

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24
Q

How are alkane fuels obtained?

A

Alkane fuels are obtained from the fractional distillation, cracking and reforming crude oil`

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25
Q

Describe the process of fractional distillation

A
  1. The oil is pre-heated then passed into a column
  2. The fractions condense at different heights and the temperature of column decreases upwards
  3. The separation of the fuels depends on boiling point which depends on size of molecules. The larger the molecule the larger the London forces
  4. Similar molecules( size, bp, mass) condense together and so are collected at the same fraction
  5. Small molecules condense at the top at lower temperatures and big molecules condense at the bottom at higher temperatures
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26
Q

What is cracking?

A

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

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27
Q

What is the reforming of crude oil?

A

It is the processing of straight-chain hydrocarbons into branched-chain alkanes and cyclic hydrocarbons for efficient combustion

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28
Q

What is the shape and angle of alkane?

A

Tetrahedral
109.5 degrees

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29
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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30
Q

How reactive are alkanes?

A

Very unreactive

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31
Q

What reactions will alkanes undergo?

A

Combustion and reaction with halogens

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32
Q

What type of reaction is combustion?

A

Oxidation reaction

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33
Q

What is complete combustion?

A

combustion that occurs with plentiful supply of air

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34
Q

Write an equation for the complete combustion of octane

A

C8H18 (g) + 12.5 O2 (g) -> 8CO2 (g) + 9H2O (l)

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35
Q

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

A

Carbon dioxide and water

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36
Q

What is the color of the Bunsen burner flame during complete combustion?

A

Blue flame

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37
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 dioxide
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38
Q

Write an equation for the complete combustion of propane

A

C3H8 + 5 O2 –> 3 CO2 + 4H2O

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39
Q

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

A

Longer chains

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40
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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41
Q

What is the environmental impact of carbon monoxide?

A

It is toxic/ poisonous

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42
Q

What is the environmental impact of soot (carbon)?

A

Asthma, cancer, global dimming

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43
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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44
Q

What are the environmental impacts of unbranched hydrocarbons?

A

They contribute towards formation of smog

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45
Q

What is the importance of a catalytic converter?

A

These remove CO, nitrogen and unburned hydrocarbons
(e.g Octane, C8H18) from the exhaust gases turning them into less toxic products CO2, N2 and H2O

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46
Q

What are biofuels?

A

They are fuels developed from renewable resources. Alcohols and biodiesel are examples of renewable plant-based fuels

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47
Q

What are the advantages and disadvantages of biofuels?

A

Advantages
- Reduces use of non-renewable fossil fuels
- Use of biodiesel is more carbon-neutral
- Fossil fuels can be used as feedstock for organic compounds
- Less large scale pollution
Disadvantages
- Less food crops may be grown because crops for biofuels would be grown instead
- Reduction of rain forest that have to be cut down to provide land
- Shortage of fertile soils

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48
Q

How are halogenoalkanes formed from alkanes?

A

radical substitution

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49
Q

In the presence of what does alkane react with halogens?

A

UV light

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50
Q

What are the three stages of free radical substitution?

A
  • initiation - breaking halogen bond to form free radicals
  • Propagation - Chain part of reaction where prods are formed but free radical remains
  • Termination - Free radicals removed, stable products formed
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51
Q

Write equations for the reaction of CH4 with Cl2 to form CH3Cl

A

Initiation: Cl2 –> 2Cl. (In presence of UV light)
Propagation: Cl. + CH4 –> HCl + . CH3 then
. CH3 + Cl2 –> CH3Cl + Cl.
Termination:
.CH3 + Cl. –> CH3Cl
2Cl. –> Cl2
. CH3 + .CH3 –>CH3CH3

52
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

53
Q

What are alkenes?

A

unsaturated hydrocarbons that contain at least one Carbon to carbon double bond may up of a pi bond and a sigma bond

54
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

55
Q

What bond restricts the rotation of carbon atoms?

A

Pi bond

56
Q

What is the angle and shape of a double bond?

A

Trigonal planar
120 degrees

57
Q

What is the qualitative test for alkanes?

A

This tests for Carbon to carbon double bond using bromine water. If the alkane is present bromine water decolorizes

58
Q

Are they more or less reactive than alkanes? Why?

A

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

59
Q

What intermolecular forces of attraction do they have?

A

only London forces due to non-polar bonds

60
Q

Write an equation for the complete combustion of pent-3-ene

A

CH3CHCHCH2CH3 + 7.5 O2 –> 5O2 + 5H2O

61
Q

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

A

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

62
Q

What is an electrophile?

A

Species that are electron pair acceptors

63
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

64
Q

Major products will be formed from which kinds of carbocations?

A

Tertiary (or the most stable available)

65
Q

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

A
  • Stem in the presence of an acid catalyst, usually phosphoric acid
  • Reaction is called hydration
66
Q

What are the products of the hydration reaction?

A

An alcohol

67
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

68
Q

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

A

Halogenation

69
Q

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

A

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

70
Q

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

A

-Alkene + Hydrogen = Alkane
- Hydrogenation
- Conditions –> 150 degrees celsius, nickel catalyst

71
Q

What is an addition polymer?

A

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

72
Q

What are monomers? What form do they usually take?

A
  • Molecules which combine to form a polymer
  • Usually have a carbon to carbon double bond which breaks to leave a repeating pattern
73
Q

What are the ways in which plastics can be disposed? (6)

A
  • Landfill
  • Combustion
  • Electricity generation
  • Reuse
  • Recycle
  • Organic feedstock
74
Q

what are the disadvantages of recycling?

A
  • plastics must be sorted into different types
  • Expensive
  • Labor intensive
  • Requires high technology
75
Q

How can chemists limit the problems caused by polymer disposal?

A
  • Developing biodegradable polymers
  • Removing toxic waster gases caused by incineration of plastics
76
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 to produce plastics and in other industries

77
Q

What are halogenoalkanes?

A

Saturated organic compounds that contain carbon atoms and at least one halogen atom

78
Q

Are halogenoalkanes soluble in water?

A

Insoluble as C-H bonds are non-polar, not compensated for enough by C-X bond polarity

79
Q

Do halogenoalkanes have a polar bond? Why?

A

Yes polar, as halogen has a higher electronegativity than C ( halogen has a negative dipole, carbon has a positive dipole)

80
Q

What type of intermolecular forces do halogenoalkanes have? Why?

A

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

81
Q

When would they have higher boiling points?

A
  • increase carbon chain length
  • Halogen further down group 7
82
Q

How would the mass of a halogenoalkane compare with the mass of an alkane of the same chain length?

A

Greater as mass of halogen is greater than mass of H

83
Q

What is the most important factor in determining halogen reactivity?

A

The strength of carbon halogen bond

84
Q

What would bond polarity suggest the order of reactivity would be?

A

C-F would be most reactive as most polar bonds

85
Q

What would bond enthalpies suggest the order of reactivity would be?

A

C-l would be most reactive as lowest bond enthalpy

86
Q

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

A
  • The tertiary halide produces a precipitate almost instantly.
  • The secondary halide gives a slight precipitate after a few seconds
  • The primary halide takes considerably longer to produce a precipitate
87
Q

Define a nucleophile

A

Electron pair donor

88
Q

Give three examples of nucleophiles

A

: OH-
: CN-
: NH3

89
Q

what is nucleophilic substitution?

A

A reaction where a nucleophile donates a lone pair of electrons to a positive dipole carbon atom, negative dipole atom leaves molecule (replaced by nucleophiles)

90
Q

What is hydrolysis?

A

A reaction where water is a reactant

91
Q

what reactant often produces hydroxide ions for hydrolysis?

A

water

92
Q

What fission does water undergo to produce OH-?

A

Heterolytic fission

93
Q

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

A
  • NaOH or KOH dissolved in ethanol (no water present)
  • Heated
94
Q

What is formed in the elimination reaction of haloalkanes?

A

An alkane, water and hydrogen ion

95
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
96
Q

How do you convert halogenoalkane into alkene?

A

use of ethanoic potassium hydroxide to produce alkenes ( Where the hydroxide ion acts as a base)

97
Q

How do you produce nitriles from haloalkanes?

A

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

98
Q

How can you compare the rate of hydrolysis of haloalkanes?

A

Acqueous silver nitrate is added to a halogenoalkane and a silver halide precipitation is formed. The quicker the precipitate is formed the faster the rate of hydrolysis.

  1. AgI(s) - yellow precipitate
  2. AgBr(s) - cream precipitate
  3. AgCl (s) - White precipitate

forms faster in order of 3,2,1

99
Q

What is the functional group of alcohol?

A

hydroxyl group - OH

100
Q

What is the general formula of an alcohol?

A

CnH2n+1 OH

101
Q

How do you name alcohols (one prefix, one suffix)?

A

Hydroxyl -OR -ol

102
Q

What kind of intermolecular forces do alcohol have? Why?

A

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

103
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

104
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
105
Q

What makes an alcohol primary?

A

C bonded to OH is only bonded to one other C atom

106
Q

What makes an alcohol secondary?

A

C bonded to OH is bonded to two other C atoms

107
Q

What makes an alcohol tertiary?

A

C bonded to OH is bonded to three other C atoms

108
Q

Write an equation for the combustion of ethanol

A

C2H5OH (l) + 3O2 (g) –> 2CO2 (g) + 3H2O (l)

109
Q

What forms if you partially oxidize a primary alcohol?

A

An aldehyde

110
Q

What conditions are needed to partially oxidize a primary alcohol?

A
  • Dilute sulfuric acid
  • potassium dichromate (VI)
  • Distill product as it’s produced
  • Gentle heating
111
Q

Write an equation for the partial oxidation of ethanol

A

CH3 CH2 OH (l) + [O] –> CH3CHO (g) + H2O (l)

112
Q

What forms if you fully oxidize a primary alcohol?

A

A carboxylic acid

113
Q

What conditions are needed to fully oxidize a primary alcohol?

A
  • Concentrated sulfuric acid
  • potassium dichromate (VI)
  • Reflux
  • Strong heating
114
Q

Write an equation for the full oxidation of ethanol

A

CH3 CH2 OH (l) + 2[O] -> CH2COOH (g) + H2O (l)

115
Q

What forms if you oxidize a secondary alcohol?

A

A ketone

116
Q

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

A
  • Concentrated sulfuric acid
  • Potassium dichromate (VI)
  • Strong heating
117
Q

Write an equation for the oxidation of propan-2-ol

A
118
Q

is it possible to oxidize tertiary alcohol?

A

No

119
Q

What is a dehydration reaction?

A

A reaction where water is lost to form an organic compound

120
Q

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

A
  • Alkene and water
  • Concentrated sulfuric acid or concentrated phosphoric acid and 170 degrees celsius
121
Q

How can you produce chloroalkanes from alcohols?

A
  • Use PCl5 ( PCl 3/ conc HCl / SOCl2 / mixture of NaCl+ H2SO4 can also be used for substituting a Cl)
  • E.g. CH2CH2 OH + PCl5 –> CH3 CH2 Cl + POCl3 + HCl
122
Q

How can you produce bromoalkanes from alcohols?

A

Use 50% concentrated sulfuric acid and potassium bromide

123
Q

How can you produce iodoalkanes from alcohols?

A
  • Use red phosphorus and iodine
  • Pl3 + 3CH3CH2 OH –> 3CH2 CH2 l + H2PO3
124
Q

How do you prepare and purify a liquid organic compound?

A
  1. Heat under reflux
  2. Extract with a solvent in a separating funnel
  3. Distill
  4. Dry with an anhydrous salt
  5. Determine boiling temperature
125
Q
A

CHEMISTRY (11 decks)

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