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chemistry > module 4.1- core organic > Flashcards

module 4.1- core organic Flashcards

1
Q

define organic chemistry

A

study of the structure, properties, composition, reactions and preparation of carbon-containing compounds

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2
Q

why is carbon so special?

A

in group 4, each carbon can form four covalent bonds to other atoms, can form long chains with triple or double bonds

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3
Q

define saturated (in terms of hydrocarbons)

A

contains only single bonds, fully saturated carbons

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4
Q

are alkenes saturated or unsaturated?

A

unsaturated as they contain a carbon-carbon double bond

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5
Q

define homologous series

A

a family of compounds with similar chemical properties whose SUCCESSIVE members differ by the addition of a -CH2- group

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6
Q

define functional group

A

the part of the organic molecule that is largely responsible for the molecule’s chemical properties.

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7
Q

what are the three classes of hydrocarbons

A

aliphatic - carbon atoms joined to each other in unbranched (straight) or branched chains, or non-aromatic rings

alicyclic - carbon atoms are joined to each other in a ring (cyclic) structure, with or without branches

aromatic - some or all of the carbons are found in a benzene ring

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8
Q

what does the stem, prefix and suffix indicate about hydrocarbons

A

stem - indicates the number of carbon atoms in the longest continuous chain of the molecule

prefix - indicates the presence of side chains or functional groups

suffix - indicates functional groups

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9
Q

what are the three homologous series of aliphatic hydrocarbons that you need to know

A

alkanes - single carbon-to-carbon bonds
alkenes - double carbon-to-carbon bonds
alkynes - triple carbon-to-carbon bonds

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10
Q

how do you name aliphatic alkanes
(4steps)

A
  1. all alkanes have the suffix -ane
  2. identify the longest continuous chain of carbon atoms and name it
  3. identify side chains attached to “parent chain”. the name of the alkyl group is added as a prefix to the name of the parent chain
  4. add numbers before any alkyl groups to show the position of the alkyl groups on the parent chain
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11
Q

how do you name alicyclic alkanes ?

A

same as aliphatic alkanes but add the prefix cyclo- to show carbon atoms are arranged in a ring structure

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12
Q

what is the functional group and suffix of an aldehyde

A

-CHO (oxygen double bonded to carbon)
suffix= -al

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13
Q

what is the functional group and suffix of a ketone

A

-C(CO)C- (co double bond)
suffix = -one

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14
Q

what is the functional group and suffix of an ester

A

-cooc- (first oxygen double bonded)
-oate = suffix

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15
Q

what is the functional group and suffix of an acyl chloride

A

-COCl (carbon and oxygen double bonded)
suffix = -oyl chloride

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16
Q

what is the functional group and prefix AND suffix of an amine

A

-NH2
prefix= amino-
suffix= -amine

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17
Q

what is the functional group and suffix of a nitrile

A

-CN (triple bond)
suffix = -nitrile

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18
Q

how do you write the skeletal formula

A

a line represents a single bond
an intersection of two lines represents a carbon atom
the end of a line represents a CH3 group

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19
Q

define nomenclature

A

the system used for naming organic compounds

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20
Q

what is the difference between molecular and empirical formula

A

empirical is the simplest whole number ratio of atoms whereas molecular is the actual number of atoms of different elements in a molecule

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21
Q

what does displayed formula mean

A

shows every atom and every bond in a molecule

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22
Q

give the suffixes for:
1. no double bonds
2. at least 1 double bond
3. an alcohol
4. an aldehyde
5. a ketone
6 a carboxylic acid

A
  1. -ane
  2. -ene
  3. -ol
  4. -al
  5. -one
  6. oic acid
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23
Q

define structural isomerism

A

when molecules have the same molecular formula but different structural formula

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24
Q

what are the 3 types of structural isomerism

A

chain - different chain length caused by branching

positional - position of the functional group changes

functional group - composition of the compound can change the functional group

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25
Q

what are the 3 functional group isomers of C3H8O

A

propan-1-ol
propan-2-ol
methoxethane - ether - 2 carbonds bonded directly to oxygen (COC) not (COH)

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26
Q

how can isomers change the physical properties of a compound

A

Different intermolecular forces between molecules can lead to differences in
boiling/melting points, viscosities, solubilities, densities etc.

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27
Q

how can isomers change the chemical properties of a compound

A

Different functional groups can have different interactions with biological systems
(toxicity), reactivity, bond enthalpy, flammability, oxidation states etc.

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28
Q

what makes alkanes saturated

A

only contains single sigma bonds

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29
Q

what is a sigma bond

A

a strong covalent bond formed by overlap of atomic orbitals along the bond axis (i.e. on the line connected by the 2 bonded atoms)

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30
Q

what does having a sigma bond mean for the atoms mobility

A

atoms can rotate freely around a sigma bond and molecule shapes are not rigid.

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31
Q

what is the shape of alkanes and why is it like this?

A

tetrahedral 109.4 degree bond angle

because each carbon is surrounded by 4 electron pairs in four sigma bonds. the repulsion of these electron pairs results in the 3D tetrahedral arrangement around each carbon atom

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32
Q

what is the order of priority in nomenclature for the function groups
highest - lowest

and their suffix/ prefix

A

carboxylic acid -oic acid
ester -oate
amide -amide
nitrile -nitrile
aldehyde -al
ketone -one
alcohol -ol or hydroxy-
amine -amine or amino-
alkene -ene
alkyne -yne
alkane -ane
ether alkoxy-
alkyl halide halo-

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33
Q

what are the two types of bond fission?

A

homolytic fission - each of the bonded atoms takes one of the electrons from the covalent bond

heterolytic fission - one of the atoms takes both electrons from the covalent bond resulting in a negative and positive ion

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34
Q

what do reaction mechanisms tell you?

A

HOW the reaction takes place

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35
Q

what do curly arrows in reaction mechanisms tell you

A

show the movement of the electron pairs when bonds are broken or made

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36
Q

what is a radical

A

an atom or group of atoms with an unpaired electron

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37
Q

how do curly arrows represent homolytic fission

A

as one electron goes to each atom, a “fish hook” arrow goes opposite ways using half an arrow head at each end to show two electrons moving

38
Q

what are an atom or group of atoms with an unpaired electron called

A

a radical

39
Q

what are the three types of reaction mechanisms

A

addition - two reactions form one product

substitution - an atom, or group of atoms, is replaced by a different atom or group of atoms

elimination - removal of a small molecule from a larger one. one reactant forms two products

40
Q

what is the difference between a nitrile, an amine and an amide

A

nitrile is nitrogen triple bonded to carbon
amine = NH2
amide = oxygen double bonded to carbon, carbon bonded to NH2

41
Q

in nomenclature, how do you order the haloalkane functional groups if there are more than one
eg. bromo, fluoro, iodo

A

alphabetically
bromo, chloro, fluoro, iodo

42
Q

what two things affect the boiling points of alkanes and how?

A
  1. number of carbons in the chain - increases - more points of contact/ greater surface area, increases london dispersion forces
  2. branches - decrease - unable to pack tightly together so reducing points of contact.
43
Q

which has a greater effect on the boiling point of alkanes - number of carbons or branches

A

number of carbons

44
Q

why are alkanes non-polar

A

the difference in electronegativity between carbon and hydrogen is very small and alkanes have a symmetrical tetrahedral shape so no polar bonds

45
Q

what colour are the flames of
a. complete
b. incomplete
combustion of alkanes

A

complete = blue flame
incomplete = orange flame

46
Q

what are the limitations of radical substitution?

A

radicals are very reactive, therefore:
- multi-substitution can occur, lots of termination steps
- limited control over reaction - unwanted waste products form
- no control over what point on the C chain where the reaction occurs
- can produce longer alkanes - have to be separated
-waste products from side reactions

47
Q

what is the colour of ethanoic acid in
1. litmus indicator
2. universal indicator

A
  1. light red
  2. orange
48
Q

what is the colour of hydrochloric acid in
1. litmus indicator
2. universal

A
  1. dark red
  2. red
49
Q

what observations from ethanoic acid with:
1. magnesium
2. sodium carbonate

A
  1. slight fizzing
  2. less CO2 produced - slow reaction
50
Q

what observations from hydrochloric acid with:
1. magnesium
2. sodium carbonate

A
  1. rapid fizzing
  2. fast reaction - lots of CO2 gas produced
51
Q

what bonds are present in alkanes

A

LDFs and Instantaneous dipole interactions

52
Q

true or false “incomplete combustion is more likely with a shorter chain”

A

false - more likely with a longer chain

53
Q

what bonds make up a C=C bond?

A

one sigma bond on the bond axis and one Pi bond above and below the carbons

54
Q

what is the reactivity of alkanes like?

A

very low reactivity due to sigma bonds having:
low polarity
high bond enthalpy - energy required to break the bonds

55
Q

what properties increase and decrease as size of alkanes increase

A

boiling point increases
volatility (how easily to turn to gas) decreases
viscosity (how easily it flows) - increases
flammability - decreases

56
Q

how are balanced combustion equations of alkanes given?

A

the fuel is one mole and the oxygen is given as halves

57
Q

explain why nitrogen is often produced in the combustion of alkanes in cars and engines

A

due to the high temperatures, the nitrogen reacts with the oxygen in the atmosphere, forming nitrogen oxides

58
Q

explain why straight chain isomers have higher boiling points than their branched chain isomers

A

straight chains can pack together more tightly, therefore have more points of contact/ greater surface area. increasing the strength of the london dispersion forces, requiring more energy to break the bonds

59
Q

what are the three stages of radical chain reactions
(explain them)

A
  1. initiation - creates the radical species
  2. propagation - radicals react with stable molecules to displace an atom and form new radicals (substitution)
  3. termination - two free radicals react to form a stable adduct.
60
Q

write an equation for the initiation stage of the reaction of chlorine with C4H10
what form of fission is this?
what are the conditions necessary?

A

Cl-Cl –> 2Cl ‘ - represents 2 radicals (unpaired electrons)

homolytic fission - one electron goes to each atom

conditions - UV

61
Q

write an equation to show the propagation stages of the reaction of C4H10 + Chlorine (2 equations)

A

C4H10 + Cl’ –> C4H9’ + HCl

C4H9’ + Cl2 –> C4H9Cl + Cl’ (where ‘ represents radicals - lone electrons)

62
Q

what shape forms around the double bonded carbon atoms in alkenes and what is the bond angle of the surrounding atoms

A

trigonal planar - 120degrees

63
Q

what determines the shape around the double bonded carbons in alkenes

A

there are 3 regions of electron density around each carbon atom
the regions repel each other as far as possible,
all atoms are in the same plane

64
Q

describe how the double carbon bond is formed in alkenes

A

3 electrons from the carbon are bonded to other atoms via sigma bonds. leaving one electron, in a p-orbital, then a Pi bond is formed.
Pi bonds are formed by the sideways overlap of the 2 p-orbitals, one from each carbon atom in the double bond. The Pi electron density is concentrated above and below the sigma bond joining the nuclei of the carbon atoms.

65
Q

what are the properties of alkenes

A

insoluble in water - non-polar

boiling points increase with chain length - more points of contact = increased london dispersion forces

lower b.p. than equivalent alkane - lower Mr so fewer electrons and fewer london dispersion forces. alkenes don’t pack together as tightly due to both 109.5 and 120 degree bond angles.

66
Q

define stereoisomerism

A

when molecules have the same structural formula but a different arrangement of the atoms in space

67
Q

when does a molecule have E/Z isomerism

A

if it has:
a c=c double bond
and different groups attached to each carbon in the double bond.

68
Q

what is the difference between E and Z isomers

A

E isomers have the 2 hydrogens at diagonally opposite sides of the two carbons, same for the other groups.

Z isomers have the hydrogens on the same side of the carbon double bond - either lower side or upper side

69
Q

what is the difference between E/Z isomerism and Cis-Trans isomerism

A

Cis-Trans have to have same properties as E/Z but one of the attached groups on each carbon atom must be the same on each side

70
Q

what is the Cahn-Ingold-Prelog nomenclature

A

atoms attached to the carbon bond are given priority based on their atomic number.
if both higher priority are on the same side = Z isomer
if higher priority are diagonally opposite = E isomer

71
Q

what are the three chemical tests for alkenes

A

combustion - more sooty yellow flame due to higher percentage mass of carbon
decolourises bromine water from orange (shows unsaturation, can also be an alkyne)
oxidation - decolourises potassium manganate (acidified)

72
Q

what type of fission occurs in electrophilic addition?

A

heterolytic fission (both electrons go to one element, forming 2 ions

73
Q

in electrophilic addition, what initiates heterolytic fission in the covalent bonded addition molecule?

A

the Pi bond creates a region of high electron density above and below the molecule, inducing a dipole in the covalent bond

74
Q

what is the common misconception of the Pi bond?

A

that the Pi bond is the double bond

actually the Pi bond forms as well as the sigma bond, creating a double bond

75
Q

why are alkenes more reactive than alkanes

A

the Pi bond has a lower bond enthalpy so requires less energy to break.
the position of the Pi bond (above and below carbons) makes it easier to “attack” the electron pair

76
Q

what reactions do all alkenes undergo?

A

electrophilic addition reactions

77
Q

define electrophile?

A

electron pair acceptor - often positive ions or have a delta positive charge (electron deficient)

78
Q

what are the reaction conditions for hydrogenation of an alkene
what is the product

A

reagent - Hydrogen (H2)
conditions - 150 degrees C, Nickel catalyst
product - alkane

79
Q

what are the conditions for the bromination of alkenes
what is the product

A

reagent - Br2
conditions - N/A, mix at room temp
product - dibromoalkanes

80
Q

what are the conditions for the reactions of alkenes and hydrogen halides?
what is the product?

A

reagent - HBr
conditions = N/A, mix at room temp
product - bromoalkane

81
Q

what are the conditions for the hydration of alkenes
what is the product?

A

reagent - water (steam)
conditions - 300degrees C, 6MPa (60atm), H3PO4/H2SO4 catalyst
product - alcohol

82
Q

why are most addition polymers not biodegradable?

A

because they contain no polar bonds and are therefore unreactive

83
Q

why are polyesters and polyamides biodegradable?

A

because they are reactive due to weak polar bonds in the polymer chain

84
Q

define biodegradability

A

the ability of a substance to be broken down physically and/or chemically by microorganisms

85
Q

in biodegradation, what are the products of acidic hydrolysis and basic hydrolysis

A

acidic - original monomers produced
basic - salt of the dicarboxylic acid monomer produced

86
Q

define photodegradability

A

when substances are broken down chemically using wavelengths similar to light (UV is most effective)

87
Q

what are the pros and cons of biodegrading?

A

pros: reduces build up of landfill, cheap - no human interference required, monomers can be reused for other applications

cons: takes a long time, doesn’t fully break down. if a substance is biodegradable, it will have to be replaced meaning more pollution in the production of a replacement

88
Q

what are the pros and cons of feedstock

A

pros: works with unwashed and unsorted polymers, 30-40 commercial technologies available to assist the method, recovers raw materials and primary energy from waste

cons: industrial installations are rare - poor profitability, high investment cost, frequent cleaning and maintenance, cost of catalysts etc.

89
Q

what are the pros and cons of landfill

A

pros: contained in a specific location =, biodegradable polymers will slowly degrade
cons: limited land available, slow degradation, leaching of toxic compounds, gas emissions released (methane)

90
Q

what are the pros and cons of incineration

A

pros: energy released can be used as electricity, takes up less space than landfill, prevents build-up on land

cons: toxic gases and particulates released, increased in CO2 emissions, expensive, big factories require lots of polymer building materials, people complain due to “eye sore” - sight pollution

91
Q

what are the pros and cons of recycling

A

pros: reuse and conservation of finite hydrocarbons, less toxic gas released, reduction of landfill (eyesore), can also save people money eg. DIY upcycling
cons: collection, sorting and remoulding requires energy, expensive and time consuming.

chemistry (9 decks)

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