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Chemistry > Unit 4.1 - Stereoisomerism + start of 4.2 > Flashcards

Unit 4.1 - Stereoisomerism + start of 4.2 Flashcards

1
Q

Organic chemistry

A

The chemistry of carbon compounds, looking into the chemistry of different homologous groups

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2
Q

Homologous series

A

Groups of related compounds with the same functional group

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3
Q

What do members of a homologous series have in common?

A

The same functional group
The same general formula
Similar chemical properties
Gradually changing physical properties

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4
Q

Functional group

A

An element or group of elements that is responsible for the chemical properties of the compound (i.e - it provides a reactive site)

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5
Q

Alkane systematic name

A

-ane

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6
Q

Alkene systematic name

A

-ene

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7
Q

Halogenoalkane systematic name

A

chloro, bromo, iodophor

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8
Q

Primary alcohol functional group + systematic name

A

CH2OH
-1-ol

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9
Q

Secondary alcohol functional group + systematic name

A

CH(OH)
-2-ol

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10
Q

Aldehyde functional group and systematic name

A

CHO
-al

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11
Q

Ketone functional group and systematic name

A

-C=O-C-
-one

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12
Q

Carboxylic acid functional group and systematic name

A

-C=O-OH
-oic acid

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13
Q

Ester functional group and systematic name

A

-COOC-
-oate

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14
Q

Acid chloride functional group and systematic name

A

-COCl
-oyl chloride

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15
Q

Acid anhydride functional group and systematic name

A

(-CO)2O
-oic anhydride

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16
Q

Amide functional group and systematic name

A

-CONH2
-amide

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17
Q

Nitrile functional group and systematic name

A

-CN
-nitrile

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18
Q

Amine functional group and systematic name

A

-NH2
-amine

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19
Q

Amino acid functional group and systematic name

A

CN(NH2)COOH
——

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20
Q

Alkanes chemical reactions

A

Combustion
Cracking - homolytic fission of the C=C bond
Photo chlorination - free radical substitution

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21
Q

Alkenes chemical reactions (include any specific conditions required)

A

Catalytic hydrogenation (reduction) - nickel catalyst, production of margarine, 150C
Addition of bromine (electrophilic addition with halogen) - RT
Decolorisation of potassium manganate (VII)
Additional of water as steam - conc. H2SO4 or phosphoric acid, 300C, 60atm
Addition of hydrogen bromide - RT (propene = electrophyllic addition)
Addition polymerisation - 2000atm, 250C, O2 initiator

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22
Q

Preparation of alkenes

A

From halogenoalkanes using elimination reactions

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23
Q

Chemical reactions of halogenoalkanes

A

Nucleophillic substitution - reflux, distillation, aqueous sodium hydroxide
Elimination -reflux, ethanolic sodium hydroxide

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24
Q

Preparation of halogenoalkanes

A

Direct chlorination of alkanes - free radical substitution, UV light

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25
Q

Reactions of alcohols

A

Oxidation
-oxidising agent, acidified potassium dichromate, heated
Primary: alcohol —> aldehyde —> carboxylic acid
(Heat + distill) (reflux)
Secondary: alcohol —> ketone
(Reflux with acidified potassium dichromate)

Dehydration
Conc. H2SO4 in excess
170C
=alkene

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26
Q

Preparation of alcohols

A

From alkenes - electrophillic addition
H20 (steam)
300C
60atm pressure
Phosphoric acid

By fermentation, then distillation
35C
Zymase enzymes
Absence of air

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27
Q

Chemical reactions of carboxylic acids

A

Acid + base —> salt + water
Acid + metal —> salt + H2
Acid + carbonate —> salt + CO2 + H2O

Carboxylic acid + alcohol —><— ester + H2O
-conc. H2SO4
-heat + distillation

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28
Q

How is an amide prepared?

A

Carboxylic acid with ammonia

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29
Q

How is a nitrile prepared?

A

By dehydrating amides

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30
Q

How is an ester prepared?

A

Using carboxylic acids with alcohols

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31
Q

How are esters named?

A

1st part —> alcohol with name changed to end with -yo (carbons after COO group)
2nd part —> carboxylic acid or acid anhydride with name changed to end in -oate (carbons up to and including COO)

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32
Q

Primary alcohols

A

The carbon which carries the OH- group is only attached to 1 alkyl group (1 other carbon atom)

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33
Q

Secondary alcohols

A

The carbon which carries the OH- group is attached to 2 alkyl groups (which may be the same or different)

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34
Q

Test for alkenes

A

Bromine water is decolorised (orange —> colourless)
Potassium manganate (VII) (purple —> colourless)

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35
Q

Test for halogenoalkanes

A

1.) aqueous sodium hydroxide + heat to hydrolyse it
2.) neutralise the excess NaOH with dilute nitric acid (removes OH- ions that could interfere)
3.) aqueous silver nitrate

Chlorine - white ppt
Bromine - cream ppt
Iodine - yellow ppt

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36
Q

Test for alcohols

A

Acidified dichromate solution
Primary —> carboxylic acid
Secondary —> ketone
Tertiary —> no reaction

Orange —> green
(The dichromate (VI) ion is reduced to the chromium (III) ion)

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37
Q

Test for carboxylic acids

A

1.) addition of a metal carbonate/hydrogencarbonte
2.) effervescence forms - test this for CO2 (turns limewater milky)

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38
Q

Limewater

A

Calcium hydroxide

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39
Q

Compounds having carbon chains

A

Aliphatic compounds

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40
Q

What are the stages to naming organic compounds?

A
  1. The longest carbon chain is found
  2. The functional group is found
  3. Any side groups (radials) are found
  4. Assign a number to each carbon atom in the longest chain to find the position of functional groups or side groups. Do the numbering forwards and backwards and always use the lowest numbers possible.
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41
Q

7 C atom parent alkane

A

Heptane

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42
Q

Methane radical + formula

A

Methyl
CH3

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43
Q

Ethane radical and formula

A

Ethyl, CH3CH2

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44
Q

Propane radical and formula

A

Propyl, CH3CH2CH2

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45
Q

What are alkenes referred to as being since they C=C bonds?

A

Unsaturated

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46
Q

What is the feature that gives rise to E-Z isomerism?

A

C=C bond

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47
Q

Why do single bonds not lead to E-Z isomerism?

A

They can freely rotate = atoms in the bond are interchangeable

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48
Q

Why do double bonds lead to E-Z isomerism?

A

No free rotation

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49
Q

Why is there no free rotation in double bonds?

A

Due to the pi bond

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50
Q

E-Z isomers

A

Same molecular and structural formula but different spatial arrangement of atoms

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51
Q

E isomers

A

Atoms with the highest atomic masses on different sides of the double bond

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52
Q

Z isomers

A

Atoms with the highest atomic masses on the same side of the double bond

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53
Q

what does a COO group imply the presence of?

A

an ester

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54
Q

can amines be secondary?

A

yes

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55
Q

Stereo isomers definition

A

Stereo isomers have the same molecular and structural formulae but differ in the spatial arrangement of their atoms

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56
Q

How can steroisomerism be divided into groups?

A
  1. E-Z isomerism
  2. Optical isomerism
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57
Q

What is divided into E-Z and optical isomerism?

A

Steroisomerism

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58
Q

Explain what E-Z isomerism is

A

The absence of free rotation around the C=C bond in alkenes due to the presence of the pi bond can result in two different molecules which are E-Z isomers

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59
Q

Why is there no free rotation around the C=C bond in alkenes?

A

Due to the presence of the pi bond

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60
Q

What is a pi bond in an alkene caused by?

A

The sideways overlap of p-orbitals

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61
Q

How do we remember which is which with E-Z isomers?

A

z isomers —> “zame zide”

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62
Q

How do we work out the priority group with E-Z isomers?

A

We combine the atomic masses in order to work out the priority group. The priority group will have the biggest atomic masses.

63
Q

In which situation do we not have E-Z isomerism? What is required to ensure that there is?

A

If either atoms on both sides are the same then there’s no E-Z isomerism. We need 2 different groups attached to the carbon atoms making the double bond

64
Q

Name a molecule that exibits optical isomerism

A

Butan-2-ol

65
Q

Describe optical isomers

A

Have the same molecular and structural formulae but differ in the spatial arrangement of the atoms

66
Q

What do we call the isomers of, for example, butan-2-ol?

A

Optical isomers

67
Q

Why is butan-2-ol able to form optical isomers?

A

It has a chiral centre

68
Q

What is the thing that allows molecules to form optical isomers?

A

Having a chiral centre

69
Q

Chiral centre

A

A carbon atom which has four different atoms or groups attached to it

70
Q

A carbon atom which has four different atoms or groups attached to it

A

Chiral centre

71
Q

Give examples of chiral objects

A

Hands and gloves

72
Q

What type of molecules are the only ones to have optical isomers?

A

Chiral molecules

73
Q

Describe the two optical isomers of a molecule

A

Mirror images of each other
Are non-super imposable on one another

74
Q

Non-super imposable

A

Can distinguish them and if you place one on other, one will no longer be visible

75
Q

Name for a pair of optical isomers

A

Enantiomers

76
Q

Enantiomers

A

Pair of optical isomers

77
Q

Do optical isomers generally have the same physical properties?

A

Yes

78
Q

What is the physical property that optical isomers have that isn’t the same?

A

Their behaviour towards polarised light

79
Q

Plane polarised light

A

Light that only vibrates in a single plane

80
Q

How can we identify the different optimal isomers of enantiomers?

A

By analysing their behaviour towards plane polarised light

81
Q

How do enantiomers effect plane polarised light differently?

A

Will rotate it in opposite directions

82
Q

Racemic mixture

A

An aqueous solution that contains equimolar quantities of the enantiomers

83
Q

An aqueous solution that contains equimolar quantities of the enantiomers

A

Racemic mixture

84
Q

What does a racemic mixture do to plane polarised light and why?

A

Will not rotate it as the enantiomers will cancel out each other’s rotation

85
Q

What is light a form of?

A

Elecromagnetic radiation

86
Q

What type of waves does light consist of?

A

Transverse

87
Q

How is light seen when viewed at right angles to the direction of travel?

A

Is seen to vibrate in many planes

88
Q

When is light seen to vibrate in many planes?

A

When it is viewed at right angles to the direction of travel

89
Q

When are all vibrations except those in one plane for light removed?

A

If light is passed through a piece of Polaroid

90
Q

What happens if light is passed through a piece of Polaroid?

A

All vibrations except for those in one plane are removed

91
Q

What type of molecules are able to rotate the plane of polarised light?

A

Molecules with a chiral centre

92
Q

What are molecules with a chiral centre able to do?

A

Rotate the plane of polarised light

93
Q

What happens when a solution of a molecule containing a chiral centre has plane polarised light passed through it?

A

The plane of the light will be rotated

94
Q

Name for one optical light rotating light in a clockwise direction

A

Dextrorotatory

95
Q

Dextrorotatory

A

Rotating light in a clockwise direction

96
Q

Name for one optical light rotating light in an anti-clockwise direction

A

Laevorotatory

97
Q

Laevorotatory

A

Rotating in an anti-clockwise direction

98
Q

Right side of an optical isomer

A

Rectus

99
Q

Left side of an optical isomer

A

Sinister

100
Q

Why is it important to know about optical isomer?

A

Thalidomide was a drug taken by pregnant women to prevent nausea.
It wasn’t discovered until many had been taking it that some of its optical isomers caused birth defects whilst others didn’t
It resulted in severe birth defects in thousands of children

101
Q

Why can a racemic mixture be described as an equimolar mixture containing equal amounts of both enantiomers?

A

Because enantiomers have the same molecular formula and the same Mr. Therefore equal amounts will contain the same number of moles of each enantiomer

102
Q

Why are aromatic compounds called this?

A

The name comes from its smell

103
Q

What do aromatic compounds contain?

A

A benzene ring

104
Q

What type of compounds contain benzene rings?

A

Aromatic compounds

105
Q

Benzene formula

A

C6H6

106
Q

Where does benzene come from?

A

It’s a natural constituent of crude oil

107
Q

What are the risks of benzene?

A

It’s highly toxic and carcinogenic

108
Q

Aliphatic meaning

A

Straight chain

109
Q

What type of compounds that include benzene rings are named in a different way to aliphatic compounds?

A

Substituted aromatic compounds in which one or more of the hydrogen atoms on the benzene ring have been replaced by other elements or groups

110
Q

Are the structures of carbon and hydrogen atoms shown in Benzene’s structure? Why?

A

No, for the sake of brevity

111
Q

List all of the homologous series of the compounds in which the functional group is considered to be a substudent of the benzene ring

A

Hydrocarbons
Aromatic halogeno
Carboxylic acid
Nitro
Aliphatic halogeno
Aromatic aldehyde
Aromatic acid chloride

112
Q

Substuent

A

An atom or group that replaces another atom or group

113
Q

How are compounds in which the functional group is considered to be a substuent of the benzene ring named?

A

By prefixing or suffixing the word benzene with the name of the functional group

114
Q

Hydrocarbon homologous series (in an aromatic compound) functional group and systematic name

A

(No functional group)
-benzene

115
Q

Aromatic halogeno homologous series (in an aromatic compound) functional group and systematic name

A

-Cl, -Br, -I
-chloro etc

116
Q

Carboxylic acid homologous series (in an aromatic compound) functional group and systematic name

A

-COOH
-carboxylic acid

117
Q

Nitro homologous series (in an aromatic compound) functional group and systematic name

A

-NO2
-nitro

118
Q

Aliphatic halogeno homologous series (in an aromatic compound) functional group and systematic name

A

-Cl, -Br, -I
-chloroalkyl etc

119
Q

Give an example of an aliphatic halogeno to explain what is is

A

C6H5CH2Cl
1-chloromethyl-Benzene

120
Q

Where does the aliphatic carbon go in an aliphatic halogeno?

A

Between the benzene and the halogen

121
Q

How would you name this and what is it?
C6H5CHO

A

Benzene carbaldehyde or benaldehyde
It’s an aromatic aldehyde

122
Q

What does aromatic basically mean?

A

Has a benzene ring

123
Q

How would you name this and what is it?
C6H5COCl

A

Benzene Carbonyl Chloride / Benzoyl chloride

124
Q

Name all of the homologous series of the compounds in which the benzene ring, known as the phenyl group (C6H5-) is considered to be a substituent of the other group and the compound is named by prefixing the name of the substituent group with phenyl

A

Amine
Alkene
Ketone
Aliphatic alcohol

125
Q

What is the benzene ring also known as?

A

The phenyl group

126
Q

The phenyl group formula

A

C6H5-

127
Q

What do all of the following have in common?
Amine
Alkene
Ketone
Aliphatic alcohol

A

They’re homologous series of compounds in which the benzene ring, known as the phenyl group (C6H5-) is considered to be a substituent of the other group and the compound is named by prefixing the name of the substituent group with phenyl

128
Q

What do all of the following have in common?
Hydrocarbons
Aromatic halogeno
Carboxylic acid
Nitro
Aliphatic halogeno
Aromatic aldehyde
Aromatic acid chloride

A

They’re the homologous groups of compounds in which the functional group is considered to be a substuent of the benzene ring. The compound is named by prefixing or suffixing the word benzene with the name of the functional group.

129
Q

Amine homologous series (in aliphatic compounds) functional group and systematic name

A

-NH2
-amine

130
Q

Alkene homologous series (in aliphatic compounds) functional group and systematic name

A

-CH2=CH
-ene

131
Q

Ketone homologous series (in aliphatic compounds) functional group and systematic name

A

-C=O-R
-one

132
Q

Aliphatic alcohol homologous series (in aliphatic compounds) functional group and systematic name

A

-CH2OH
-ol

133
Q

Can ethanone exist?

A

No, but phenylethanone can

134
Q

Phenylethene alternative name

A

Styrene

135
Q

Styrene

A

Phenylethene

136
Q

Phenylamine other name

A

Aniline

137
Q

Aniline

A

Phenylamine

138
Q

Methyl benzene other name

A

Toluene

139
Q

Toluene

A

Methyl benzene

140
Q

Another word for benzene carboxylic acid

A

Benzoic acid

141
Q

Would an ester include benzene or phenyl in its name in an aliphatic compound?

A

Phenyl

142
Q

Give the homologous series, functional group and systematic name of compounds in which a trivial (old) name has been retained

A

Phenol
-OH
-phenol

143
Q

Another word for phenol

A

Hydroxybenzene

144
Q

What is phenol important for?

A

The synthesis of drugs e.g: paracetamol and aspirin

145
Q

Which benzene is important for the synthesis of drugs such as paracetamol and aspirin?

A

Phenol

146
Q

How do we name an aliphatic compound when there is more than one substituent on the benzene ring?

A

The ring is numbered so that one group is at position 1 and the other is numbered with reference to this group

147
Q

When are the numbers 5 and 6 used in the naming of a benzene ring?

A

When 2 and 3 are already in use

148
Q

Which positions are the same on a benzene no?

A

2 and 6
3 and 5

149
Q

What does TCP stand for and what is it used in?

A

Trichloro phenol
Disinfectants

150
Q

During the electrophilic addition reaction of bromine with a halogen, what forms?

A

Major and minor products

151
Q

What is the major product formed from when major and minor products can form? Why?

A

Major product formed from the secondary carbocation
Secondary carbocation is more stable than the primary one

152
Q

Secondary carbocation

A

Positive charge attached to a carbon atom attached to 2 carbon atoms

153
Q

Conditions for free radical substitution

A

UV light

154
Q

Structural isomerism vs stereoisomerism

A

Structural isomerism: concerned with the position of atoms in a molecule
Stereoisomerism: concerned with the position atoms take up in space

Chemistry (39 decks)

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