Organics Week 4 Flashcards

1
Q

What is meant by dextrorotatory?

A

Dextrorotatory refers to the ability of an enantiomer to rotate plane-polarised light in a clockwise direction (+).

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2
Q

What is a racemate?

A

A racemate, also known as a racemic mixture, is a mixture that contains equal amounts of both enantiomers. It does not have the ability to rotate plane-polarised light.

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3
Q

What is optical isomerism?

A

Optical isomerism is a type of stereoisomerism in chemistry where compounds have the same structural formula but differ in the spatial arrangement of atoms, resulting in mirror-image isomers called enantiomers.

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4
Q

What are enantiomers?

A

Enantiomers are mirror-image isomers that cannot be superimposed on each other. They have the same structural formula but differ in their spatial arrangement of atoms.

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5
Q

What is a chiral carbon atom?

A

A chiral carbon atom is a carbon atom that is bonded to four different groups, resulting in a tetrahedral arrangement of these groups around the carbon.

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6
Q

What is laevorotatory?

A

Laevorotatory refers to the ability of an enantiomer to rotate plane-polarized light in an anticlockwise direction (-).

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7
Q

How do optical isomers differ in their properties?

A

They have similar physical and chemical properties but differ in their ability to rotate plane-polarised light.

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8
Q

What are the different types of isomerism?

A

There are different types of isomerism, including chain isomerism, position isomerism, and functional group isomerism.

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9
Q

What are the different effects of thalidomide depending on the enantiomer?

A

For example, thalidomide has different effects depending on the enantiomer, with one causing birth defects and the other having sedative properties.

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10
Q

What are optical isomers also known as?

A

Optical isomers, also known as enantiomers, are mirror images of each other and cannot be superimposed.

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11
Q

What is a racemic mixture?

A

A racemic mixture is formed when equal amounts of both enantiomers are present and it does not rotate plane-polarized light.

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12
Q

How can the stereochemistry of a molecule influence its drug action?

A

Different optical isomers can have distinct effects. For instance, one enantiomer of thalidomide causes birth defects, while the other has sedative properties.

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13
Q

How can chemical reactions lead to the formation of racemates?

A

Chemical reactions can lead to the formation of racemates, such as when unsymmetrical aldehydes and ketones react with HCN.

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14
Q

What does isomerism refer to in chemistry?

A

Isomerism in chemistry refers to the phenomenon where molecules with the same molecular formula have different structural arrangements.

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15
Q

What is the difference between structural isomers and functional group isomers?

A

Structural isomers have the same molecular formula but different structural arrangements, while functional group isomers share the same molecular formula but have atoms arranged to create different functional groups.

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16
Q

What is optical isomerism?

A

Optical isomerism is a type of stereoisomerism that involves the spatial arrangement of atoms.

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17
Q

What are functional group isomers?

A

Functional group isomers have the same molecular formula but different functional groups, such as aldehydes and ketones.

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18
Q

What is biodiesel?

A

Biodiesel is a fuel made from converting vegetable oils with methanol and a strong alkali catalyst. It consists of methyl esters of long-chain carboxylic acids.

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19
Q

What is delocalisation?

A

Delocalisation refers to the spread of electron density over multiple atoms or bonds in a molecule. In the case of carboxylic acids, delocalisation stabilises carboxylic acid salts, enhancing their dissociation.

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20
Q

What is hydrolysis?

A

Hydrolysis is a chemical reaction in which a compound reacts with water, resulting in the breaking of chemical bonds and the formation of new compounds. In the context of esters, hydrolysis can occur with either acid or sodium hydroxide.

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21
Q

What are the products obtained from the hydrolysis of fats and oils?

A

The hydrolysis of fats and oils produces soap, glycerol, and fatty acids.

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22
Q

What is the dual nature of fatty acids used in soaps and how does it help in cleaning?

A

Fatty acids have a hydrophilic end with a polar CO2- group that easily interacts with water and a hydrophobic end with a long non-polar hydrocarbon chain that attracts grease. This dual nature allows the emulsification of grease and water, making it easier to mix and remove them.

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23
Q

How are esters formed and what conditions are required for the reaction?

A

Esters are formed through esterification, a reversible reaction requiring prolonged heating under reflux with an acid catalyst.

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24
Q

How are carboxylic acid salts stabilised?

A

Carboxylic acid salts are stabilised by delocalisation, which enhances dissociation.

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25
Q

How are carboxylic acids named?

A

Carboxylic acids are named with the ending -oic acid and the carbon chain is numbered starting from the carboxylic acid end.

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26
Q

What are some of the uses of esters?

A

Esters have various uses such as solvents, plasticisers, and perfumes.

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27
Q

How can esters undergo hydrolysis and what are the differences between acid and sodium hydroxide hydrolysis?

A

Esters can undergo hydrolysis with either acid or sodium hydroxide, with the latter being a complete and irreversible reaction.

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28
Q

How would you use the properties of glycerol in a practical application?

A

Glycerol can be used in cosmetics, food products, and adhesive formulations due to its ability to readily form hydrogen bonds and its high solubility in water.

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29
Q

What are the properties of carboxylic acids in water?

A

Carboxylic acids are weak acids in water and can displace carbon dioxide from carbonates.

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30
Q

What is the process involved in the oxidation of alcohols using reflux?

A

The oxidation of alcohols using reflux involves a step-by-step process for practical setup and purification of organic liquid from esters produced by reflux.

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31
Q

How can hydrolysis of ethyl benzoate be achieved?

A

Hydrolysis of ethyl benzoate can be achieved by heating under reflux with sodium hydroxide, followed by cooling and addition of hydrochloric acid for filtration of benzoic acid precipitate.

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32
Q

What are acyl chlorides?

A

Acyl chlorides, also known as acid chlorides, are organic compounds that contain the functional group -COCl. They are highly reactive and are commonly used in organic synthesis as acylating agents.

33
Q

What are acid anhydrides?

A

Acid anhydrides are organic compounds that contain two acyl groups (-CO) bonded to an oxygen atom. They are highly reactive and can undergo reactions similar to acyl chlorides.

34
Q

What is a phenol?

A

Phenol is an aromatic compound that contains a hydroxyl group (-OH) attached to a benzene ring. It is a weak acid and can undergo various reactions, including esterification.

35
Q

What is aspirin?

A

Aspirin, also known as acetylsalicylic acid, is a medication commonly used to relieve pain, reduce inflammation, and lower fever. It belongs to the class of drugs known as nonsteroidal anti-inflammatory drugs (NSAIDs).

36
Q

What is the reaction of acyl chlorides with phenol?

A

Acyl chlorides react with phenol to form esters

37
Q

How can acyl chlorides be formed?

A

Acyl chlorides can be formed from carboxylic acids.

38
Q

What are the by-products generated when acyl chlorides and acid anhydrides react?

A

Acyl chlorides release HCl as a by-product, while acid anhydrides produce RCOOH.

39
Q

What transformations of functional groups can acyl chlorides and acid anhydrides undergo?

A

Acyl chlorides and acid anhydrides have similar reactivity and can undergo similar transformations of functional groups.

40
Q

What is transformed into an ester in the process of producing Aspirin?

A

In this process, the phenol group transforms into an ester by reacting with ethanoic anhydride.

41
Q

What is the role of acyl chlorides in acylation reactions with ammonia?

A

Acyl chlorides react with ammonia in acylation reactions.

42
Q

Why are acyl chlorides and acid anhydrides more reactive than carboxylic acids?

A

This increased reactivity is attributed to the presence of chlorine (Cl) and - OCOCH3 groups, which are considered excellent leaving groups.

43
Q

What happens when acyl chlorides react with water?

A

Acyl chlorides react with water to form carboxylic acids.

44
Q

How do acyl chlorides react with alcohols?

A

Acyl chlorides react with alcohols to form esters, which is a faster and non-reversible reaction compared to using carboxylic acids.

45
Q

How is aspirin produced?

A

Aspirin is produced by reacting the phenol group of 2-hydroxybenzoic acid with ethanoic anhydride, which is chosen over acid chlorides for its cost-effectiveness, lower corrosiveness, lower hydrolysis susceptibility, and safer handling.

46
Q

What are aliphatic compounds?

A

Aliphatic compounds are organic substances that can have straight or branched chains. They are characterised by their molecular structure, which consists of carbon atoms bonded together in a linear or branched arrangement.

47
Q

What is thermodynamic stability?

A

Thermodynamic stability refers to the tendency of a compound or a system to remain in a stable state under specific conditions. In the context of benzene, thermodynamic stability is demonstrated by the lower energy requirement for hydrogenation compared to theoretical structures with three double bonds.

48
Q

What is the toxicity of benzene?

A

Benzene is classified as a carcinogen and is highly toxic. It is not allowed to be used in schools due to its harmful effects on health.

49
Q

What is benzene?

A

Benzene is a type of aromatic compound with a molecular formula of C6H6. It has a planar molecular structure and is characterised by its hexagonal ring comprising six carbon atoms, each of which is bonded to a single hydrogen atom.

50
Q

What is a phenyl group?

A

The phenyl group is a substituent side group that can be considered as a derivative of the benzene ring. It is represented by the symbol C6H5- and is commonly used in organic chemistry nomenclature to indicate the presence of a benzene ring as a substituent in a larger molecule.

51
Q

What is delocalised bonding?

A

Delocalised bonding refers to the sharing of electrons over a larger region of a molecule or a compound. In the context of benzene, delocalised bonding refers to the sharing of the six p electrons within the hexagonal ring structure.

52
Q

What are the reactions of benzene?

A

Benzene typically undergoes electrophilic substitution reactions rather than addition reactions due to the delocalised electron system within the ring structure. Electrophilic substitution reactions involve the substitution of one hydrogen atom in benzene with another atom or group of atoms.

53
Q

What are aromatic compounds?

A

Aromatic compounds are organic substances that consist of compounds with one or more rings made up of six carbon atoms and have delocalised bonding. They are characterised by their molecular structure, which consists of a hexagonal ring comprising six carbon atoms, each of which is bonded to a single hydrogen atom.

54
Q

What are enthalpies of hydrogenation and how are they used in aromatic chemistry?

A

Enthalpies of hydrogenation refer to the energy changes that occur when hydrogen gas reacts with a compound. In the context of benzene, enthalpies of hydrogenation are used to compare the energy requirements of different structures and demonstrate the thermodynamic stability of benzene.

55
Q

Describe the molecular structure of benzene and its carbon-carbon bonds.

A

Benzene, an aromatic compound, has a planar molecular structure with equivalent carbon-carbon bonds that exhibit characteristics between single and double bonds.

56
Q

What does the term ‘delocalised’ refer to in the context of benzene’s structure?

A

It refers to the electrons that are not attached to any specific carbon atom and are distributed throughout the entire ring.

57
Q

What type of reactions does benzene typically undergo and why?

A

Benzene typically undergoes electrophilic substitutions because its high electron density makes it attractive to electrophiles and addition reactions would disrupt the delocalised electron system.

58
Q

Under what conditions does benzene react with Br2?

A

Benzene reacts with Br2 only at high temperatures or in the presence of a halogen carrier.

59
Q

How is the thermodynamic stability of the delocalised benzene structure compared to the theoretical structure?

A

The delocalised benzene structure is more thermodynamically stable than the theoretical structure, as shown by the energy level diagram.

60
Q

How do the delocalized pi electrons in benzene contribute to its thermodynamic stability?

A

The delocalized pi electrons in benzene contribute to its thermodynamic stability, as shown by the lower energy requirement in comparison to cyclohexa-1,3,5-triene.

61
Q

What is the structure of benzene and how are the carbon atoms bonded?

A

The structure of benzene consists of a hexagonal ring with each carbon atom bonded to a hydrogen atom and possessing an unused electron in a p orbital.

62
Q

What is the relationship between the bond lengths in benzene and the bond lengths in a C=C double bond and a C-C single bond?

A

The bond lengths in benzene are intermediate between those of a C=C double bond and a C-C single bond.

63
Q

What is the difference between aliphatic and aromatic compounds?

A

Aliphatic compounds are organic substances with straight or branched chains, while aromatic compounds consist of rings made up of six carbon atoms and have delocalised bonding.

64
Q

What is the difference in stability between cyclohexa-1,4-diene and cyclohexa-1,3-diene?

A

The lack of delocalisation in cyclohexa-1,4-diene results in less stability compared to cyclohexa-1,3-diene, where some delocalisation occurs.

65
Q

What is the process for naming aromatic molecules with multiple substituents?

A

Naming aromatic molecules involves indicating the positions of substituents using numerical prefixes and following alphabetical order for multiple substituents.

66
Q

What is halogenation?

A

Halogenation is an electrophilic substitution reaction in which a halogen atom (such as bromine or chlorine) is introduced onto the benzene ring. This reaction requires a halogen carrier chemical, such as iron(III) bromide or aluminum chloride, to facilitate the reaction.

67
Q

What are substituents?

A

Substituents are atoms or groups of atoms that replace hydrogen atoms in a molecule. In the context of benzene, substituents refer to the atoms or groups of atoms attached to the benzene ring.

68
Q

What is nitration?

A

Nitration is a specific electrophilic substitution reaction of benzene in which a nitro group (-NO2) is introduced onto the benzene ring. This reaction involves the use of concentrated nitric acid with concentrated sulfuric acid as a catalyst.

69
Q

What is acylation?

A

Friedel-Crafts acylation is an electrophilic substitution reaction in which an acyl group is introduced onto the benzene ring. This reaction involves the use of an acyl chloride and anhydrous aluminum chloride as a catalyst.

70
Q

What is Friedel Crafts acylation?

A

Friedel Crafts acylation is an electrophilic substitution reaction that allows the addition of acyl groups to the benzene ring.

71
Q

Why is benzene prohibited for use in schools?

A

Benzene is toxic and a carcinogen, making it prohibited for use in schools. Methylbenzene, which is less toxic, reacts more readily than benzene due to the electron-releasing effect of the methyl group.

72
Q

What is the phenyl group?

A

The phenyl group is a substituent group derived from benzene that can be considered as a substituent group resembling alkyl groups.

73
Q

Why does benzene require additional halogen carrier chemicals to react with bromine compared to alkenes?

A

Unlike alkenes, benzene requires additional halogen carrier chemicals to react with bromine because its delocalised π-bond electrons result in lower electron density and a weaker dipole in bromine.

74
Q

What is the first step in the formation of an electrophile in electrophilic substitution reactions?

A

The first step in the formation of an electrophile in electrophilic substitution reactions involves the abstraction of a proton from sulfuric acid by HNO3.

75
Q

How are benzene derivatives named?

A

Benzene derivatives are named by indicating the positions of multiple substituents on the benzene ring using the lowest possible numbers and listing them alphabetically

76
Q

At what temperature does the reaction with benzene occur in electrophilic substitution reactions?

A

The reaction with benzene in electrophilic substitution reactions occurs at 60°C, and at higher temperatures, a second nitro group can be added.

77
Q

Why does methylbenzene react more readily than benzene?

A

The methyl group releases electrons into the delocalised system, making it more attractive to electrophiles.

78
Q

What is the significance of the nitration of benzene?

A

It plays a role in synthesising valuable compounds, such as explosives like TNT, and in the production of amines used for making dyestuffs.

79
Q

How is the electrophile, +NO2, formed in electrophilic substitution reactions?

A

The electrophile, +NO2, is formed in electrophilic substitution reactions through the elimination of a water molecule from the intermediate.