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organic chemistry 3 Flashcards

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1
Q

what is the formula for benzene

A

C₆H₆

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2
Q

what are the two ways of representing benzene

A

kekule model delocalised model

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3
Q

What was Friedrich August Kekulé’s proposal about the structure of benzene?

A

Kekulé proposed that benzene was made up of a planar (flat) ring of carbon atoms with alternating single and double bonds between them.

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4
Q

What additional atoms did Kekulé propose were bonded to each carbon atom in benzene?

A

In Kekulé’s model, each carbon atom is also bonded to one hydrogen atom.

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5
Q

How did Kekulé adapt his model of the benzene molecule?

A

He later adapted the model to propose that the benzene molecule was constantly flipping between two forms (isomers) by switching over the double and single bonds.

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6
Q

What would you expect the bond lengths to be in benzene according to the Kekulé model?

A

According to the Kekulé model, you’d expect benzene to have three bonds with the length of a C–C bond (154 pm) and three bonds with the length of a C=C bond (134 pm).

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7
Q

What have X-ray diffraction studies revealed about the carbon-carbon bonds in benzene?

A

X-ray diffraction studies have shown that all the carbon-carbon bonds in benzene have the same length of 140 pm, which is between the length of a single bond and a double bond.

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8
Q

What does the consistency in bond lengths observed in benzene indicate about the Kekulé model?

A

The consistent bond length of 140 pm observed in benzene suggests that the Kekulé structure cannot be entirely accurate.

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9
Q

What does the delocalised model propose about the bonding in benzene?

A

The delocalised model proposes that benzene’s bonding involves delocalised pi-bonds formed by the overlapping of p-orbitals on carbon atoms.

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10
Q

How are sigma-bonds formed in the delocalised model of benzene?

A

In the delocalised model, each carbon atom forms three s-bonds—one to a hydrogen atom and one to each of its neighboring carbon atoms—due to head-on overlap of their atomic orbitals.

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11
Q

What happens to the remaining p-orbital on each carbon atom in the delocalised model of benzene?

A

Each carbon atom has one remaining p-orbital containing one electron, which overlaps sideways with the p-orbitals of neighboring carbon atoms to form a ring of delocalised p-bonds.

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12
Q

How are the electrons in the delocalised model of benzene represented, and why?

A

The electrons in the delocalised model are represented as a circle inside the ring of carbons rather than as double or single bonds because they are delocalised and do not belong to a specific carbon atom.

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13
Q

What happens when you react an alkene with hydrogen gas?

A

Two atoms of hydrogen add across the double bond, a process known as hydrogenation, and the enthalpy change of the reaction is called the enthalpy change of hydrogenation.

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14
Q

What is the expected enthalpy change of hydrogenation for benzene based on the Kekulé structure?

A

If benzene had three double bonds (as in the Kekulé structure), the expected enthalpy change of hydrogenation would be (3 × 120 =) –360 kJ mol–1.

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15
Q

when cyclohexane is hydrogenated what is the enthalpy change of hydrogenation

A

-120 kj mol⁻¹

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16
Q

What is the experimental enthalpy change of hydrogenation for benzene, and how does it compare to the expected value?

A

The experimental enthalpy change of hydrogenation for benzene is –208 kJ mol–1, which is far less exothermic than the expected value.

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17
Q

What conclusion can be drawn from the discrepancy between the expected and experimental enthalpy changes of hydrogenation for benzene?

A

The discrepancy suggests that more energy must have been put in to break the bonds in benzene than would be needed to break the bonds in the Kekulé structure.

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18
Q

What does the discrepancy between the expected and experimental enthalpy changes of hydrogenation for benzene indicate about its stability?

A

The difference indicates that benzene is more stable than the Kekulé structure would be.

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19
Q

what does the difference in in energy indicate about benzene and the kekule model

A

This difference indicates that benzene is more stable than the Kekulé structure would be.

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20
Q

What is thought to be the reason for benzene’s extra stability compared to the Kekulé structure?

A

The extra stability of benzene is thought to be due to the delocalised ring of electrons.

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21
Q

How do alkenes react with bromine water at room temperature, and what is the result?

A

Alkenes react easily with bromine water at room temperature, decolorizing the brown bromine water. This reaction is an electrophilic addition reaction, where the bromine atoms are added across the double bond of the alkene.

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22
Q

What is the expected reaction between benzene and bromine based on the Kekulé structure, and what are the actual conditions required for this reaction?

A

Based on the Kekulé structure, one would expect a similar reaction between benzene and bromine. However, to make it happen, you need hot benzene and ultraviolet light, and it remains difficult.

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23
Q

How is the difference in reactivity between benzene and other alkenes explained?

A

The difference is explained by the presence of delocalized p-bonds in benzene, which spread out the negative charge and make the benzene ring very stable. Therefore, benzene is reluctant to undergo addition reactions that would destroy the stable ring.

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24
Q

what type of reaction does benzene prefer to undergo, and why?

A

Benzene prefers to undergo electrophilic substitution reactions instead of addition reactions. This is because in alkenes, the p-bond in the C=C double bond attracts electrophiles strongly due to its localized high electron density. In benzene, however, this attraction is reduced due to the negative charge being spread out.

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25
What happens when benzene is burned in oxygen?
When benzene is burned in oxygen, it produces carbon dioxide and water.
26
What occurs if benzene is burned in air?
2C₆H₆ + 15O₂ ⟶ 12CO₂ + 6H₂O If benzene is burned in air, a very smoky flame is produced due to insufficient oxygen for complete combustion. Many carbon atoms remain unburned and form particles of soot in the hot gas, resulting in a smoky flame.
27
what happens when you burn benzene in air
If you burn benzene in air, you get a very smoky flame — there’s too little oxygen to burn the benzene completely. A lot of the carbon atoms stay as carbon and form particles of soot in the hot gas — making the flame smoke.
28
What are compounds containing a benzene ring commonly called?
arenes or ‘aromatic compounds’
29
Why doesn't benzene undergo electrophilic addition reactions like alkenes?
Benzene doesn't undergo electrophilic addition reactions like alkenes because addition reactions would break the very stable ring of delocalised pi-bonds.
30
Describe the process of electrophilic substitution reactions in benzene.
In electrophilic substitution reactions, a hydrogen atom in benzene is substituted by an electrophile.
31
What are the two steps involved in the mechanism of electrophilic substitution reactions in benzene?
The mechanism involves two steps: addition of the electrophile to form a positively charged intermediate, followed by loss of H+ from the carbon atom attached to the electrophile, reforming the delocalised ring.
32
Why does an electrophile need to have a strong positive charge to attack the benzene ring?
The delocalised p-bonds in benzene spread out the charge density across the ring, requiring an electrophile with a strong positive charge to effectively attack the benzene ring.
33
How can some compounds be made into stronger electrophiles for attacking the benzene ring?
Some compounds can be made into stronger electrophiles using a catalyst called a halogen carrier.
34
What role does a halogen carrier play in making compounds stronger electrophiles?
a halogen carrier polarises halogens such as br2 and cl2 the positive part of the halogen acts as the electrophile
35
Name some examples of halogen carriers.
Halogen carriers include aluminium halides, iron halides, and iron.
36
What are Friedel-Crafts reactions used for in organic synthesis?
Friedel-Crafts reactions are used for forming C–C bonds in organic synthesis.
37
What are the two types of Friedel-Crafts reactions?
The two types are Friedel-Crafts alkylation and Friedel-Crafts acylation.
38
Describe Friedel-Crafts alkylation.
Friedel-Crafts alkylation puts any alkyl group onto a benzene ring using a halogenoalkane and a halogen carrier.
39
Describe Friedel-Crafts acylation.
Friedel-Crafts acylation substitutes an acyl group for a hydrogen atom on benzene, typically using an acyl chloride instead of a halogenoalkane.
40
What conditions are required for Friedel-Crafts reactions to occur?
The reactants need to be heated under reflux in a non-aqueous solvent (like dry ether) for Friedel-Crafts reactions to occur.
41
What happens when benzene is warmed with concentrated nitric acid and concentrated sulfuric acid?
When benzene is warmed with concentrated nitric acid and concentrated sulfuric acid, a nitration reaction occurs, and nitrobenzene is formed.
42
What role does sulfuric acid play in the nitration reaction of benzene?
Sulfuric acid acts as a catalyst in the nitration reaction of benzene, facilitating the formation of the nitronium ion (NO2+), which is the electrophile.
43
what is the formula for phenol
C₆H₅OH
44
What property of phenol makes it more likely to undergo electrophilic substitution than benzene?
The presence of the -OH group makes phenol more likely to undergo electrophilic substitution than benzene.
45
How does the lone pair of electrons from the oxygen atom in the -OH group of phenol contribute to its reactivity?
One of the lone pairs of electrons in a p-orbital of the oxygen atom overlaps with the delocalised p-bonds in the benzene ring, causing the lone pair of electrons from the oxygen atom to be partially delocalised into the p-system.
46
How does the partial delocalization of the lone pair of electrons from the oxygen atom affect the reactivity of phenol?
This increases the electron density of the ring, making it more likely to be attacked by electrophiles.
47
How does phenol react with orange bromine water?
Phenol reacts with orange bromine water, causing it to decolorize.
48
Why does substitution occur more than once when phenol reacts with electrophiles?
The -OH group in phenol makes the ring highly attractive to electrophiles, leading to multiple substitution reactions.
49
What is the product formed when phenol reacts with orange bromine water, and what are its properties?
The product formed is 2,4,6-tribromophenol, which is insoluble in water and precipitates out of the mixture. It has a characteristic antiseptic smell.
50
How can aspirin be synthesized using phenol?
Aspirin can be synthesized through an esterification reaction of salicylic acid, which is a derivative of phenol.
51
What steps are involved in the synthesis of aspirin from salicylic acid?
1. Add ethanoic anhydride and a few drops of phosphoric acid to salicylic acid in a test tube. 2. Warm the reaction mixture to 50 °C and leave it for about 15 minutes. 3. Add cold water to the reaction mixture, then cool it on ice to allow aspirin crystals to form. 4. Filter the crystals under reduced pressure. 5. Recrystallize the aspirin in a mixture of water and ethanol.
52
What is an amine?
An amine is a compound derived from ammonia (NH3) where one or more of the hydrogens is replaced with an organic group.
53
what is the functional group of a amine
The functional group of amines is -NR2, where R is an alkyl group or hydrogen.
54
How are amines classified based on the number of alkyl groups bonded to the nitrogen atom?
Amines can be classified as primary, secondary, or tertiary depending on how many alkyl groups the nitrogen atom is bonded to.
55
What is a quaternary ammonium ion?
A quaternary ammonium ion is formed when the nitrogen atom in ammonia is bonded to four alkyl groups, resulting in a positively charged ion.
56
How can amines be synthesized using halogenoalkanes and ethanolic ammonia?
Amines can be synthesized by heating a halogenoalkane with an excess of ethanolic ammonia.
57
What is the limitation of synthesizing amines using halogenoalkanes and ethanolic ammonia?
The limitation is that this method yields a mixture of primary, secondary, and tertiary amines, as well as quaternary ammonium salts.
58
Why does the reaction of halogenoalkanes with ethanolic ammonia result in a mixture of different types of amines?
The nitrogen atom in primary, secondary, and tertiary amines has a lone pair of electrons, allowing it to act as a nucleophile. It can participate in nucleophilic substitution reactions with any halogenoalkane in the reaction mixture, leading to the production of more substituted amines where more than one hydrogen is replaced.
59
How can a nitrile be reduced to a primary amine in the laboratory?
A nitrile can be reduced to a primary amine in the laboratory using lithium aluminium hydride (LiAlH4) in a non-aqueous solvent, followed by treatment with dilute acid.
60
What is the industrial method for reducing nitriles to primary amines?
In industry, nitriles are reduced to primary amines using hydrogen gas with a metal catalyst, such as platinum or nickel, at high temperature and pressure. This process is called catalytic hydrogenation.
61
How are aromatic nitro compounds reduced to aromatic amines in two steps?
1) Heat a mixture of a nitro compound, tin metal, and concentrated hydrochloric acid under reflux to form a salt. 2) To obtain the aromatic amine, add sodium hydroxide.
62
Why do amines act as weak bases?
Amines act as weak bases because they accept protons. The lone pair of electrons on the nitrogen atom can form a dative covalent (coordinate) bond with an H+ ion.
63
What factors influence the strength of a base in amines?
The strength of the base depends on the availability of the lone pair of electrons on the nitrogen atom. The more available the lone pair is, the more likely the amine is to accept a proton, and the stronger a base it will be.
64
How does the availability of the lone pair of electrons affect the strength of a base in amines?
A lone pair of electrons will be more available if its electron density is higher, making the amine more likely to accept a proton and stronger as a base.
65
How does the basicity of primary aliphatic amines compare to that of ammonia and aromatic amines?
Primary aliphatic amines are stronger bases than ammonia, which is stronger than aromatic amines.
66
Why are primary aliphatic amines stronger bases than ammonia?
Alkyl groups attached to primary aliphatic amines push electrons onto the nitrogen atom, increasing the electron density on the nitrogen and making the lone pair more available, resulting in stronger basicity.
67
Why are aromatic amines weaker bases compared to primary aliphatic amines?
The benzene ring in aromatic amines draws electrons towards itself, causing partial delocalization of the nitrogen lone pair onto the ring. This decreases the electron density on the nitrogen, making the lone pair less available and resulting in weaker basicity.
68
What type of reactions do amines undergo with halogenoalkanes and acyl chlorides?
Amines undergo nucleophilic substitution reactions with halogenoalkanes and react with acyl chlorides to form N-substituted amides.
69
How do amines react with acids?
Amines react with acids to form ammonium salts.
70
What is the reaction between butylamine and hydrochloric acid?
Butylamine reacts with hydrochloric acid to form butylammonium chloride.
71
why are small amines soluble in water
Small amines are soluble in water because the amine group can form hydrogen bonds with water molecules.
72
Why are larger amines less soluble in water than small ones?
Larger amines have greater London forces between molecules, requiring more energy to overcome. Additionally, the larger carbon chains disrupt hydrogen bonding with water. Thus, large amines are less soluble in water.
73
when amines dissolve they from alkaline solutions so what happens to some of the amine molecules
When they dissolve, amines form alkaline solutions. Some of the amine molecules in the solution take a hydrogen ion from water, forming alkyl ammonium ions and hydroxide ions.
74
in copper (II) sulfate solution what do the Cu²⁺ ions do with water
from the [Cu(H₂O)₆]²⁺ complex
75
what colour is the solution of the complex [Cu(H₂O)₆]²⁺
blue
76
what happens if you add butylamine solution to copper (II) sulfate
you get a pale blue precipitate — the amine acts as a base (proton acceptor) and takes two H+ ions from the complex. This leaves a pale blue precipitate of copper hydroxide, [Cu(OH)₂(H₂O)₄], which is insoluble.
77
what happens If you add excess butylamine to the coppersulfate solution
dd more butylamine solution, and the precipitate dissolves to form a beautiful deep blue solution. Some of the ligands are replaced by butylamine molecules, which donate their lone pairs to form dative covalent bonds with the Cu2+ ion. This forms soluble [Cu(CH₃(CH₂)₃NH₂)₄(H₂O)₂]²⁺ complex ions.
78
What is the reaction mechanism for forming primary amines from ammonia and halogenoalkanes?
Nucleophilic substitution reaction — the lone pair on the ammonia molecule reacts with the d+ carbon in the halogenoalkane, displacing the halogen and forming a primary amine.
79
What property of primary amines makes them nucleophiles?
The nitrogen atom in primary amines has a lone pair of electrons, making it a nucleophile.
80
Do primary, secondary, and tertiary amines all possess a lone pair of electrons on their nitrogen atom?
Yes, primary, secondary, and tertiary amines all have a lone pair of electrons on their nitrogen atom.
81
How do primary, secondary, and tertiary amines react with halogenoalkanes?
They undergo nucleophilic substitution reactions, where they replace the halogen atom in the halogenoalkane to form more substituted amines.
82
What happens when amines react with acyl chlorides?
An H atom on the amine is replaced by the acyl group, RCO, to form an N-substituted amide and HCl. The produced HCl further reacts with another molecule of the amine to generate a salt.
83
what functional group do amides have
-CONH₂
84
How does the carbonyl group affect the behavior of amides compared to amines?
The carbonyl group in amides withdraws electrons, causing amides to behave differently from amines.
85
What are the two types of amides that can be formed, and what determines their structure?
Primary amides and N-substituted amides. Their structure depends on the number of carbon atoms the nitrogen is bonded to.
86
What is the naming convention for primary amides?
Primary amides are named by using the stem of the carbon chain followed by the suffix -amide.
87
How are N-substituted amides named?
N-substituted amides are named using the prefix N-alkyl- to describe the alkyl chain attached directly to the nitrogen atom.
88
What happens when an acyl chloride reacts with ammonia or a primary amine?
An amide is formed.
89
What type of amide is formed when an acyl chloride reacts with concentrated ammonia at room temperature?
A primary amide is formed.
90
What type of amide is formed when an acyl chloride reacts with a primary amine at room temperature?
An N-substituted amide is formed.
91
What is typically involved in condensation polymerization?
Condensation polymerization typically involves two different types of monomers.
92
What is the role of functional groups in condensation polymerization?
Each monomer has at least two functional groups, and each functional group reacts with a group on another monomer to form a link, creating polymer chains.
93
Why is it called condensation polymerization?
Condensation polymerization is named because each time a link is formed, a small molecule (often water) is lost.
94
What reaction occurs between carboxyl (–COOH) groups and amino (–NH2) groups?
They react to form amide (–CONH–) links.
95
What happens each time an amide link is formed between carboxyl and amino groups?
A water molecule is lost, indicating a condensation reaction.
96
What type of polymer is formed through the condensation reaction between carboxyl and amino groups?
A polyamide is formed.
97
What functional groups are present in amino acids?
Amino acids contain both an amine and a carboxylic acid group.
98
How do amino acid monomers form proteins through polymerization?
Amino acid monomers undergo condensation polymerization reactions, forming proteins linked by amide links, also known as peptide links.
99
What type of reaction occurs between the amine group of one amino acid and the carboxylic acid group of another?
In a condensation reaction, the amine group of one amino acid reacts with the carboxylic acid group of another to form an amide link.
100
How can you break down a protein into its individual amino acids?
You can hydrolyze a protein using hot aqueous 6 mol dm–3 hydrochloric acid under reflux for 24 hours. This produces the ammonium salts of the amino acids, which are then neutralized using a base.
101
What method can be used to identify the amino acid monomers of a hydrolyzed protein?
Chromatography can be used to identify the amino acid monomers that a protein was made from.
102
What reaction occurs between carboxyl groups (–COOH) and hydroxyl groups (–OH)?
They react to form ester links (–COO–).
103
What type of reaction is the formation of ester links between carboxyl and hydroxyl groups?
It's another condensation reaction.
104
What type of polymer is formed through the condensation reaction between carboxyl and hydroxyl groups?
A polyester is formed.
105
How can you determine the formulae of monomers used to make a condensation polymer?
1. Find the amide (HN–CO) or ester (CO–O) link in the repeat unit. 2. Break it down the middle. 3. Add an H or an OH to both ends of both molecules to find the monomers. 4. Always add Hs to O or N atoms and OH groups to C atoms.
106
How can you determine the repeat unit of a condensation polymer formed from a pair of monomers?
1. Draw out the two monomer molecules next to each other. 2. Remove an OH from the dicarboxylic acid and an H from the diamine to form a water molecule. 3. Join the carbon and the nitrogen together to make an amide link. 4. Remove another H and OH from the ends of the molecule to find the repeat unit.
107
What are amino acids often referred to as?
Amino acids are often called the building blocks of life.
108
What are amino acids primarily used for in the body?
Amino acids are primarily used to make all the proteins in the body.
109
What functional groups does an amino acid contain?
An amino acid contains a basic amino group (NH2) and an acidic carboxyl group (COOH).
110
Why are amino acids considered amphoteric?
Amino acids are considered amphoteric because they possess both acidic and basic properties.
111
What distinguishes 2-amino acids from other types of amino acids?
2-amino acids are the type of amino acids found in nature, with the amino group positioned on carbon-2 (the carboxyl group is always carbon-1).
112
What is a zwitterion?
A zwitterion is an overall neutral molecule that has both a positive and a negative charge in different parts of the molecule.
113
Under what conditions can an amino acid exist as a zwitterion?
An amino acid can only exist as a zwitterion near its isoelectric point, which is the pH where the overall charge on the amino acid is zero.
114
What factors determine the isoelectric point of an amino acid?
The isoelectric point of an amino acid depends on its R group, and it varies for different amino acids.
115
What happens to the –NH2 group of an amino acid in conditions more acidic than its isoelectric point?
The –NH2 group is likely to be protonated.
116
What is the state of the carboxyl and amino groups of an amino acid at its isoelectric point?
At the isoelectric point, both the carboxyl group and the amino group are likely to be ionized, forming a zwitterion.
117
What happens to the –COOH group of an amino acid in conditions more basic than its isoelectric point?
The –COOH group is likely to lose its proton.
118
Under what condition will an amino acid exist as a zwitterion when dissolved in solution?
If the amino acid contains the same number of carboxyl groups as amino groups, it will exist as a zwitterion.
119
What is the pH of a zwitterionic amino acid solution?
A zwitterionic amino acid solution will have a pH of about 7, making it roughly neutral.
120
What are the four different groups attached to carbon-2 of a 2-amino acid?
The carboxyl group, the amino group, a hydrogen atom, and the R group.
121
Why are 2-amino acids considered chiral molecules?
2-amino acids are considered chiral molecules because they have four different groups attached to carbon-2, resulting in two optical isomers.
122
What happens when plane-polarized, monochromatic light passes through an aqueous solution containing one enantiomer of a 2-amino acid?
The plane of the light gets rotated due to the presence of the chiral carbon.
123
What is the exception to the rule of enantiomers rotating the plane of plane-polarized light?
Glycine is the exception. It has two H atoms attached to the central carbon, making it achiral, and it won't rotate the plane of plane-polarized light.
124
What is the general formula for Grignard reagents?
The general formula for Grignard reagents is RMgX, where R is an alkyl group and X is a halogen.
125
How are Grignard reagents typically prepared?
Grignard reagents are prepared by refluxing a halogenoalkane with magnesium in dry ether.
126
Provide an example of the preparation of a Grignard reagent.
Refluxing bromoethane with magnesium in dry ether would create the following Grignard reagent.
127
What are the two steps to make a carboxylic acid from a Grignard reagent
1) Bubble carbon dioxide gas through a Grignard reagent in dry ether. 2) Add a dilute acid, such as hydrochloric acid.
128
What happens during the reaction between carbon dioxide and a Grignard reagent?
During the reaction, a new C–C bond forms between the carbon atom in carbon dioxide and the C–Mg carbon from the Grignard reagent. One of the C=O bonds in carbon dioxide is broken to form a -COO– group, which is protonated when the dilute acid is added to form a carboxylic acid (-COOH).
129
What happens when Grignard reagents react with aldehydes and ketones?
Grignard reagents react with aldehydes and ketones to make alcohols. A new C–C bond forms between the C–Mg carbon atom from the Grignard reagent and the C=O carbon of the carbonyl. This causes the C=O bond to break, and when acid is added, an -OH group is formed.
130
What type of reactions does benzene participate in instead of electrophilic addition reactions?
Benzene participates in electrophilic substitution reactions instead of electrophilic addition reactions.

chem (16 decks)

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