Benzene Chemistry Quiz

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Questions and Answers

What type of hybridization do all the carbon atoms in benzene undergo?

  • sp2 hybridization (correct)
  • d2sp3 hybridization
  • sp3 hybridization
  • sp hybridization

How many sigma (σ) bonds does each carbon atom in benzene form?

  • Four
  • One
  • Two
  • Three (correct)

What is the nature of the electrons involved in the π bonding system of benzene?

  • They are localized between two carbon atoms.
  • They are delocalized over all six carbon atoms. (correct)
  • They are fixed in position above and below the plane.
  • They are tightly bound to individual carbon atoms.

What is the bond angle around each sp2 hybridized carbon atom in benzene?

<p>120° (A)</p> Signup and view all the answers

Which of the following statements about π bonds in benzene is true?

<p>They result from the overlap of p atomic orbitals. (A)</p> Signup and view all the answers

What is the structural representation of phenylamine?

<p>C6H5NH2 (C)</p> Signup and view all the answers

How are the positions of substituent groups indicated when naming aryl compounds?

<p>By numbering the carbon atoms in the benzene ring (D)</p> Signup and view all the answers

Which of the following compounds is a substituted benzene?

<p>Nitrobenzene (B)</p> Signup and view all the answers

What is the product formed during the sulfonation of benzene?

<p>Benzenesulfonic acid (A)</p> Signup and view all the answers

Which molecule acts as the electrophile in the sulfonation of benzene?

<p>SO3 (A)</p> Signup and view all the answers

What is the role of aluminium chloride in Friedel–Crafts reactions?

<p>It acts as a catalyst. (D)</p> Signup and view all the answers

What type of group is introduced into the benzene ring during Friedel-Crafts alkylation?

<p>Alkyl group (B)</p> Signup and view all the answers

What functional group characterizes an acyl group in Friedel-Crafts reactions?

<p>Carbonyl group (D)</p> Signup and view all the answers

In the mechanism of Friedel-Crafts reactions, what is the first step to generate the electrophile?

<p>Formation of a dative bond between alkyl halide and aluminium chloride (D)</p> Signup and view all the answers

What type of reaction is sulfonation considered to be?

<p>Electrophilic substitution (B)</p> Signup and view all the answers

Which atom in the SO3 molecule is primarily involved in accepting an electron pair during sulfonation?

<p>Sulfur atom (C)</p> Signup and view all the answers

What type of groups activate the positions of the benzene ring?

<p>Electron-donating groups (B)</p> Signup and view all the answers

When excess chlorine gas is used with methylbenzene, which of the following products is NOT formed?

<p>Bromomethylbenzene (C)</p> Signup and view all the answers

What is the characteristic of the carbon–halogen bond in halogenoarenes?

<p>It has partial double bond character (C)</p> Signup and view all the answers

What type of reaction occurs when chlorine reacts with alkanes in the presence of UV light?

<p>Free-radical substitution (C)</p> Signup and view all the answers

If bromine is added to methylbenzene in the presence of aluminium bromide, what main product is expected?

<p>Tribromomethylbenzene (C)</p> Signup and view all the answers

How does the reaction of methylbenzene and bromine differ when boiled in the presence of UV light?

<p>All hydrogen atoms on the methyl side-chain are replaced (B)</p> Signup and view all the answers

What mechanism is involved in electrophilic substitution reactions of benzene?

<p>Electrophilic substitution mechanism (A)</p> Signup and view all the answers

Which positions in substituted arenes are considered equivalent during substitution reactions?

<p>2 and 6 positions (B)</p> Signup and view all the answers

What happens to the delocalised electrons in benzene during electrophilic substitution?

<p>They remain intact and stabilize the ring. (C)</p> Signup and view all the answers

How is the electrophile created in the electrophilic substitution of benzene with bromine?

<p>Through the action of aluminum bromide polarizing bromine. (A)</p> Signup and view all the answers

Which catalysts are known as halogen carriers in benzene reactions?

<p>Aluminum chloride and aluminum bromide. (D)</p> Signup and view all the answers

What effect does an addition reaction have on the benzene ring's aromatic stabilization?

<p>It disrupts the aromatic stabilization. (A)</p> Signup and view all the answers

In the electrophilic substitution mechanism, what do the curly arrows represent?

<p>Movement of a pair of electrons. (B)</p> Signup and view all the answers

When methylbenzene undergoes electrophilic substitution, where does the halogen atom typically substitute?

<p>At the 2 or 4 position. (A)</p> Signup and view all the answers

What type of bonding is present in benzene?

<p>Delocalized π bonding. (A)</p> Signup and view all the answers

What is the primary characteristic of the benzene ring that allows it to react with electrophiles?

<p>Its high electron density. (B)</p> Signup and view all the answers

What is the first step in the acylation of benzene?

<p>The electrophile attacks the benzene ring. (D)</p> Signup and view all the answers

What happens to the alkane side-chain of alkylarenes during oxidation?

<p>It gets oxidized to form a carboxylic acid. (A)</p> Signup and view all the answers

Which catalyst is used in the hydrogenation of benzene?

<p>Nickel or platinum (A)</p> Signup and view all the answers

What is the product formed when methylbenzene is hydrogenated?

<p>Methylcyclohexane (A)</p> Signup and view all the answers

What is the electrophile involved in the nitration process?

<p>NO2+ ion (A)</p> Signup and view all the answers

What is the main purpose of the nitrating mixture of concentrated nitric acid and sulfuric acid?

<p>To generate the nitronium ion (A)</p> Signup and view all the answers

What is the final step in the mechanism for alkylation of benzene?

<p>Regeneration of the aluminium chloride catalyst. (A)</p> Signup and view all the answers

In the first stage of nitration, what happens to the electron pair from the benzene ring?

<p>It is donated to the nitronium ion (A)</p> Signup and view all the answers

What type of product is formed when benzene reacts with chloroalkanes in alkylation?

<p>Benzene derivatives (A)</p> Signup and view all the answers

What is produced from the oxidation of hexylbenzene using alkaline potassium manganate(VII)?

<p>Benzoic acid (D)</p> Signup and view all the answers

What happens to the benzene ring’s electron system during nitration?

<p>Its delocalized system is temporarily disrupted (B)</p> Signup and view all the answers

Which reaction classifies the conversion of benzene to cyclohexane?

<p>Addition (A)</p> Signup and view all the answers

Which positions on the benzene ring are preferred during further nitration of nitrobenzene?

<p>3 and 5 positions (B)</p> Signup and view all the answers

What type of effect does the nitro group exhibit in the context of nitration reactions?

<p>Electron-withdrawing effect (A)</p> Signup and view all the answers

What is formed as a by-product when nitration occurs?

<p>Hydrogen ion (H+) (A)</p> Signup and view all the answers

What is the name of one of the products formed from the nitration of methylbenzene?

<p>2,4-dinitromethylbenzene (B)</p> Signup and view all the answers

Flashcards

Delocalization in benzene

The process in which the electrons in the π bonding system of benzene are not localized to specific carbon atoms but are spread out over all six carbon atoms.

π bonding in benzene

Each carbon atom in benzene contributes one electron to form a π bond, which is not a localized bond between two carbon atoms like in alkenes, but is spread over all six carbon atoms.

σ bonding in benzene

The three σ bonds that each carbon atom forms in benzene: one with each neighboring carbon atom and one with a hydrogen atom.

Aryl compounds

Aromatic compounds with a functional group directly attached to the benzene ring.

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Electrons in the π bonding of Benzene

The number of electrons involved in the π bonding system of a benzene molecule.

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Skeletal formula of Benzene

A shorthand way to write the benzene ring structure, using a circle to represent the delocalized π electron system.

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Phenyl group

The group of carbon atoms and their attached hydrogen atoms that are derived from a benzene ring when one hydrogen atom is removed.

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Phenylamine

A compound with a nitrogen atom directly attached to the benzene ring.

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Electrophilic Substitution

A type of chemical reaction where an atom or group of atoms is exchanged for another atom or group of atoms, while the overall structure of the molecule remains largely unchanged. In benzene, this involves replacing one or more hydrogen atoms with another atom or group.

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Electrophile

A compound that is attracted to areas of high electron density. In the context of arenes, they are often positively charged species that attack the electron-rich benzene ring.

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Br+ Cation

A positively charged species (cation) that is formed when a Br2 molecule reacts with AlBr3 in the presence of benzene. This species is an electrophile and initiates the electrophilic substitution reaction by attacking the benzene ring.

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Delocalized Electrons in Benzene

The electrons in the π bonding system of benzene are not localized to specific carbon atoms but are spread out over all six carbon atoms. This creates a highly stable ring and explains the resistance of benzene to addition reactions.

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1,3,5-Tribromobenzene

A molecule containing a benzene ring with three bromine atoms attached at positions 1, 3, and 5 on the ring.

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1,3-Dichloro-5-nitrobenzene

A molecule containing a benzene ring with two chlorine atoms attached at positions 1 and 3, and a nitro group attached at position 5.

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Arenes

A group of molecules that have a benzene ring as their core structure. These molecules often undergo electrophilic substitution reactions due to the electron-rich nature of the benzene ring.

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Nitration

Involves the introduction of a nitro group (-NO2) into a molecule using an electrophilic substitution reaction.

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Nitronium Ion

The positively charged NO2+ ion, formed from nitric acid and sulfuric acid, acting as the attacking species in nitration.

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Nitrating Mixture

The mixture of concentrated nitric acid and concentrated sulfuric acid used to generate the nitronium ion for nitration.

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Electrophilic Aromatic Substitution

A reaction where an electrophile (electron-seeking species) attacks a benzene ring, replacing a hydrogen atom with the electrophile.

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Deactivating Effect of Nitro group

The nitro group (-NO2) attached to a benzene ring makes the ring less reactive towards further electrophilic aromatic substitution at the 2 and 4 positions.

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Directing Effect of Substituents

The tendency of a substituent on a benzene ring to direct further electrophilic substitution to specific positions.

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Nitrobenzene

The product formed by the nitration of methylbenzene (toluene), where a nitro group is added to the benzene ring.

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Mono-Substituted Nitro Toluene

The product formed by the nitration of toluene where the nitro group is located at the 2, 4, or 6 positions relative to the methyl group.

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Electrophilic Aromatic Halogenation

The substitution of a hydrogen atom on a benzene ring with a halogen atom, using a Lewis acid catalyst like aluminum chloride.

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Free Radical Halogenation of Alkyl Side Chains

A reaction where a hydrogen atom on an alkyl side chain of an aromatic compound is replaced by a halogen atom. This is a free radical reaction.

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Electron-donating group

The ability of an atom or group to donate electrons, making the molecule more reactive.

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Multi-Substitution in Benzene

When multiple substitutions occur on the benzene ring, especially if they occur at the 2, 4, and 6 positions, because these positions are activated by the electron-donating groups.

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Reactivity of Aromatic Compounds

The C-H bond in the benzene ring is less reactive than the C-H bond in an alkane due to the electron delocalization in the benzene ring.

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Nitration of Benzene

The nitration of benzene involves the introduction of a nitro group (-NO2) onto the benzene ring, using concentrated nitric acid and sulfuric acid as catalysts.

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Substitution Positions in Benzene

The relative positions of substituents on a benzene ring, with the 1 position designating the carbon atom where the main functional group is attached.

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Sulfonation

The process of introducing a sulfonic acid group (-SO3H) onto a benzene ring.

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Alkylation of Benzene (Friedel-Crafts)

A type of electrophilic aromatic substitution that introduces an alkyl group (like -CH3 or -C2H5) onto a benzene ring.

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Acylation of Benzene (Friedel-Crafts)

A type of electrophilic aromatic substitution that introduces an acyl group (containing a carbonyl group, C=O) onto a benzene ring.

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Electrophile in Friedel-Crafts

In Friedel-Crafts reactions, the electrophile is a carbocation, a positively charged carbon atom. It is formed by adding an aluminum chloride (AlCl3) catalyst to a halogenoalkane or an acyl chloride.

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Alkylation Mechanism (Friedel-Crafts)

A three-step mechanism that describes the alkylation of benzene, where an alkyl chain is introduced into the benzene ring.

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Modifying Arene Structure

The process of creating new compounds by changing the structure of existing arenes, often involving Friedel-Crafts reactions.

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Benzene's Reactivity

The ability of benzene to undergo electrophilic substitution reactions, where an electrophile replaces a hydrogen atom on the benzene ring.

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Electrophile in Electrophilic Substitution

The molecule that attacks the benzene ring in electrophilic substitution reactions. It is typically a positively charged species.

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Alkylation of benzene

Alkylation of benzene is a reaction where an alkyl group replaces a hydrogen atom on the benzene ring. It is a type of electrophilic aromatic substitution reaction. The product is an alkylbenzene.

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Acylation of benzene

Acylation of benzene is a reaction where an acyl group replaces a hydrogen atom on the benzene ring. It is a type of electrophilic aromatic substitution reaction. The product is an acylbenzene.

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Electrophile in Benzene Reactions

The electrophile is an electron-deficient species that attacks the electron-rich benzene ring in electrophilic aromatic substitution reactions like alkylation and acylation. It is often a carbocation or acylium ion.

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Benzene ring in Reactions

The benzene ring is a cyclic, planar molecule with six carbon atoms and six hydrogen atoms. It has a unique electronic structure that makes it highly reactive to electrophilic attack.

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Catalyst regeneration

In the alkylation and acylation of benzene, the catalyst (usually AlCl3) regenerates itself in the final step. The catalyst is essential for the reaction to proceed, but it is not consumed in the process.

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Oxidation of alkyl side-chain

The alkyl side-chain of an alkylarene, like methylbenzene, can be oxidized using a strong oxidizing agent, e.g., potassium manganate(VII), under reflux conditions. This reaction converts the alkyl side-chain to a carboxylic acid.

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Hydrogenation of benzene

Hydrogenation of benzene is a reaction where the unsaturated benzene ring is converted to the saturated cyclohexane ring. This reaction requires hydrogen gas and a catalyst, typically nickel or platinum.

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Reaction type of benzene hydrogenation

The reaction of benzene or its derivatives with hydrogen gas to form a saturated ring is classified as an addition reaction because the hydrogen atoms are added to the benzene ring, breaking the double bonds, and creating a single bond between each carbon.

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Study Notes

Benzene Ring Structure and Bonding

  • Benzene is a six-carbon atom ring, a crucial functional group in many organic compounds (medicines, dyes, plastics).
  • Kekulé's structure initially proposed three double bonds alternating with single bonds in the ring, but this model fails to reflect benzene's symmetrical and planar structure.
  • Modern understanding reveals benzene's structure as a planar hexagon with all carbon-carbon bonds equal in length. This is due to the delocalisation of π electrons, spreading above and below the plane of the ring.
  • The six π electrons are delocalised, meaning they're not confined to a specific carbon-carbon bond but are shared by all six carbon atoms. Forming a continuous ring of pi bonds.
  • Each carbon atom in benzene is sp² hybridised forming three σ bonds, and one unhybridized p orbital that overlaps with neighbouring carbon atoms to form the delocalized π system.
  • Bond lengths in benzene are intermediate between C-C single and C=C double bonds reflecting the delocalisation of electrons within the ring. (approx. 0.139 nm for C-C bonds)

Naming Aromatic Compounds

  • Aryl compounds include functional groups directly substituted onto a benzene ring, replacing a hydrogen atom.
  • Different substituent groups result in different aryl compounds, with specific naming conventions.

Electrophilic Substitution in Benzene

  • Benzene reacts with electrophiles, which are electron-seeking species, through electrophilic substitution reactions, maintaining the stability of the benzene ring's cyclic π bond structure.
  • Examples of reactants include chlorine, bromine (with aluminium bromide as a catalyst), and the nitration mixture (nitric and sulfuric acids to produce the nitronium ion).
  • The reaction with bromine or chlorine uses a catalyst, typically anhydrous AlBr3 or AlCl3, to generate the electrophile needed for the substitution reaction. 

Friedel-Crafts Reactions: Alkylation and Acylation

  • Friedel-Crafts reactions are electrophilic substitution reactions that add alkyl or acyl groups to a benzene ring.
  • Typical alkylating agents could be a halogenoalkane and a catalyst
  • Typical acylating agents could be acyl chlorides or acid anhydrides with a catalyst, both reactions proceed via a carbocation electrophile.
  • The reactions proceed by forming a carbocation electrophile to attack the benzene ring.

Oxidation of Side Chains in Arenes

  • Oxidation reactions of the alkyl side-chains in aryl compounds are possible, where the alkyl side-chain can be oxidized, transforming them into carboxylic acids (for example, methylbenzene oxidizing to produce benzoic acid)

Hydrogenation of Arenes

  • The hydrogenation of arenes results in the conversion of the benzene ring into a saturated ring compound, in this case cyclohexane, because the hydrogen atoms bond to each carbon atom of the benzene ring to form a saturated alkane chain.

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