Benzene and Aromatic Compounds Lecture Quiz
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Questions and Answers

Which of the following is true about benzene?

  • It is a non-cyclic compound
  • It has four structural criteria for aromaticity
  • It is the simplest aromatic hydrocarbon (correct)
  • It undergoes addition reactions similar to other highly unsaturated compounds

What did August Kekulé propose about benzene's structure?

  • It has only one Kekulé structure
  • It contains two compounds, each with a six-membered ring and three alternating Ï€ bonds (correct)
  • It has a non-planar structure
  • It contains a single compound with a six-membered ring

How many π electrons does benzene have?

  • Eight
  • Four
  • Three
  • Six (correct)

What are the criteria for a compound to be aromatic, according to Hückel’s Rule?

<p>It must have aligned p orbitals for delocalization of π electron density (D)</p> Signup and view all the answers

What happens when benzene reacts with Br2 in the presence of a Lewis acid?

<p>It retains the benzene ring (C)</p> Signup and view all the answers

How many stereoisomers are possible for the given structure?

<p>8 (B)</p> Signup and view all the answers

What is the effect of a plane of symmetry on a meso compound?

<p>It makes the compound achiral (D)</p> Signup and view all the answers

What is the priority rule based on when assigning priorities to atoms bonded to chiral centers?

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

What system is used for naming enantiomers based on their absolute configuration?

<p>Cahn-Ingold-Prelog system (A)</p> Signup and view all the answers

What is the total number of substituents that should be identified when naming chiral centers?

<p>4 (C)</p> Signup and view all the answers

What is the maximum number of stereoisomers possible when a compound has 4 stereocenters?

<p>32 stereoisomers (B)</p> Signup and view all the answers

How many stereoisomers are possible for the given structure?

<p>8 stereoisomers (D)</p> Signup and view all the answers

What is the effect of a plane of symmetry on a meso compound?

<p>It makes the compound achiral (C)</p> Signup and view all the answers

What system is used for naming enantiomers based on their absolute configuration?

<p>Cahn-Ingold-Prelog System (C)</p> Signup and view all the answers

What happens when benzene reacts with Br2 in the presence of a Lewis acid?

<p>Substitution of one H atom with Br (C)</p> Signup and view all the answers

Flashcards

What is benzene?

Benzene is the simplest aromatic hydrocarbon, meaning it has a ring structure with delocalized electrons.

What did Kekulé propose about benzene?

August Kekulé proposed that benzene's structure consists of two compounds. Each has a six-membered ring and three alternating π bonds.

How many π electrons does benzene have?

Benzene has six π electrons, which are delocalized throughout the ring.

What is Hückel's Rule regarding aromaticity?

Hückel's Rule defines a compound as aromatic if it has a cyclic system of p orbitals, containing a total of (4n + 2) π electrons, where n is a non-negative integer.

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What happens when benzene reacts with bromine?

When benzene reacts with Br2 in the presence of a Lewis acid, it undergoes electrophilic aromatic substitution. The benzene ring remains intact, but one hydrogen atom is replaced by a bromine atom.

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What does a plane of symmetry do to a meso compound?

A plane of symmetry divides a molecule into two identical halves, making it achiral. A meso compound is achiral because it possesses a plane of symmetry, despite having chiral centers.

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What are the priority rules for chiral centers?

The priority rule in assigning priorities to atoms bonded to chiral centers is based on the atomic number. Higher atomic number gets higher priority

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How are enantiomers named based on their configuration?

The Cahn-Ingold-Prelog (CIP) system is used to assign absolute configurations to chiral centers. It involves assigning R or S to each chiral center based on priority rankings.

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What should you consider when naming chiral centers?

To name a chiral center, you need to identify four substituents attached to it, each of which has a different priority.

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How many stereoisomers are possible with 4 stereocenters?

The maximum number of stereoisomers possible for a compound with 4 stereocenters is 2^n, where n is the number of stereocenters. So, for 4 stereocenters, the maximum is 2^4, which equals 16.

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How many stereoisomers are possible for a given structure?

The number of possible stereoisomers depends on the number of stereocenters present in the molecule. For a given structure with specific stereocenters, the number of possible stereoisomers can be calculated based on the number of stereocenters.

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What does a plane of symmetry do?

A plane of symmetry divides a molecule into two identical halves, making it achiral. A meso compound is achiral because it possesses a plane of symmetry, despite having chiral centers.

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What is the CIP system?

The Cahn-Ingold-Prelog (CIP) system is used to assign absolute configurations to chiral centers. It involves assigning R or S to each chiral center based on priority rankings.

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What happens when benzene reacts with bromine in the presence of a Lewis acid?

When benzene reacts with Br2 in the presence of a Lewis acid, it undergoes electrophilic aromatic substitution. The benzene ring remains intact, but one hydrogen atom is replaced by a bromine atom.

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Study Notes

Benzene Structure and Properties

  • August Kekulé proposed a hexagonal, planar structure for benzene.
  • Benzene has 6 Ï€ electrons.

Aromatic Compounds

  • According to Hückel's Rule, a compound must have 4n + 2 Ï€ electrons, where n is an integer, to be aromatic.
  • Aromatic compounds must also be planar and have a continuous ring of p orbitals.

Electrophilic Substitution Reaction

  • When benzene reacts with Br2 in the presence of a Lewis acid, an electrophilic substitution reaction occurs, resulting in a bromine atom substituting for a hydrogen atom on the benzene ring.

Stereochemistry

  • A plane of symmetry in a meso compound makes it achiral, meaning it does not exhibit optical activity.
  • The priority rule for assigning priorities to atoms bonded to chiral centers is based on atomic number.
  • The R/S system is used for naming enantiomers based on their absolute configuration.
  • When naming chiral centers, four substituents should be identified.
  • The maximum number of stereoisomers possible for a compound with 4 stereocenters is 2^4 = 16.

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Test your knowledge of benzene and aromatic compounds with this lecture quiz. Explore the structure and properties of benzene, and learn about August Kekulé's proposal regarding the structure of benzene.

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