levo

Aromaticity

Electrophilic substitution: nitration and halogenation

  • 3 things to know
  • Component 2

Overview

Reaction type characteristic of arenes, intermediate formed when an electrophile bonds to benzene and electrophile in nitration and give the equation for its formation.

What you need to know

Answer each one before you reveal it.

Your recallNot started
Key term

Why is benzene attacked by electron-deficient species rather than by nucleophiles?

Key term

Describe the second step of electrophilic substitution in benzene, saying what the curly arrow moves.

Key term

Which reagents nitrate benzene, and at what temperature is the mixture held?

Questions from this subtopic

Each one with the model answer underneath.

  1. 1

    Name the reaction type characteristic of arenes.

    Model answer

    Electrophilic substitution.

  2. 2

    Why is benzene attacked by electron-deficient species rather than by nucleophiles?

    Model answer

    The delocalised π system forms a region of high electron density above and below the plane of the ring, which attracts anything short of electrons and repels anything carrying a lone pair or negative charge.

  3. 3

    Describe the first step of electrophilic substitution in benzene, saying what each curly arrow moves.

    Model answer

    A curly arrow runs from the delocalised π system of the ring to the electrophile, donating a pair of electrons to form a σ bond between one ring carbon and the electrophile.

  4. 4

    Describe the intermediate formed when an electrophile bonds to benzene.

    Model answer

    It is a positively charged intermediate in which the carbon now bearing the electrophile has become sp³ and has dropped out of the delocalised system, leaving four π electrons spread over the remaining five carbon atoms and a positive charge shared round the ring.

  5. 5

    Describe the second step of electrophilic substitution in benzene, saying what the curly arrow moves.

    Model answer

    A curly arrow runs from the bonding pair of the C—H bond at the substituted carbon back into the ring. The hydrogen leaves as H⁺ and the full delocalised system of six electrons is restored.

  6. 6

    Explain why the intermediate loses H⁺ instead of gaining a negative ion.

    Model answer

    Losing a proton restores the ring of six delocalised electrons and recovers about 152 kJ mol⁻¹ of stability, whereas capturing an anion would leave the delocalisation permanently broken.

Other ways to work this

The same content, four other ways.

What is inside Levo

Six ways to work the same material.

1Closed book
2Open book
3Closed book

The 3-step method, run for you

Answer cold, learn it, then prove it stuck. Levo tracks the jump between your first attempt and your last.

Formulae and Equations
Basic Ideas About Atoms
Chemical Calculations
Bonding

Cram a whole paper in one sitting

Sort every topic into what you know and what you do not, then drill only the weak ones.

An is formed.
alkenealcoholaldehyde

Blank Blitz makes facts automatic

Rapid timed gap-fills on the terms and numbers you need to recall without thinking.

AThe equation is k = A exp(−Ea/RT).
BHere k is the rate constant.
CA is the pre-exponential factor.

Build It gets the exam shape right

Assemble a full-mark answer from its marking points, in the order an examiner wants them.

Kc is a fixed number at a given temperature.
TrueFalse

Test It catches misconceptions

Spot the fault in a statement. The traps are the mistakes students actually make.

721941163128510

Brain Breaks between sessions

Short focus games to reset attention, so the next set lands better than the last.

Every question in Aromaticity, on a schedule.

Attempt a question from memory, write the correct version, then attempt it again. Levo records the jump between your first attempt and your last, and brings each question back on the day you are due to forget it.

Or £46 a year, about £3.83 a month. Cancel anytime.