Octet

Octet / Reactions

Friedel-Crafts Alkylation

Friedel-Crafts Alkylation (Electrophilic Aromatic Substitution Aromatic). Starts from Benzene with (CH₃)₂CHCl, AlCl₃. Mechanism in 3 steps.

Aromatic

Reaction details

Name

Friedel-Crafts Alkylation

Type

Aromatic

Subtype

Electrophilic Aromatic Substitution

Starting Material

c1ccccc1

Product

c1ccccc1C(C)C

Reagents

  • (CH₃)₂CHCl

  • AlCl₃

Mechanism
  1. Smiles

    c1ccccc1

    Description

    Benzene

  2. Smiles

    c1ccccc1

    Description

    AlCl₃ + RCl → R⁺ (carbocation)

  3. Smiles

    c1ccccc1C(C)C

    Description

    Isopropylbenzene (cumene)

Tips

  1. Carbocation can rearrange!

  2. Product more reactive than starting material → polyalkylation

  3. Does NOT work on deactivated rings (nitrobenzene)

  4. AlCl₃ catalyst

Related Reactions

  • friedel-crafts-acylation

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Reactions

Related Content

Reagents, conditions, stereochemistry and mechanism.

SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution). Starts from Bromoethane with NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion). Mechanism in 3 steps.

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution). Starts from Iodoethane with NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration. Mechanism in 3 steps.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution). Starts from Tertiary bromide with H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral center)...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution). Starts from Ethyl tosylate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution). Starts from Alkyl bromide substrate with NaN₃. Conditions: Polar aprotic solvent. Mechanism in 2 steps.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination). Starts from 2-Bromobutane with KOtBu, NaOEt, NaOH (conc.). Conditions: Strong base, heat in t-BuOH or EtOH. Stereochemistry: Anti-periplanar geometry required. E/Z depends on which H is removed.. Mechanism in 3 steps.

Elimination

Study guides

Related study guides

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Arrow-pushing basicsSN1 vs SN2 decision guideStudy reactions without memorizingAll guides