Octet

Octet / Reactions

Diels-Alder Reaction

Diels-Alder Reaction (Pericyclic.) Converts C=CC=C.C=C to C1CC=CCC1 using Heat (or Lewis acid catalyst). Conditions: Heat or pressure. Stereochemistry: Syn addition on both components. Endo product kinetically favored..

Pericyclic

Reaction details

Name

Diels-Alder Reaction

Type

Pericyclic

Starting Material

C=CC=C.C=C

Product

C1CC=CCC1

Reagents

  • Heat (or Lewis acid catalyst)

Conditions

Heat or pressure

Mechanism
  1. Smiles

    C=CC=C

    Description

    Diene (1,3-butadiene) in s-cis conformation

  2. Smiles

    C=C

    Description

    Dienophile (ethene)

  3. Smiles

    C1CC=CCC1

    Description

    Cyclohexene (6-membered ring formed)

Stereochemistry

Syn addition on both components. Endo product kinetically favored.

Tips

  1. [4+2] cycloaddition - concerted, no intermediates

  2. Electron-rich diene + electron-poor dienophile = faster

  3. Diene must be in s-cis conformation

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Reactions

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Source collection

SN2 with Hydroxide

SN2 with Hydroxide (SN2 Substitution.) Converts CCBr to CCO using NaOH, KOH. Conditions: Polar aprotic solvent in DMSO, DMF, or acetone. Stereochemistry: Inversion of configuration (Walden inversion).

Substitution

SN2 with Cyanide

SN2 with Cyanide (SN2 Substitution.) Converts CCI to CC#N using NaCN, KCN. Conditions: Polar aprotic solvent in DMSO or DMF. Stereochemistry: Inversion of configuration.

Substitution

SN1 Solvolysis

SN1 Solvolysis (SN1 Substitution.) Converts CC(C)(C)Br to CC(C)(C)O using H₂O. Conditions: Polar protic solvent, heat in Water or aqueous ethanol. Stereochemistry: Loss of stereocontrol (planar carbocation attacked from either face → racemization if chiral ce...

Substitution

SN2 with Tosylate Leaving Group

SN2 with Tosylate Leaving Group (SN2 Substitution.) Converts CCOS(=O)(=O)c1ccc(C)cc1 to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

SN2 with Azide

SN2 with Azide (SN2 Substitution.) Converts CCBr to CCN=[N+]=[N-] using NaN₃. Conditions: Polar aprotic solvent.

Substitution

E2 Elimination

E2 Elimination (E2 Elimination.) Converts CC(Br)CC to CC=CC using 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..

Elimination

Study guides

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