ORG-19

Diels–Alder K snapshot

K = [adduct] / ([diene][dienophile]). Cycloaddition equilibrium.

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EquilibriaDiels–Alder

Governing equation

K=[\mathrm{adduct}]/([\mathrm{diene}][\mathrm{dienophile}])

where

[adduct]: Adduct (mol/L)
[diene]: Diene (mol/L)
[dienophile]: Dienophile (mol/L)
K: Equilibrium K (L/mol)

Lecture brief

Historical brief

Hammett (1937) and Taft linear free-energy, E-factor green metrics, Woodward–Fieser UV and Claisen equilibria are how organic chemistry became predictive. The lab is substituent, waste and tautomer. This sheet (ORG-19 — Diels–Alder K snapshot) is the form associated with Diels–Alder. Working symbols: $[adduct]$ , $[diene]$ , $[dienophile]$ $\rightarrow$ $K$ . A pericyclic 6-electron process. Electron-rich dienes and electron-poor dienophiles give large K.

Purpose

Purpose: compute

K

from

[adduct]

[diene]

[dienophile]

in Organic chemistry via

K=[\mathrm{adduct}]/([\mathrm{diene}][\mathrm{dienophile}])

K = [adduct] / ([diene][dienophile]). Cycloaddition equilibrium. Use it when a real organic chemistry question must be answered in SI before a code check.

Live realistic example

In symbols

Live case. Given

[adduct] = 0.080\,\mathrm{mol/L}

[diene] = 0.020\,\mathrm{mol/L}

[dienophile] = 0.020\,\mathrm{mol/L}

, the governing relation

K=[\mathrm{adduct}]/([\mathrm{diene}][\mathrm{dienophile}])

yields

K = 200.000\,\mathrm{L/mol}

. 1:1 cycloaddition, concentrations of the three species. Move a slider: the numbers are this situation, not a canned story.

Calculator

Inputs

Adduct [adduct]0.08 mol/LDiene [diene]0.02 mol/LDienophile [dienophile]0.02 mol/L

Outputs

Equilibrium K K200.000 L/mol

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Narration of this film

1:1 cycloaddition, concentrations of the three species.

A pericyclic 6-electron process. Electron-rich dienes and electron-poor dienophiles give large K.

Reading speed

Watch on YouTube