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The tert-butyl lock template
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cis- and trans-4-tert-butylcyclohexanol: the tert-butyl group stays equatorial (A-value about 20 kJ mol⁻¹), locking the OH equatorial (trans) or axial (cis).
What the template shows
- C(CH₃)₃ is far too big to sit axial, so it fixes the chair: other groups are locked axial or equatorial
- 4-tert-Butylcyclohexanol
- trans-4-tert-butylcyclohexanol
- C(CH₃)₃ equatorial, OH equatorial
- cis-4-tert-butylcyclohexanol
- C(CH₃)₃ equatorial, OH axial
- An axial tert-butyl group would clash badly with the axial H on C3 and C5 (A-value about 20 kJ mol⁻¹): more than 99.9 % of molecules keep it equatorial.
- The ring no longer flips in practice, so each diastereomer has one chair: trans has OH equatorial, cis has OH axial.
- Locked rings let axial and equatorial groups be compared directly: an axial OH is more hindered, is oxidised faster (strain relief) and is esterified more slowly.
- The same idea is used to fix conformations in the study of E2 eliminations (an anti-periplanar, diaxial H and leaving group).
- Wedge = toward you, hash = away from you · every part of this figure is editable
Drawn with 22 atoms, 19 shapes – every one editable in MolDraw.
Sources
How to use this template
- Press Edit in MolDraw. The template opens on the canvas of the free MolDraw editor.
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Frequently asked questions
Is the The tert-butyl lock template free?
You can preview the The tert-butyl lock template here and open and edit it in MolDraw for free. Downloading or exporting it is part of MolDraw Pro, together with the other premium templates.
Can I edit the The tert-butyl lock template?
Yes. It opens as an ordinary MolDraw drawing, so every structure, arrow, label and colour can be changed, and you can add your own content around it.
Is the chemistry checked?
Every structure is checked with RDKit and every curly arrow passes MolDraw’s electron-flow audit. The sources used are listed on this page.
Are the R/S labels in the stereochemistry templates checked?
Yes. Every R/S and E/Z descriptor is computed with RDKit from the drawn structure, so the labels match the wedges and dashes.