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For 1,2- and 1,4-disubstituted cyclohexanes, a cis configuration leads to one axial and one equatorial group. Such species undergo rapid, degenerate chair flipping. For 1,2- and 1,4-disubstituted cyclohexane, a trans configuration, the diaxial conformation is
The molecular motions involved in a chair flip are detailed in the figure on the right: The half-chair conformation (D, 10.8 kcal/mol, C 2 symmetry) is the energy maximum when proceeding from the chair conformer (A, 0 kcal/mol reference, D 3d symmetry) to the higher energy twist-boat conformer (B, 5.5 kcal/mol, D 2 symmetry). The boat ...
The chair conformation is the favored configuration, because in this conformation, the steric strain, eclipsing strain, and angle strain that are otherwise possible are minimized. [4] Which of the possible chair conformations predominate in cyclohexanes bearing one or more substituents depends on the substituents, and where they are located on ...
The dashed lines indicate 6-atom interactions found in this conformation of ethyl cyclohexane, which amounts to approximately 2.7 kcal/mol (11 kJ/mol) in the enthalpic term of Free Energy. The dashed lines here signify the 7 atom interactions, which contribute approximately 8 kcal/mol (33 kJ/mol) to the enthalpic term making this conformation ...
English: Chair (left) and boat (right) conformation of a general cyclohexane structure (a = axial substituent, e = equatorial substituent) Date: 26 June 2010: Source ...
The staggered conformation is more stable by 12.5 kJ/mol than the eclipsed conformation, which is the energy maximum for ethane. In the eclipsed conformation the torsional angle is minimised. staggered conformation left, eclipsed conformation right in Newman projection
The most stable position of a cyclohexane would be the "chair-position". But if the cyclohexane has 2 or more t-butyl groups off the 1 and 4 position then the boat position is the best due to the avoidance of steric interference. Remember: more stable means less potential energy (it won't blow up on you)!
The reaction conducted in two steps beginning with the conversion of DMT to the diester dimethyl 1,4-cyclohexanedicarboxylate (DMCD): C 6 H 4 (CO 2 CH 3) 2 + 3 H 2 → C 6 H 10 (CO 2 CH 3) 2. In the second step DMCD is further hydrogenated to CHDM: C 6 H 10 (CO 2 CH 3) 2 + 4 H 2 → C 6 H 10 (CH 2 OH) 2 + 2 CH 3 OH. A copper chromite catalyst ...