Search results
Results from the WOW.Com Content Network
Figure 5 shows 2-chloro-2,3-dimethylbutane in a sawhorse projection with chlorine and a hydrogen anti-periplanar to each other. Syn-periplanar or synperiplanar is similar to anti-periplanar. In the syn-periplanar conformer, the A and D are on the same side of the plane of the bond, with the dihedral angle of A−B and C−D between +30° and ...
This is because 2-chlorobutane possesses two different sets of β-hydrogens at the first and third carbons respectively, resulting in 1-butene or 2-butene. It is important to note that as a secondary alkyl halide, both E2 and Sn2 reactions are equally likely when reacting with a substance that can act as both a base and a nucleophile.
One consequence of this analysis is that trans-4-tert-butylcyclohexyl chloride cannot easily eliminate but instead undergoes substitution (see diagram below) because the most stable conformation has the bulky t-Bu group in the equatorial position, therefore the chloride group is not antiperiplanar with any vicinal hydrogen (it is gauche to all ...
The gauche effect is very sensitive to solvent effects, due to the large difference in polarity between the two conformers.For example, 2,3-dinitro-2,3-dimethylbutane, which in the solid state exists only in the gauche conformation, prefers the gauche conformer in benzene solution by a ratio of 79:21, but in carbon tetrachloride, it prefers the anti conformer by a ratio of 58:42. [9]
In stereochemistry, the Klyne–Prelog system (named for William Klyne and Vladimir Prelog) for describing conformations about a single bond offers a more systematic means to unambiguously name complex structures, where the torsional or dihedral angles are not found to occur in 60° increments. [1]
A secondary deuterium isotope effect of slightly larger than 1 (commonly 1 - 1.5) is observed. There is no antiperiplanar requirement. An example is the pyrolysis of a certain sulfonate ester of menthol: E1 elimination Nash 2008, antiperiplanar relationship in blue Only reaction product A results from antiperiplanar
This page was last edited on 2 December 2021, at 15:39 (UTC).; Text is available under the Creative Commons Attribution-ShareAlike 4.0 License; additional terms may apply.
A: antiperiplanar, anti or trans. B: synclinal or gauche. C: anticlinal or eclipsed. D: synperiplanar or cis. [2] Rotating their carbon–carbon bonds, the molecules ethane and propane have three local energy minima. They are structurally and energetically equivalent, and are called the staggered conformers.