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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.
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 ...
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]
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[1] [3] [4] The ring-flip of substituted cyclohexanes constitutes a common form of conformers. [5] The study of the energetics of bond rotation is referred to as conformational analysis. [6] In some cases, conformational analysis can be used to predict and explain product selectivity, mechanisms, and rates of reactions. [7]
H 2 C=CH 2 + HCl → CH 3 CH 2 Cl. In oxychlorination, hydrogen chloride instead of the more expensive chlorine is used for the same purpose: CH 2 =CH 2 + 2 HCl + 1 ⁄ 2 O 2 → ClCH 2 CH 2 Cl + H 2 O. Secondary and tertiary alcohols react with hydrogen chloride to give the corresponding chlorides.
The stereoelectronic effect affecting the outcome of the facial selectivity of the diene in the Diels–Alder reaction is the interaction between the σ(C(sp 2)–CH 3) (when σ(C(sp 2)–X) is a better acceptor than a donor) or σ(C(sp 2)–X) (when σ(C(sp 2)–X) is a better donor than an acceptor) and the σ* orbital of the forming bond ...
One is that lithium is antiperiplanar to the C=C bond (blue colored), leading to the conformation of Z C-N; the other one is that lithium and the C=C bond are at the same side of the C-N bond (red colored), leading to the E C-N conformer. There are also two available orientations for the chelating nitrogen and R 2 group, being either E C=C or Z ...