By C.H. Bamford
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Extra resources for Addition and Elimination Reactions of Aliphatic Compounds
The alternative hypothesis, that the reagent, product, or catalyst complexes with the olefin in a rapid pre-equilibrium sequence and that this complex is then more susceptible to attack by the reactant, viz. 1 I ) does not seem to have been considered. An analogous suggestion has been made to explain high orders with respect to halogen in the addition of bromine to olefins"". 4 E L E C T R O P H I L I C N I T R O G E N Electrophilic nitrogen, in the forms of NO,+, NO+, or ArN,+, has been well authenticated in aromatic substitution.
As a result, t h e appropriate, more complex kinetic equation is required to allow for the equilibrium position of the reaction, or else a large excess of the olefin is used to drive the reaction substantially to completion. In solvents of low polarity (carbon disulphide, carbon tetrachloride) the reaction is of high order with respect to iodine. 4) to be dominant. In nitrobenzene or acetic acid, however, the reaction showed second-order dependence upon the halogen concentrationg1,viz. The present trend is towards a mechanism involving solvent polarisation of the halogen molecule prior to reaction (either by bulk solvent or by other halogen molecules) but the mechanism is by no means firmly decided.
6 z U -. 8 x 10-3 60 krtslktransaddn. e rA -1 m K rA - 4-X-I-Butenes ? 75 -r! 5-X- I -Pcntenes x = c1 X = Br X=l X = OMe X = OCOCF, X = OCOCH, 74 74 . 74 74 74 k1 = 1 . 64 x 10-5 Catalyst % Reaciion Time AH$ (sec) (kcalmole-') -AS$ (eu) Ref. 8 109kl = 8 . 7 b 1 . 3 79 79 4 0 w a 9 2 X = m-Me 5 2 P ? O 79 79 79 79 79 79 79 79 79 79 79 79 79 79 79 79' 79 79 79 79 79 79 79 79 79 79 79 79 79 79 79 79 79 79 > U El r! 08 X lo-, ("c) 40 40 40 P % T Solvent Catalyst Reaction Time AH* -AS* (see) (keaLrnole-') (eu) HOAc HOAc HOAc Ref.
Addition and Elimination Reactions of Aliphatic Compounds by C.H. Bamford