By C.H. Bamford
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Additional info for Addition and Elimination Reactions of Aliphatic Compounds
H,S04aq. H,SO,aq. H,SO,aq. H,S04aq. 66 X a 30 30 30 30 30 30 For truns addition of DBr. For cis addition of DBr. Derived from quoted rate coefficients. From the parameters in Table 111, ref. 99h,1-1R at 25°C. -d [CzH4]/dt = k,[C,H,] +constant. k , does not vary linearly with any acidity function; see however, refs. 83 and 84. 6) For higher reaction orders, the overall order will be indicated by the subscript to the rate coefficient, and the detailed kinetic equation will be shown in a footnote.
Rcft,wiiws p p . 80-86 48 ELECTROPHlLlC A D D I T I O N S TO U N S A T U R A T E D SYSTEMS be well established. T h e reaction has been studied in acetonitrile, and involves addition of the diazonium ion across the olefinic bond to form (where distinction is possible) the more stable carbonium ion; this then undergoes hydrolytic cleavage to form a ketone and a 2,4-dinitrophenylhydrazoneof another carbonyl fragment*75,viz. NHAr + O=C( The order of reactivity Me,C=CMe, > Me,C=CHMe and the sequence PhC(Me)=CH, > PhCH=CHMe < PhCH=CH, indicates that the ratedetermining stage is assisted by electron-donating groups.
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. 8 x 10-5 2,4-Mg-l-pentene k, = 1 . 42 x 10-4 X = 1 2 .