Portmess Homework Q&S 108

Portmess Homework Q&S 108 - 102 STRUCTURE AND...

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( d )( Z )-4,4-Dimethyl-2-pentene; 4650 kJ/mol (1111.4 kcal/mol). Disubsti- tuted double bond, but destabilized by van der Waals strain. ( b ) 2,4-Dimethyl-1-pentene; 4638 kJ/mol (1108.6 kcal/mol). Disubstituted double bond. ( c ) 2,4-Dimethyl-2-pentene; 4632 kJ/mol (1107.1 kcal/mol). Trisubstituted double bond. 5.28 ( a ) 1-Methylcyclohexene is more stable; it contains a trisubstituted double bond, whereas 3-methylcyclohexene has only a disubstituted double bond. ( b ) Both isopropenyl and allyl are three-carbon alkenyl groups: isopropenyl is CH 2 ? CCH 3 , allyl is CH 2 ? CHCH 2 @ . g Isopropenylcyclopentane has a disubstituted double bond and so is predicted to be more sta- ble than allylcyclopentane, in which the double bond is monosubstituted. ( c ) A double bond in a six-membered ring is less strained than a double bond in a four-membered ring; therefore bicyclo[4.2.0]oct-3-ene is more stable.
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