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Portmess Homework Q&S 99

Portmess Homework Q&S 99 - 93 STRUCTURE AND...

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5.8 The most stable C 6 H 12 alkene has a tetrasubstituted double bond: 5.9 Apply the two general rules for alkene stability to rank these compounds. First, more highly substi- tuted double bonds are more stable than less substituted ones. Second, when two double bonds are similarly constituted, the trans stereoisomer is more stable than the cis. The predicted order of de- creasing stability is therefore: 5.10 Begin by writing the structural formula corresponding to the IUPAC name given in the problem. A bond-line depiction is useful here. The alkene is extremely crowded and destabilized by van der Waals strain. Bulky tert -butyl groups are cis to one another on each side of the double bond. Highly strained compounds are often quite dif fi cult to synthesize, and this alkene is a good example. 5.11 Use the zigzag arrangement of bonds in the parent skeleton fi gure to place E and Z bonds as appro- priate for each part of the problem. From the sample solution to parts (
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