Portmess Homework Q&S 109

Portmess Homework Q&S 109 - 103 STRUCTURE AND...

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5.29 ( a ) Carbon atoms that are involved in double bonds are sp 2 -hybridized, with ideal bond angles of 120 ° . Incorporating an sp 2 -hybridized carbon into a three-membered ring leads to more angle strain than incorporation of an sp 3 -hybridized carbon. 1-Methylcyclopropene has two sp 2 - hybridized carbons in a three-membered ring and so has substantially more angle strain than methylenecyclopropane. The higher degree of substitution at the double bond in 1-methylcyclopropene is not suf f cient to offset the increased angle strain, and so 1-methylcyclopropene is less stable than methyl- enecyclopropane. ( b ) 3-Methylcyclopropene has a disubstituted double bond and two sp 2 -hybridized carbons in its three-membered ring. It is the least stable of the isomers. 5.30 In all parts of this exercise, write the structure of the alkyl halide in suf f cient detail to identify the carbon that bears the halogen and the b -carbon atoms that bear at least one hydrogen. These are the carbons that become doubly bonded in the alkene product.
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