Dolbier HW Solutions 241

Dolbier HW Solutions 241 - 235 CONJUGATION IN ALKADIENES...

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10.11 The two double bonds of 2-methyl-1,3-butadiene are not equivalent, and so two different products of direct addition are possible, along with one conjugate addition product. 10.12 The molecular formula of the product, C 10 H 9 ClO 2 , is that of a 1:1 Diels Alder adduct between 2-chloro-1,3-butadiene and benzoquinone. 10.13 Unravel the Diels Alder adduct as described in the sample solution to part ( a ). ( b ) ( c ) 10.14 Two stereoisomeric Diels Alder adducts are possible from the reaction of 1,3-cyclopentadiene and methyl acrylate. In one stereoisomer the CO 2 CH 3 group is syn to the bridge, and is called the endo isomer. In the other stereoisomer the CO 2 CH 3 group is anti to the bridge and is called the exo isomer. 1 1,3-Cyclopentadiene 1 O OCH 3 C H Endo isomer (75%) O OCH
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