Dolbier HW Solutions 254

Dolbier HW Solutions 254 - Diels Alder reaction. 10.38 ( a...

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10.36 To predict the constitution of the Diels Alder adducts, we can ignore the substituents and simply remember that the fundamental process is ( a ) ( b ) ( c ) 10.37 The carbon skeleton of dicyclopentadiene must be the same as that of its hydrogenation product, and dicyclopentadiene must contain two double bonds, since 2 mol of hydrogen are consumed in its hydrogenation . The molecular formula of dicyclopentadiene (C 10 H 12 ) is twice that of 1,3-cyclopentadiene (C 5 H 6 ), and its carbon skeleton suggests that 1,3-cyclopentadiene is undergoing a Diels Alder reac- tion with itself. Therefore: One molecule of 1,3-cyclopentadiene acts as the diene, and the other acts as the dienophile in this
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Unformatted text preview: Diels Alder reaction. 10.38 ( a ) Since allyl cation is positively charged, examine the process in which electrons f ow from the HOMO of ethylene to the LUMO of allyl cation. LUMO HOMO Antibonding Bonding 1 C 5 H 6 C 5 H 6 Dicyclopentadiene C 10 H 12 C 10 H 16 2H 2 Pt (C 10 H 12 C 10 H 16 ) 1 NO 2 H NO 2 CH 2 OCH 3 CH 3 OCH 2 1 C CO 2 CH 3 CO 2 CH 3 CO 2 CH 3 CO 2 CH 3 C O O OCH 3 1 C CO 2 CH 3 CO 2 CH 3 CO 2 CH 3 CO 2 CH 3 C (CH 3 ) 3 SiO OCH 3 (CH 3 ) 3 SiO 248 CONJUGATION IN ALKADIENES AND ALLYLIC SYSTEMS...
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