Unformatted text preview: d) There is only 1,2-adduct possible in this reaction. e) There is only 1,4-adduct possible in this reaction. 22. (2 pts) How many isomers, including stereoisomers, form in this reaction? a) 2 b) 4 c) 6 d) 8 e) 16 D-Cl D D Cl Cl D D Cl Cl 1,2-1,4-Comments: This question is about conjugate addition. A simple drawing of the two resonance structures of the allylic cation is all that is needed to draw the products. As can be seen the 1,2- and 1,4- adducts are the same, except for the isotopic substitution. Since the deuteration (addition of D + ) can happen from either face of the ring, and the addition of Cl – to the planar carbocation can also happen from both faces, all stereochemical outcomes are possible on both chiral centers in each adduct, giving 8 total isomers. Similar problems include: PE4A: 8 and homework 14.26. Counting isomers (including stereoisomers) is standard on our exam)....
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- Fall '07
- Psychology, Isotope, 2 pts, 4 pts, major organic product, isotopic substitution, 1,4- adducts