.icleau g 226-240 TroM Carey, Organic Chemistry from Carey, Organic C 2. Problem
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.icleau g 226-240 TroM Carey, Organic Chemistry from Carey, Organic C 2. Problems from Carey: none Although anti geometry is preferred for E2 reactions, it isn't absolutely necessary. The deuterated bromo compound shown here reacts with strong base to yield an undeuterated alkene. Clearly, a syn elimination has occurred. Make a molecular model of the starting material to examine its geometry, and then explain the result. 3. Br id nave not In light of your answer to Problem 3, account for the observation that one of the following isomers undergoes E2 reaction approximately 100 times as fast as the other. Which isomer is the more reactive, and why? 4 Cl RO- Cl RO Ethers can often be prepared by Sy2 reaction of alkoxide ions with alky] halides.Explanation / Answer
3. In this locked conformation as we can see, the bromo and D, which are syn to each other are almost parallel to each other. So syn elimination takes place easily, so that resulting p orbitals remain parallel to each other after the elimination resulting in favorable pi bond formation.
4. As we could see in question number 3, syn elimination was favored over anti elimination, though both were possible, since in anti position the H and Br were not anti parallel to each other and thus not lead to effective overlap of p orbitals to form pi bond. So (a) will be 100 times faster than (b) due to better alignment of orbitals parallely to form pi bond.
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