Question

The compound below undergoes E2 elimination using LDA as a strong base, and there is only one observed product.

1. Draw the observed product and the theoretically possible isomer that we don’t see.

2. Draw the mechanism to produce both.

3. Draw an energy coordinate diagram for this reaction including the two low

   energy conformations of the starting material (hint: chairs), the observed product, and the theoretically possible product. Make sure all relative energies are accurate (ground state and transition state).

4. Explain why we only get one product, referencing the energy diagram and pictures from above.

LDA, THF Br only observed product theoretically possible regioisomeric product, not observed

Answer 1

According to ge'ven condition the product is Sumer LOA THE 8 + Ğ only obserwe, Thoritically l product possible regionso LDA=) Lithium di isopropyle Athilum de isopropyle . meric product. amide, hulke he - attack not obserne through less linder side E2 reaction is a one step bimolecular elimination reaction, which is shown below. mechanism ( for 1st produe (for 1st product) 8 LDA YH--LDA obsome - Bulky base product. attack through less Transition state Rinder side mechanism (for and product) sa Vente en or LOA > S ner → Transition state . Not observe here, and product not observe because eliminating and acidie it atom present in side and also .LOA is bulky base, so, not attack through mare hinder side. so, product highy energetic Yo Highly energetic (not possible) not possible, Energy 1 El blow energetice Lucent possible repetont - product-2 e product-1. - Reaction co-ordinate