Question

CHEM 8A (F Substitution & ation acoS tie product 9 Step reactou tu E 3. You and your labmate both need to make the chiral alkene shown below. You used the cis alcohol as a reactant, and your labmate used the trans alcohol. You both characterized your products, but the characterization tells you that you obtained a different product than your labmate. Who made the correct product? What incorrect product formed instead? Explain why by proposing a mechanism that shows the formation of the different products. Cis OH fians 1) TsCI, pyridine 2) NaOH OH or Both of you purified your compound by column chromatography because of the presence of a product (more polar). What was the minor product? Propose a mechanism that shows the forma the minor product.

Answer 1

9048 Cin Ta-C) I cHz Gis isomer н . - GOOD of leaving gooupe In cis isomer, leaving group and abstracring H. are anti periplango to each other & hence cagy foo eliminacion gedchon. According to Zaitsev's owe , mode substituted alkéne formed as a major product: Ht absoaching hydron > OTG He OH CH3 YMI ON In this case, Ho is anti periplanar to leaving gooup and not Ha. TC) Ру