Question

1. Starting from the beta-keto thioester we created in lecture, take us to the next step, the beta- hydroxy thioester. NADH NAD 2. a. In the problem above, what role did NADH play? Select one: (oxidant, reductant, neither) b. What happened to the beta-keto thioester? [reduced, oxidized, dehydrated] 3. With the beta hydroxy thioester in hand, the next step is a dehydration. Two mechanisms can be drawn for this. Give each a shot. HH H, SCOA HO HC H20 enol assisted elimination HC SCOA SCOA

Truly all of them, Due to school closures Lectures have been difficult

Answer 1

The reaction mechanism for the synthetic sequences from the question 1 to 6 have been completed and the detail are explained as below.

PAGE NO: DATE: SCA Reduction DALLA scot Ř NADA 2a in the above reduction reaction the role IG NADH is playing as reducing agent - reductant ab. dhe B-keto thioestor reduced into to B hydroxy thicester The B-hydroxy thioester undergo two types la elimination reactions (1) E2 and 2) end assisted elimination to give alpha beta unsaturated thioester.product as below. SA E2 cal ScoA Base (8.) SCOA product

E NO SCOA B- Taubomenism End | End assisted -H20 elimination SCA Product Reduction of X, B- unsaturated this ester product using NADH. - R 1,4-roverson b scoa 4 Endate Scan Tauto Tautomerism SCOA Keto from stable

Reaction mechanism of zingerone from Gingerol = Rebosynthesis WA ACO Holy porn onged binderd End. U protonated aloelige Zingerone Thus retosynthesis of Gingerd give the two synthones do Zingerore and hexane-aldehyde. The Alool condensation using two plasting material would give back the Gingerd.

DATE: 6. Reaching mechanism of shogoal. London bingrad. Bil And formation je Delayaranting to hydration Stimmation shagen +40 Botha