Question

Propose multi-step chemical syntheses for the product on the right from the starting material provided, they require more than one step. You can use any reagent with up to four carbons. Show the product for each step in your synthesis. 5. 110 points] Chose TWO of the following transformations and propose multi-step chemical syntheses for the product on the right from the starting material provided. All syntheses require more than one step. You can use any reagent with up to tour carbons. Show the product for each step in your synthesis. HO a) O. b) c)

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Answer #1

5. Synhtetic schemes below

(a) Is prepared by oxidation of alcohol, protection by 1,2-dithiol and deprotection of other carbonyl. Coupling with grignard gives the product.

(b) Is prepared by free radical bromination, followed by hydrolysis and oxidation. alpha-alkylation and then aldol type reaction gives the product.

(c) Is prepared by 3 moles of benzene alkylated and oxidized to acid. esterification with glycerol yields the product.

он PCC HS(CH2)2SH EtMgBr HO он PCC LDA hv aq BrCH2CH2COCH3 NaOH H2O,heat COOH HO OH 1. CHjCI,AICI 2. alk.KMno он (c)3

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