Question

10. What is the final product of the following series of reactions? elom up IN OH 1. HC 2. NaOE OH 1. H,SO Heat 2. Br d Uvdw x toyosn 1 BH, THF 2. H,O2, NaOE 1. MCPBA 2. H,S 3. H,SO, Heat 4. O 5. DMS o lworl bib gboe0 yoM bolyroao OH f ubong ibe 1. NaOE 2. HBr J- 3. Br, H2O 4. H,SO Heat 2

Answer 1

H2CH3 H3 CH3 H3c . 1 HCI 139 CH31) HCI H z cu 2) NaoEt H3C CH HACK Y CH3 H₃C. 1) Addition of HCl across the C=C gives Markovnikov's product. Upon reaction with NaOEt it give substitution via SN2. However, there is always a possiblity that elimination as well may happen but to know that more information on reaction conditions is needed. Hz A CH. 1) BH3; THE CH3 2) H2O2, NaOEt H2CH3 HO H₃C a CH₂ 2) Hydroboration gives less substituted alcohol and 4) 03, hence heating with H2SO4 gives dehydration product the diene and upon ozonolysis it give respective aldehydes via reduction workup. HO HO 3) H2S04. 15) DMS Hzc OA0002 oxaldehyde

CH3 СН3 Br CHg 1) NaoEt orman parte 2) HBr CH, И har сня - No further reaction with Br2, H20 and H2SO4. "Br H3C CH3 H3 CH3 H3C CH3 NaOEt give 1,2-elimination via E2 mechanism to give alkene product. Addition of HBr gives Markovnikov's product. And then the tert. alkyl bromide will not react with Br2, H20. CH3CH2 CH3 CH2 K OH 1) H2804 CH2) Br2 B CH 4) Dehydration and further 1,2-methyl rearrangment gives alkene and addition of Br2 gives anti addition product. CH3 HS CH2 1) mCPBA 2) H3S+ OH Enantiomer Enantiomer 5) Epoxidation is done with mCPBA and this epoxide is opened with H2S in presence of acid to give anti-product