Ketone A can be converted to alkene B in a one-step reaction via route I. It can also be converted to alkenes B and C via nucleophilic addition with a Grignard reagent followed by dehydration reaction with sulfuric acid in route II. CH, Route Ketone, A Alkene, B 1. CH,MgBr, H,O 2 H,S0, heat Route I| Alkenes, B and C a) Provide a suitable reagent for the conversion of ketone A to alkene B in route I above. b) Suggest the structure of the intermediate in route Il and write a mechanism for the reaction of ketone A with the Grignard reaction. c) Draw the structure of alkene C and identify which alkene is the major product in route II. d) If you were assigned to synthesize alkene B from ketone A, which route would you use for the synthesis? Provide reasons for your choice of synthesis.

Ketone A can be converted to alkene B in a one-step reaction via route I. It can also be converted to alkenes B and C via nucleophilic addition with a Grignard reagent followed by dehydration reaction with sulfuric acid in route II. CH, Route Ketone, A Alkene, B 1. CH,MgBr, H,O 2 H,S0, heat Route I| Alkenes, B and C a) Provide a suitable reagent for the conversion of ketone A to alkene B in route I above. b) Suggest the structure of the intermediate in route Il and write a mechanism for the reaction of ketone A with the Grignard reaction. c) Draw the structure of alkene C and identify which alkene is the major product in route II. d) If you were assigned to synthesize alkene B from ketone A, which route would you use for the synthesis? Provide reasons for your choice of synthesis.

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter25: Enolate & Enol Nucleophiles

Section: Chapter Questions

Problem 10CTQ

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