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.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Designing a Synthesis

Organic synthesis is a branch of chemical synthesis that involves the planned construction of organic compounds/molecules from smaller units that possess functional groups. Friedrich Wöhler was the first scientist who designed the synthesis of an organic compound, urea from inorganic starting materials silver cyanate with ammonium chloride via a simple, one-step synthesis.

Question

Exercise:
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.
CH2
Route I
Ketone, A
Alkene, B
1. CH,MgBr, H,O
2 H,SO, heat
Route II
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.

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