Consider all of the following data and answer parts (A) through (C): When ketone A is treated with an equivalent of CH3Mgl in Et₂0 followed by acid (H30+) workup, two constitutional isomers B and C (C5H100) are isolated. The minor isomer B is a ketone. Isomer C decolorizes solutions of Br₂ and permagnate (i.e. it's an alkene - Chem210). When treated with HCl(aq), C gives two constitutional isomers D and E (C5H9Cl) - Chem210. Chloride D, the major product gives 2-methyl-1,3-butadiene when treated with potassium t-butoxide - Chem210. Compound B also is identical to the product obtained from the oxymercuration of 1-pentyne. (A) Identify compounds A through E by structure. (B) Classify both the A → B and A → C. (C) Write mechanisms for the A ⇒ C and C D + E reactions.

Consider all of the following data and answer parts (A) through (C): When ketone A is treated with an equivalent of CH3Mgl in Et₂0 followed by acid (H30+) workup, two constitutional isomers B and C (C5H100) are isolated. The minor isomer B is a ketone. Isomer C decolorizes solutions of Br₂ and permagnate (i.e. it's an alkene - Chem210). When treated with HCl(aq), C gives two constitutional isomers D and E (C5H9Cl) - Chem210. Chloride D, the major product gives 2-methyl-1,3-butadiene when treated with potassium t-butoxide - Chem210. Compound B also is identical to the product obtained from the oxymercuration of 1-pentyne. (A) Identify compounds A through E by structure. (B) Classify both the A → B and A → C. (C) Write mechanisms for the A ⇒ C and C D + E reactions.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 50MP

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