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.

Chemistry

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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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Question

Consider all of the following data and answer parts (A) through (C):
When ketone A is treated with an equivalent of CH3MgI 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 AB and A → C.
(C) Write mechanisms for the AC and C D + E reactions.

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