With the aid of the mechanism of the reaction sequence, what are the structures of compounds A, B, and C in the series of reactions? C6H5C(CH3)2CH2COOH + PCl3 ----> A(C11H13OCl) A + AlCl3/CS2 ----> B(C11H12O) B + N2H4, OH-, heat, high boiling solvent ----> C(C11H12O)

With the aid of the mechanism of the reaction sequence, what are the structures of compounds A, B, and C in the series of reactions? C6H5C(CH3)2CH2COOH + PCl3 ----> A(C11H13OCl) A + AlCl3/CS2 ----> B(C11H12O) B + N2H4, OH-, heat, high boiling solvent ----> C(C11H12O)

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter11: Reactions Of Alkyl Halides: Nucleophilic Substitutions And Eliminations

Section11.SE: Something Extra

Problem 76AP

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Question

With the aid of the mechanism of the reaction sequence, what are the structures of compounds A, B, and C in the series of reactions?

C₆H₅C(CH₃)₂CH₂COOH + PCl3 ----> A(C₁₁H₁₃OCl)

A + AlCl₃/CS₂ ----> B(C₁₁H₁₂O)

B + N₂H₄, OH^-, heat, high boiling solvent ----> C(C₁₁H₁₂O)

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2) Compound C gave the following proton NMR signals:

a) singlet,1.22 ppm, 6H;

b) Triplet, 1.85 ppm, 2H, J = 7 Hz;

c) triplet, 2.83 ppm, 2H, J = 7 Hz;

d) singlet, 7.02 ppm, 4H.

Sketch the proton NMR spectrum of compound C and assign the chemical shifts to the protons of the compounds.

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