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Organic Chemistry: A Guided Inquiry

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter24: Carboxylic Acids & Derivatives

Section: Chapter Questions

Problem 3E

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Question

When phenyl-5-bromopentanone is treated with
triphenylphosphine, followed by base, a compound
is produced whose formula is C11H12. Its 13C NMR
spectrum has nine signals, six of which appear between
120 and 140 ppm and three of which appear below
50 ppm. For this reaction, draw the complete, detailed
mechanism, as well as the major organic product.
1. P(C6H5)3
Br
C11H12
2. NaOCH,CH3

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