Organic Chemistry, 12e Study Guide/Student Solutions Manual
Organic Chemistry, 12e Study Guide/Student Solutions Manual
12th Edition
ISBN: 9781119077329
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 10, Problem 14PP

Practice Problem 10.14

Show how the following compounds could be synthesized from phenylacetylene ( C 6 H 5 C C H ) :

(a) 1-phenylpropyne,

(b) 1-phenyl-1-butyne,

(c)(Z)-1-phenylpropene, and

(d)(E)-1-phenylpropene.

Begin each synthesis by writing a retrosynthetic analysis.

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Practice Problem 13.36b Problem 13.34 outlines a general method for the preparation of cis- or trans-disubstituted epoxides. Using that method, identify what reagents you would use to prepare the following epoxide from acetylene: H" 'Et The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C D DMP or PCC На, Pt EtBr PHCH2BR E F H H2SO4, H20, HgSO4 МСРВА (RCO3зН) Na, NH3 (/) H2, Lindlar's cat. I K TSCI, py PhBr NANH2 1) EtMgBr; 2) H30+
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Practice Problem 13.37a Draw the major organic product of the following reaction sequence. 1) RCO3H 2) MeMgBr 3) H20

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Organic Chemistry, 12e Study Guide/Student Solutions Manual

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