Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 12, Problem LGP

The problem below is directed toward devising a hypothetical pathway for the synthesis of the acyclic central portion of Crixivan (Merck and Company’s HIV protease inhibitor). Note that your synthesis might not adequately control the stereochemistry during each step, but for this particular exercise chat is not expected.

Chapter 12, Problem LGP, The problem below is directed toward devising a hypothetical pathway for the synthesis of the , example  1

Fill in missing compounds and reagents in the following outline of a hypothetical synthesis of the acyclic central portion of Crixivan. Note that more than one intermediate compound may be involved between some of the structures shown below.

Chapter 12, Problem LGP, The problem below is directed toward devising a hypothetical pathway for the synthesis of the , example  2

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In the box below, specify which of the given compounds are very soluble in polar aprotic solvents. You may select more than one compound. Choose one or more: NaCl NH4Cl CH3CH2CH2CH2CH2CN CH3CH2OH hexan-2-one NaOH CH3SCH3
On the following structure, select all of the atoms that could ACCEPT a hydrogen bond. Ignore possible complications of aromaticity. When selecting be sure to click on the center of the atom.
Rank the compounds below from lowest to highest melting point.

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