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.
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.
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Part 3: AHm,system
Mass of 1.00 M HCI
Vol. of 1.00 M HCI
Mass of NaOH(s)
Total Mass in Calorimeter
Mole product if
HCI limiting reactant
Trial 1
62.4009
1.511g
Mole product if
NaOH limiting reactant
Limiting reactant
Initial Temperature
Final Temperature
23.8°C
37.6°C
Change in Temperature
AHm,system (calculated)
Average AHm,system
(calculated)
(calculated)
(calculated)
Trial 2
64.006g
1.9599
(calculated)
(calculated)
(calculated)
(calculated)
(calculated)
(calculated)
24.7°C
41.9°C
(calculated)
(calculated)
(2 pts. each)
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Chapter 12 Solutions
Organic Chemistry
Ch. 12 - Prob. 1PPCh. 12 - Prob. 2PPCh. 12 - Prob. 3PPCh. 12 - PRACTICE PROBLEM 12.4 Predict the products of the...Ch. 12 - Prob. 5PPCh. 12 - Prob. 6PPCh. 12 - Practice Problem 12.7
Provide retrosynthetic...Ch. 12 - Prob. 8PPCh. 12 - What products would you expect from the reaction...Ch. 12 - What products would you expect from the reaction...
Ch. 12 - What product (or products) would be formed from...Ch. 12 - Prob. 12PCh. 12 - 12.13 Write reaction conditions and the product...Ch. 12 - Prob. 14PCh. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the organic product from each of the...Ch. 12 - Predict the major organic product from each of the...Ch. 12 - Synthesize each of the following compounds from...Ch. 12 - Prob. 20PCh. 12 - 21. Write a mechanism for the following reaction....Ch. 12 - Prob. 22PCh. 12 - 23. What organic products A-H would you expect...Ch. 12 - Prob. 24PCh. 12 - Show how 1-pentanol could be transformed into each...Ch. 12 - Provide the reagents needed to accomplish...Ch. 12 - Prob. 27PCh. 12 - For each of the following alcohols, write a...Ch. 12 - Prob. 29PCh. 12 - Prob. 30PCh. 12 - Prob. 31PCh. 12 - Prob. 32PCh. 12 - Predict the major organic product from each of the...Ch. 12 - 34. Synthesize the following compound using...Ch. 12 - Prob. 35PCh. 12 - Prob. 36PCh. 12 - 37. Explain how and IR spectroscopy could be used...Ch. 12 - 38. An unknown X shows a broad absorption band in...Ch. 12 - Prob. 39PCh. 12 - The problem below is directed toward devising a...
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