Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
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Textbook Question
Chapter 25.5, Problem 23P
(a) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 26, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer’s disease.
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(a) What product is formed by the Claisen rearrangement of compound Z? (b) Using what you have learned about ring-closing metathesis in Chapter 24, draw the product formed when the product in part (a) is treated with Grubbs catalyst. These two reactions are key steps in the synthesis of garsubellin A, a biologically active natural product that stimulates the synthesis of the neurotransmitter acetylcholine. Compounds of this sort may prove to be useful drugs for the treatment of neurodegenerative diseases such as Alzheimer's disease.
Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
Linalool (the Chapter 9 opening molecule) and lavandulol are two of the major components of lavender oil. (a) What organolithium reagent and carbonyl compound can be used to make each alcohol? (b) How might lavandulol be formed by reduction of a carbonyl compound? (c) Why can’t linalool be prepared by a similar pathway?
Chapter 25 Solutions
Organic Chemistry (6th Edition)
Ch. 25.1 - Prob. 1PCh. 25.2 - Problem 27.2
For each molecular orbital in Figure...Ch. 25.2 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 25.3 - Prob. 4PCh. 25.3 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.3 - Prob. 8PCh. 25.3 - Prob. 9PCh. 25.3 - Problem 27.11
What product would be formed by the...
Ch. 25.4 - Consider cycloheptatrienone and ethylene, and draw...Ch. 25.4 - Problem 27.13
Show that a thermal suprafacial...Ch. 25.4 - Prob. 13PCh. 25.5 - Prob. 17PCh. 25.5 - Prob. 18PCh. 25.5 - Prob. 19PCh. 25.5 - Prob. 20PCh. 25.5 - Prob. 21PCh. 25.5 - Prob. 22PCh. 25.5 - Problem 27.25
(a) What product is formed by the...Ch. 25.6 - Prob. 24PCh. 25 - Prob. 25PCh. 25 - Prob. 26PCh. 25 - Prob. 31PCh. 25 - Prob. 32PCh. 25 - Prob. 33PCh. 25 - Prob. 34PCh. 25 - Prob. 35PCh. 25 - Prob. 36PCh. 25 - Prob. 37PCh. 25 - Prob. 41PCh. 25 - Prob. 42PCh. 25 - Prob. 44PCh. 25 - Prob. 45PCh. 25 - 27.47 What product is formed from the [5,5]...Ch. 25 - 27.52 Draw the products of each reaction.
c....
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