Organic Chemistry (6th Edition)
6th Edition
ISBN: 9781260119107
Author: Janice Gorzynski Smith
Publisher: McGraw Hill Education
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 25.5, Problem 20P
Interpretation Introduction
Interpretation: The product formed on protonation of the intermediate enolate formed in anionic oxy-Cope rearrangement of given unsaturated alcohol is to be predicted.
Concept introduction: Anionic oxy-Cope rearrangement is a thermal
Sigmatropic rearrangements are pericyclic reactions which takes place by concerted mechanism. In these rearrangements migration of sigma bond takes place.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Answer the following question about curcumin, a yellow pigmentisolated from turmeric, a tropical perennial in the ginger family and aprincipal ingredient in curry powder.
Most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols.
Propose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.
Draw the keto form of the following enol.
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....
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- The key step in a reported laboratory synthesis of sativene, a hydrocarbon isolated from the mold Helminthosporium sativum, involves the following base treatment of a keto tosylate. What kind of reaction is occurring? How would you complete the synthesis?arrow_forwardThe following molecule undergoes an intramolecular reaction in the presence of pyrrolidinium acetate, the protonated form of pyrrolidine. Draw the product of this reaction, assuming that a dehydration reaction takes place.arrow_forwardMinoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction.arrow_forward
- Drawing an Enol and a Ketone Formed by Hydration of an Alkyne Draw the enol intermediate and the ketone product formed in the following reaction.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an a,ẞ-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of 1. formation of an enamine from a ketone. 2. Michael addition to an α,ß-unsaturated carbonyl compound, and 3. hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal. Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. ચર્ચ F Correct HC, CH3 ChemDoodle 2 Draw the structure of the Michael addition product. ChemDoodle Jn (F 106 Correctarrow_forwardDraw the enol form of the following ketonearrow_forward
- Answer the following questions about curcumin, a yellow pigment isolated from turmeric, a tropical perennial in the ginger family and a principal ingredient in curry powder.a.In Chapter 11, we learned that most enols, compounds that contain a hydroxy group bonded to a C=C, are unstable and tautomerize to carbonyl groups. Draw the keto form of the enol of curcumin, and explain why the enol is more stable than many other enols. b.Explain why the enol O—H proton is more acidic than an alcohol O—H proton. c. Why is curcumin colored? d.Explain why curcumin is an antioxidant.arrow_forwardThe compound is treated with the base sodium hydride NaH, an intramolecular SN2 reaction occurs. Please draw both the organic intermediate and the major organic product obtained.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forward
- What is the missing reagent for this reaction? 1) NAOMe olla 2) ? 3) H₂SO4 X مله مثله O ii barrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardDraw the most stable product formed in each of the reactions shown. Reaction (a) 2 NaOEt, EtOH A Draw the product of reaction (a).arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning