ORGANIC CHEMISTRY W/BIO...-STUD.SOLN.
5th Edition
ISBN: 9781259920066
Author: SMITH
Publisher: MCG
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 23, Problem 23.19P
Identify A, B, and C, intermediates in the synthesis of the five-membered ring called anΑ-methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Identify A, B, and C, intermediates in the synthesis of the ve-membered ring called an α-methylene-γ-butyrolactone. This heterocyclic ring system is present in some antitumor agents.
The sex pheromone of the common house fly has the molecular formula C23H46. It can be synthesized in the lab using the following synthetic sequence. Give the structures of the pheromone and the intermediates A and B.
n-C13H27C≡CH + n-butyl lithium → A (C15H27Li)
A + n-C8H17Br → B (C23H44)
B + H2 with Lindlar catalyst → the pheromone
A reaction flask contains 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and result in the formation of two olefnic products. What is responsible for the formation of major and minor products. A. Different activated complex involved in the mechanism. B. Bimolecular nucleophilic substitution reaction. C. Bimolecular elimination reaction D. The presence of sodium ethoxide. E. The hybridization nature of secondary carbocation
Chapter 23 Solutions
ORGANIC CHEMISTRY W/BIO...-STUD.SOLN.
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Prob. 23.2PCh. 23 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 23 - Prob. 23.4PCh. 23 - Problem 23.5 Which bonds in the following...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - Prob. 23.8PCh. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.13PCh. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Problem 23.20 Which of the following compounds...Ch. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.22PCh. 23 - Prob. 23.23PCh. 23 - Prob. 23.24PCh. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - 23.31 Draw enol tautomer(s) for each compound.
...Ch. 23 - Prob. 23.32PCh. 23 - Prob. 23.33PCh. 23 - Prob. 23.34PCh. 23 - 23.35 Rank the labeled protons in each compound in...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - Prob. 23.40PCh. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - 23.42 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.43PCh. 23 - Prob. 23.44PCh. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - 23.46 Synthesize each compound from diethyl...Ch. 23 - Prob. 23.47PCh. 23 - Prob. 23.48PCh. 23 - Prob. 23.49PCh. 23 - 23.50 Draw the organic products formed in each...Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.52PCh. 23 - Prob. 23.53PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Prob. 23.56PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.59PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.61PCh. 23 - Prob. 23.62PCh. 23 - 23.63 Synthesize each compound from cyclohexanone...Ch. 23 - Prob. 23.64PCh. 23 - Prob. 23.65PCh. 23 - 23.66 Synthesize (Z)-hept-5-en-2-one from ethyl...Ch. 23 - Prob. 23.67PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - Prob. 23.72PCh. 23 - Prob. 23.73PCh. 23 - Prob. 23.74P
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
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardCyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.arrow_forward-Hydroxyketones and -hydroxyaldehydes are also oxidized by treatment with periodic acid. It is not the -hydroxyketone or aldehyde, however, that undergoes reaction with periodic acid, but the hydrate formed by addition of water to the carbonyl group of the -hydroxyketone or aldehyde. Write a mechanism for the oxidation of this -hydroxyaldehyde by HIO4.arrow_forward
- Terpin, prepared commercially by the acid-catalyzed hydration of limonene, is used medicinally as an expectorant for coughs. (a) Propose a structural formula for terpin and a mechanism for its formation. (b) How many cis, trans isomers are possible for the structural formula you propose?arrow_forwardTreatment of 1-aminoadamantane, C10H17N, with methyl 2,4-dibromobutanoate in the presence of a nonnucleophilic base, R3N, involves two successive SN2 reactions and gives compound A. Propose a structural formula for compound A.arrow_forwardWhen the compound shown below undergoes acid-catalyzed dehydration, a ring expansionoccurs to give the fused-ring product. What type of intermediate is formed in this reaction?Explain the ring expansion in terms of the reaction mechanismarrow_forward
- Several sulfonylureas, a class of compounds containing RSO2NHCONHR, are useful drugs as orally active replacements for injected insulin in patients with adult-onset diabetes. These drugs decrease blood glucose concentrations by stimulating b cells of the pancreas to release insulin and by increasing the sensitivity of insulin receptors in peripheral tissues to insulin stimulation. Tolbutamide is synthesized by the reaction of the sodium salt of p-toluenesulfonamide and ethyl N-butylcarbamate . Propose a mechanism for this step.arrow_forwardGive all the monobromination products of 2-methylpropane (or isobutane) in presence of heat or energy. Identify the major product and propose a mechanism leading to the formation of the major product. Provide a reaction in the termination step.arrow_forwardWhen (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forward
- Which of the following set of reagents will make cyclobutamine from bromocyclobutane? a NaN3 / ethanol and LiAlH4 in ether solution b NH3 and NaBH4 in ethanol solution c NaCN and LiAlH4 in ether solution d NH3 and H2 /Pdarrow_forward(a) Draw the structures of the following compounds :(i) 4-Chloropentan-2-one (ii) p-Nitropropiophenone(b) Give tests to distinguish between the following pairs of compounds :(i) Ethanal and Propanal (ii) Phenol and Benzoic acid(iii) Benzaldehyde and Acetophenonearrow_forwardProvide the reagents necessary to convert (R)-2-chlorobutane to (S)-2-methoxybutane.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
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY