Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 14, Problem 14.55SP
In 2012, a group led by Professor Masayuki Satake of the University of Tokyo reported the isolation and structure determination of a toxin from a marine algal bloom that decimated the fish population off the New Zealand coast in 1998. Extensive mass spectrometry and NMR experiments ultimately led to the structure shown below, named Brevisulcenal-F. (See Journal of the American Chemical Society, 2012, 134, 4963-4968.) This structure holds the record for the largest number of fused rings, at 17.
- a. How many other groups are present?
- b. How many alcohol groups are present? Classify the alcohols as 1° or 2° or 3°.
- c. Are there any other oxygen-containing functional groups? Which, if any?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
From the following 1H-NMR and 13C-NMR spectra, assign a structure for a compound with a formula of C4H9Br. Give reasons (explanations) for the choosen structure.
Briefly explain or give an introduction to this.
Do an introduction (in a paragraph)
Structure Elucidation of Compounds using Several Spectroscopic Techniques.
1H and 13C NMR Spectroscopy
IR Spectroscopy
Mass Spectroscopy
Cumene
->
i. Butyl chloride
ii. Dimethyl amine
iii. H2, Pt
Provide the bond-line structures for the major organic products obtained in each step
Chapter 14 Solutions
Organic Chemistry (9th Edition)
Ch. 14.2C - Rank the given solvents in decreasing order of...Ch. 14.2D - Prob. 14.2PCh. 14.2D - In the presence of 18-crown-6, potassium...Ch. 14.3B - Give a common name (when possible) and a...Ch. 14.3C - Prob. 14.5PCh. 14.3C - Name the following heterocyclic ethers.Ch. 14.4 - Propose a fragmentation to account for each...Ch. 14.5 - Prob. 14.8PCh. 14.5 - Prob. 14.9PCh. 14.6 - Prob. 14.10P
Ch. 14.7 - Explain why bimolecular condensation is a poor...Ch. 14.7 - Prob. 14.12PCh. 14.7 - Prob. 14.13PCh. 14.8 - Prob. 14.14PCh. 14.8 - Prob. 14.15PCh. 14.8 - Prob. 14.16PCh. 14.10A - Prob. 14.17PCh. 14.10A - Prob. 14.18PCh. 14.10B - Prob. 14.19PCh. 14.11B - Show how you would accomplish the following...Ch. 14.11B - Prob. 14.21PCh. 14.12 - Prob. 14.22PCh. 14.12 - Prob. 14.23PCh. 14.12 - Prob. 14.24PCh. 14.13 - Prob. 14.25PCh. 14.13 - Prob. 14.26PCh. 14.14 - Prob. 14.27PCh. 14.15 - Give the expected products of the following...Ch. 14 - Write structural formulas for the following...Ch. 14 - Give common names for the following compounds. a....Ch. 14 - Give IUPAC names for the following compounds. a....Ch. 14 - Glycerol (propane-1,2,3-triol) is a viscous syrup...Ch. 14 - Prob. 14.33SPCh. 14 - Show how you would make the following ethers,...Ch. 14 - (A true story.) An inexperienced graduate student...Ch. 14 - Prob. 14.36SPCh. 14 - a. Show how you would synthesize the pure (R)...Ch. 14 - a. Predict the values of m/z and the structures of...Ch. 14 - The following reaction resembles the...Ch. 14 - Prob. 14.40SPCh. 14 - Prob. 14.41SPCh. 14 - Prob. 14.42SPCh. 14 - Give the structures of the intermediates...Ch. 14 - Prob. 14.44SPCh. 14 - Show how you would synthesize the following ethers...Ch. 14 - Prob. 14.46SPCh. 14 - Prob. 14.47SPCh. 14 - Prob. 14.48SPCh. 14 - An acid-catalyzed reaction was carried out using...Ch. 14 - Propylene oxide is a chiral molecule. Hydrolysis...Ch. 14 - Prob. 14.51SPCh. 14 - Prob. 14.52SPCh. 14 - Prob. 14.53SPCh. 14 - Prob. 14.54SPCh. 14 - In 2012, a group led by Professor Masayuki Satake...
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 proton NMR spectrum of a compound with formula C8H14O2 is shown. TheDEPT experimental results are tabulated. The infrared spectrum showsmedium-sized bands at 3055, 2960, 2875, and 1660 cm-1and strong bands at1725 and 1185 cm-1. Draw the structure of this compound and assign thecarbon peaks.arrow_forwardThe compound acetophenone has a very similar molar mass to that of benzoic acid and benzamide. However, acetophenone has a much lower m.p. (20 °C) than both such that, by contrast, it is a liquid at room temperature. By considering intermolecular forces and comparing functional group structure, account for this big difference in physical properties.arrow_forwardUse the 1H NMR and IR spectra given below to identify the structures of two isomers (A and B) having molecular formula C4H8O2.arrow_forward
- The German chemist Wilhelm Kӧrner (1839-1925) observed in 1974 that each of the three isomers of dibromobenzene, A, B, and C, gave a different number of tribromobenzenes upon further bromination, allowing him to assign their respective structures. Try to do the same and assign structures to A, B, and C based on the following results: A gives two tribromobenzenes in comparable amounts B gives three tribromobenzenes, one of them in minor quantities C gives only one tribromobenzenearrow_forwardThe mass, IR, and 1H-NMR spectra of a compound are shown below. Suggest a possible structure for the compound, explaining how you reach your decision.arrow_forwardBased on this IR spectrum and 1H NMR spectrum and the given chemical formula is C9H10O2, what would be the chemical structure of the compound? Please give a full analysis of the NMR spectra for given compound.arrow_forward
- The compound whose structure is shown here is acetyl acetone. It exists in two forms:the enol form and the keto form The molecule reacts with OH–to form an anion, [CH3COCHCOCH3] (often abbreviatedacac–for acetylacetonate ion). One or the most interesting aspects of this anion is thatone or more of them can react with transition metal cations to give stable, highlycolored compounds (a) Are the keto and enol forms of acetylacetone resonance forms? Explain youranswer.(b) What is the hybridization or each atom (except H) in the enol form? What changesin hybridization occur when it is transformed into the keto form?(c) What are the electron-pair geometry and molecular geometry around each C atomin the keto and enol forms? What changes in geometry occur when the keto formchanges to the enol form?(d) Draw three possible resonance structures for the acac–ion.(e) Is cis-trans isomerism possible in either the enol or the keto form of acetylacetone?(f) Is the enol form of acetylacetone polar?…arrow_forwardCompound A(C10H12O)gives off oxygen on treatment with sodium metal and also decolorizes Br2 in CCl4 to give organic compound B. Compound A on treatment with I2 in NaOH gives iodoform and salt C which after acidification gives a white solid D(C7H6O2). Using knowledge of organic chemistry identify structures A,B,C and Darrow_forwardPropose structure(s) for the compound and give the physical properties, chemical properties, and hazards for the compounds you propose (do not use Wikipedia). Describe in detail how you arrived at this structure (functional groups from IR spectra, degree of unsaturation, etc.).arrow_forward
- The unknown compound with molecular formula C4H8O3, has infrared absorptions at 1710 and 2500 to 3100 cm^-1 and has ¹H NMR spectrum shown. Analyze the given data and propose a structure for this compound. Explain how you come up with your proposed compound.arrow_forwardCompound A (C5H8) readily reacts with bromine (Br2) at room temperature to discharge the purple colour of bromine and form Compound B (C5H8Br2). When Compound A is treated with H2 in the presence of a transition metal catalyst, it is converted to compound C (C5H10). When treated with HCl, compound A is converted to compound D (C5H9Cl). B, Cand D are saturated compounds. Given this information, propose structural formulas for compounds A, B, C, and D.arrow_forward. Discuss the truth of the following statement. Explain why it is true or false Every SN1 reaction produces racemic mixtures in the productsarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- EBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License