Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter SRP, Problem 26P
Interpretation Introduction
Interpretation:
The structure of the intermediate compound from A to M is to be written and the intermediate formed by the reaction of compound D with N-Bromo succinimide, the stereoisomer of Dianeackerone, are to be represented.
Concept introduction:
Dianeackerone consists of nineteen atoms of carbon, thirty atoms of hydrogen and one tom of oxygen due to which its molecular formula is 
. The IUPAC name of this compound is 
. It is a natural product and has a volatile behavior. It has both 
and 
stereoisomers.
N-Bromo succinimide, also known as NBS, is a type of brominating agent, which is used as a source of bromine in many reactions.
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Compounds A and B are isomers having the molecular formula C4H8O3. Identify A and B on the basis of their 1H NMR spectra.Compound A: δ 1.3 (3H, triplet); 3.6 (2H, quartet); 4.1 (2H, singlet); 11.1 (1H, broad singlet)Compound B: δ 2.6 (2H, triplet); 3.4 (3H, singlet); 3.7 (2H triplet); 11.3 (1H, broad singlet)
Treatment of compound E (molecular formula C4H8O2) with excessCH3CH2MgBr yields compound F (molecular formula C6H14O) afterprotonation with H2O. E shows a strong absorption in its IR spectrum at1743 cm−1. F shows a strong IR absorption at 3600−3200 cm−1. The 1HNMR spectral data of E and F are given. What are the structures of E andF?Compound E signals at 1.2 (triplet, 3 H), 2.0 (singlet, 3 H), and 4.1 (quartet, 2 H) ppm Compound F signals at 0.9 (triplet, 6 H), 1.1 (singlet, 3 H), 1.5 (quartet, 4H), and 1.55 (singlet, 1 H) ppm
Compound C has the molecular formula C5H8O. The IR, 1H, 13C, and DEPT NMR spectra of this compound are shown below.
(a) Calculate the double bond equivalent of compound C and briefly explain what the values obtains represents. Interpret the IR spectrum.
(b) Based on the information provided, determine the structure of compound D.
Chapter SRP Solutions
Organic Chemistry
Ch. SRP - 1. Arrange the compounds of each of the following...Ch. SRP - 2. Arrange the compounds of each of the following...Ch. SRP - Predict the final product from each of the...Ch. SRP - Prob. 4PCh. SRP - Write detailed mechanisms for each of the...Ch. SRP - Prob. 6PCh. SRP - Prob. 7PCh. SRP - Give stereochemical structures for compounds AD:Ch. SRP - Prob. 9PCh. SRP - The remaining steps in the industrial synthesis of...
Ch. SRP - Prob. 11PCh. SRP - Prob. 12PCh. SRP - Prob. 13PCh. SRP - Prob. 14PCh. SRP - 17. Show how you would modify the synthesis given...Ch. SRP - Prob. 16PCh. SRP - Give structures for compounds AD. Compound D gives...Ch. SRP - The tranquilizing drug meprobamate (Equanil or...Ch. SRP - Prob. 19PCh. SRP - 22. Outlined here is the synthesis of a central...Ch. SRP - 23. What are compounds A and B? Compound B has a...Ch. SRP - Prob. 22PCh. SRP - Prob. 26PCh. SRP - 28. Compound Y shows prominent IR absorption...Ch. SRP - Prob. 24PCh. SRP - Consider this reaction involving peracetic acid:...
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