Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 15, Problem 55P

When compound C, which is often used to model a more frequently occurring unit in lignins, was ozonized, product D was obtained. In a variety of ways it has been established that the stereochemistry of the three-carbon side chain of such lignin units remains largely if not completely unchanged during oxidations like this.

Chapter 15, Problem 55P, When compound C, which is often used to model a more frequently occurring unit in lignins, was

For GC/MS, D was converted to its tetrakis(O-trimethylsilyl) derivative, which had M + 424 m/z. The IR spectrum of D had bands at 3000 c m 1 (broad, strong) and 1710 c m 1 (strong). Its 1 H NMR spectrum had peaks at δ 3.7 (multiplet, 3H) and δ 4.2 (doublet, 1H) after treatment with D 2 O . Its D E P T   13 C NMR spectra had peaks at δ 64 ( C H 2 ) , δ 75 (CH), δ   82 (CH), and δd 177 (C). What is the structure of D, including its stereochemistry?

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Chapter 15 Solutions

Organic Chemistry

Ch. 15 - PRACTICE PROBLEM 15.8 Write resonance structures...Ch. 15 - PRACTICE PROBLEM 15.9 Provide a mechanism for the...Ch. 15 - PRACTICE PROBLEM 15.13 Write mechanisms for the...Ch. 15 - Prob. 14PPCh. 15 - PRACTICE PROBLEM 15.15 Suppose you needed to...Ch. 15 - PRACTICE PROBLEM 15.16 Predict the major product...Ch. 15 - PRACTICE PROBLEM Account for the following...Ch. 15 - PRACTICE PROBLEM 1-Chloro-3-methyl-2-butene...Ch. 15 - Prob. 19PPCh. 15 - PRACTICE PROBLEM 15.20 The following chlorides (Ph...Ch. 15 - Prob. 21PPCh. 15 - Provide a detailed mechanism for each of the...Ch. 15 - 15.34 Provide a detailed mechanism for the...Ch. 15 - Prob. 24PCh. 15 - Many polycyclic aromatic compounds have been...Ch. 15 - Prob. 26PCh. 15 - Prob. 27PCh. 15 - Predict the major product (or products) formed...Ch. 15 - Prob. 29PCh. 15 - Prob. 30PCh. 15 - Predict the major products of the following...Ch. 15 - Prob. 32PCh. 15 - Prob. 33PCh. 15 - Prob. 34PCh. 15 - Starting with aniline, outline a synthesis of each...Ch. 15 - Prob. 36PCh. 15 - 15.37 Propose structures for compounds G–I: Ch. 15 - 2,6-Dichlorophenol has been isolated from the...Ch. 15 - 2-Methylnaphthalene can be synthesized from...Ch. 15 - Show how you might synthesize each of the...Ch. 15 - Prob. 41PCh. 15 - Prob. 42PCh. 15 - 15.47 Provide structures for compounds A and B: Ch. 15 - Prob. 44PCh. 15 - Prob. 45PCh. 15 - Treating cyclohexene with acetyl chloride and...Ch. 15 - 15.47 The tert-butyl group can be used as a...Ch. 15 - When toluene is sulfonated (concentrated H2SO4) at...Ch. 15 - Prob. 49PCh. 15 - 15.50 Heating 1,1,1-triphenylmethanol with ethanol...Ch. 15 - 15.51 (a) Which of the following halides would you...Ch. 15 - Furan undergoes electrophilic aromatic...Ch. 15 - 15.61 Acetanilide was subjected to the following...Ch. 15 - Prob. 54PCh. 15 - When compound C, which is often used to model a...Ch. 15 - The structure of thyroxine, a thyroid hormone that...Ch. 15 - Prob. 2LGPCh. 15 - 3. Deduce the structures of compounds E–L in the...Ch. 15 - Which of the following compounds would be most...Ch. 15 - 15.2 Which of the following is not a...Ch. 15 - Prob. 3QCh. 15 - Complete the following syntheses.
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