Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Chapter 17, Problem 17.69P
Although benzene itself absorbs at
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Although benzene itself absorbs at 128 ppm in its 13C NMR spectrum, the carbons of substituted benzenes absorb either upeld or downeld from this value depending on the substituent. Explain the observed values for the carbon ortho to the given substituent in the monosubstituted benzene derivatives X and Y.
An unknown compound has a molecular formula of C,H,O. Its IR spectrum shows prominent absorptions at 2980, 2960, and 1718 cm . It exhibits the
following signals in its H NMR spectrum (ppm): 1.06 (triplet, 3H), 2.12 (singlet, 3H), 2.45 (quartet, 2H); and the following signals in its ¹3C NMR spectrum (
ppm): 7.6, 29.5, 36.8, 208.8.
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Compound A has molecular formula C7H7X. Its 1H-NMR spectrum shows a singlet at 2.26 ppm and two doublets, one at 6.95 ppm and one at 7.28 ppm. The singlet has an integral of three and the doublets each have an integral of two. Its 13C-NMR shows five signals. The mass spectrum of A shows a peak at m/z = 170 and another peak at m/z = 172; the relative height of the two peaks is 1:1 respectively.
- Identify what atom X is, explaining your reasoning
- Identify Compound A, explaining your reasoning
Compound A is treated with a mixture of nitric and sulfuric acids to generate Compound B. The 1H-NMR spectrum of B shows two singlets, one at 2.52 pm and one at 8.13 ppm. The 13C-NMR spectrum of B shows five signals. The mass spectrum of B shows a peak at m/z = 260 and another peak at m/z = 262; the relative height of the two peaks is 1:1 respectively.
- Identify compound B, explaining your reasoning
Compound B is treated with sodium ethoxide to generate compound C. The 1H-NMR spectrum of C shows…
Chapter 17 Solutions
Organic Chemistry
Ch. 17 - Prob. 17.1PCh. 17 - Problem 17.2 What orbitals are used to form the...Ch. 17 - Problem-17.3. Give the IUPAC name for each...Ch. 17 - Prob. 17.4PCh. 17 - Problem-17.5 What is the structure of propofol,...Ch. 17 - Problem 17.6 What is the structure of a compound...Ch. 17 - Problem 17.7 How many NMR signals does each...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10P
Ch. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - Problem 17.14 Januvia, the trade name for...Ch. 17 - Prob. 17.15PCh. 17 - Problem 17.16 Rank the following compounds in...Ch. 17 - Problem 17.17 Draw the seven resonance structures...Ch. 17 - Prob. 17.18PCh. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Problem 17.22 How many NMR signals does ...Ch. 17 - 17.23 Name each compound and state how many lines...Ch. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - Prob. 17.26PCh. 17 - 17.27 Give the IUPAC name for each compounds.
a....Ch. 17 - 17.28 Draw a structure corresponding to each...Ch. 17 - 17.29 a. Draw the 14 constitutional isomers of...Ch. 17 - Prob. 17.30PCh. 17 - Prob. 17.31PCh. 17 - Prob. 17.32PCh. 17 - 17.33 Label each compound as aromatic,...Ch. 17 - Prob. 17.34PCh. 17 - 17.35 Pentalene, azulene, and heptalene are...Ch. 17 - 17.36 The purine heterocycle occurs commonly in...Ch. 17 - Prob. 17.37PCh. 17 - 17.38
How many electrons does C contain?
How...Ch. 17 - Prob. 17.39PCh. 17 - 17.40 Explain the observed rate of reactivity of...Ch. 17 - 17.41 Draw a stepwise mechanism for the following...Ch. 17 - Prob. 17.42PCh. 17 - 17.43 Draw additional resonance structures for...Ch. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - 17.46 Which compound in each pair is the stronger...Ch. 17 - 17.47 Treatment of indene with forms its...Ch. 17 - Prob. 17.48PCh. 17 - 17.49 Draw the conjugate bases of pyrrole and...Ch. 17 - 17.50 a. Explain why protonation of pyrrole occurs...Ch. 17 - Prob. 17.51PCh. 17 - Prob. 17.52PCh. 17 - 17.53 How many signals does each compound...Ch. 17 - 17.54 Which of the diethylbenzene isomers (ortho,...Ch. 17 - 17.55 Propose a structure consistent with each...Ch. 17 - 17.56 Propose a structure consistent with each...Ch. 17 - 17.57 Thymol (molecular formula ) is the major...Ch. 17 - 17.58 You have a sample of a compound of molecular...Ch. 17 - 17.59 Explain why tetrahydrofuran has a higher...Ch. 17 - 17.60 Rizatriptan (trade name Maxalt) is a...Ch. 17 - 17.61 Zolpidem (trade name Ambien) promotes the...Ch. 17 - 17.62 Answer the following questions about...Ch. 17 - 17.63 Stanozolol is an anabolic steroid that...Ch. 17 - Prob. 17.64PCh. 17 - 17.65 Use the observed data to decide whether C...Ch. 17 - Prob. 17.66PCh. 17 - Prob. 17.67PCh. 17 - Prob. 17.68PCh. 17 - 17.69 Although benzene itself absorbs at in its ...
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