Organic Chemistry
5th Edition
ISBN: 9780078021558
Author: Janice Gorzynski Smith Dr.
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 14, Problem 14.25P
Propose a structure for a compound of molecular formula
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Part VII. Below are the 'HNMR, 13 C-NMR, COSY 2D- NMR, and HSQC 2D-NMR (similar with HETCOR but axes are reversed) spectra of an
organic compound with molecular formula C6H1003 - Assign chemical shift values to the H and c atoms of the
compound. Find the structure. Show complete solutions.
Predicted 1H NMR Spectrum
4.7 4.6 4.5 4.4 4.3 4.2 4.1 4.0 3.9 3.8 3.7 3.6 3.5 3.4 3.3 3.2 3.1 3.0 2.9 2.8 2.7 2.6 2.5 2.4 2.3 2.2 2.1 2.0 1.9 1.8 1.7 1.6 1.5 1.4 1.3 1.2 1.1
f1 (ppm)
Predicted 13C NMR Spectrum
100
f1 (ppm)
30
220 210 200 190 180
170
160 150 140 130 120
110
90
80
70
-26
60
50
40
46
30
20
115
10
1.0 0.9 0.8
0
-10
Q: Arrange BCC and Fec
metals, in sequence from the
Fable (Dr. R's slides) and
Calculate Volume and Density.
Aa
BCC
V
52 5
SFCC
None
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - Problem 14.1 The NMR spectrum of recorded on a ...Ch. 14 - Prob. 14.2PCh. 14 - How many NMR signals does each compound show?
a....Ch. 14 - How many 1H NMR signals does each...Ch. 14 - How many 1H NMR signals does each compound give?...Ch. 14 - Label the protons in each highlighted CH2 group as...Ch. 14 - How many 1H NMR signals would you expect for each...Ch. 14 - Prob. 14.8PCh. 14 - For each compound, first label each different type...Ch. 14 - Label each statement as True or False. a. When a...
Ch. 14 - Prob. 14.11PCh. 14 - Problem 14.12 Which compound give a NMR spectrum...Ch. 14 - Prob. 14.13PCh. 14 - Prob. 14.14PCh. 14 - For each compound give the number of 1H NMR...Ch. 14 - Prob. 14.16PCh. 14 - Prob. 14.17PCh. 14 - Problem 14.18 Describe the NMR spectrum of each...Ch. 14 - Problem 14.19 Draw a splitting diagram for in ,...Ch. 14 - Problem 14.20 Identify A and B, isomers of...Ch. 14 - Problem 14.21 How many signals are present in the ...Ch. 14 - Problem 14.22 What protons in alcohol A give rise...Ch. 14 - How many peaks are observed in the NMR signal for...Ch. 14 -
Problem 14.24 Propose a structure for a compound...Ch. 14 - Problem 14.25 Propose a structure for a compound...Ch. 14 - Problem 14.26. Identify products A and B from the...Ch. 14 - Problem 14.27 How many lines are observed in the ...Ch. 14 - Problem 14.28 Draw all constitutional isomers of...Ch. 14 - Problem 14.29 Esters of chrysanthemic acid are...Ch. 14 - Prob. 14.30PCh. 14 - Problem 14.31 Identify the carbon atoms that give...Ch. 14 - Problem 14.32 A compound of molecular formula ...Ch. 14 - Problem 14.33 Draw the structure of a compound of...Ch. 14 - 14.34 (a) How many NMR signals does each of the...Ch. 14 - 14.35 (a) How many NMR signals does each compound...Ch. 14 - Prob. 14.36PCh. 14 - 14.37 How many NMR signals does each natural...Ch. 14 - Prob. 14.38PCh. 14 - 14.39 What effect does increasing the operating...Ch. 14 - Prob. 14.40PCh. 14 - 14.41 How could you use chemical shift and...Ch. 14 - Prob. 14.42PCh. 14 - 14.43 How can you use NMR spectroscopy to...Ch. 14 - Prob. 14.44PCh. 14 - Prob. 14.45PCh. 14 - Prob. 14.46PCh. 14 - Prob. 14.47PCh. 14 - 14.48 How many NMR signals does each compound...Ch. 14 - 14.49 Rank the highlighted carbon atoms in each...Ch. 14 - 14.50 Identify the carbon atoms that give rise to...Ch. 14 - 14.51 a. How many signals does dimethyl...Ch. 14 - 14.52 Answer the following questions about each of...Ch. 14 - 14.53 Propose a structure consistent with each set...Ch. 14 - 14.54 Identify the structures of isomers A and B...Ch. 14 - 14.55 Reaction of with affords compound W,...Ch. 14 - 14.56 Treatment of with , followed by aqueous
...Ch. 14 - 14.57 Compound C has a molecular ion in its mass...Ch. 14 - 14.58 As we will learn in Chapter 20, reaction of ...Ch. 14 - 14.59 Identify the structures of isomers E and F...Ch. 14 - 14.59 Identify the structures of isomers H and I...Ch. 14 - 14.61 Propose a structure consistent with each set...Ch. 14 - 14.62 Reaction of with , followed by treatment...Ch. 14 - Reaction of aldehyde D with amino alcohol E in the...Ch. 14 - 14.64 Propose a structure consistent with each set...Ch. 14 - 14.65 In the presence of a small amount of acid, a...Ch. 14 - 14.66 Treatment of with affords two products (M...Ch. 14 - 14.67 Compound O has molecular formula and shows...Ch. 14 - 14.68 Compound P has molecular formula . Deduce...Ch. 14 - 14.69 Treatment of with strong base followed by ...Ch. 14 - 14.70 When -bromo--dimethylbutane is treated with...Ch. 14 - 14.71 Propose a structure consistent with each set...Ch. 14 - 14.72 Reaction of unknown A with forms...Ch. 14 - Prob. 14.73PCh. 14 - 14.74 -Annulene shows two signals in its ...Ch. 14 - 14.75 Explain why the spectrum of-methylbutan--ol...Ch. 14 - 14.76 Because has an odd mass number, nuclei...Ch. 14 - 14.77 Cyclohex--enone has two protons on its...
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