ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
12th Edition
ISBN: 9781119664635
Author: Solomons
Publisher: WILEY
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Textbook Question
Chapter 9, Problem 35P
Propose a structure that is consistent with each set of
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)
(k)
(l)
(m)
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Propose a structure consistent with each set of spectral data:
a. C4H8Br2: IR peak at 3000–2850 cm−1; NMR (ppm):
1.87 (singlet, 6 H)
3.86 (singlet, 2 H)
b.C3H6Br2: IR peak at 3000–2850 cm−1; NMR (ppm):
2.4 (quintet) 3.5 (triplet)
c. C5H10O2: IR peak at 1740 cm−1; NMR (ppm):
1.15 (triplet, 3 H) 2.30 (quartet, 2 H)
1.25 (triplet, 3 H) 4.72 (quartet, 2 H)
d.C3H6O: IR peak at 1730 cm−1; NMR (ppm):
1.11 (triplet)
2.46 (multiplet)
9.79 (triplet)
1
anyleh
O,N.
3
H.
9 OH
8.
A
(a) Predict the number of signals in the 'H NMR spectrum. Provide a rough sketch of
the 'H NMR spectrum for Compound A. In your sketch, information such as
coupling patterns and integration of each peak must be shown clearly.
(b) Predict the number of signals in the 13C NMR spectrum. Provide a rough sketch of
the 13C NMR spectrum of compound A.
O:
10. Deduce the identity of the following compound from the 1H NMR data given and briefly
explain.
C7H7NO3: 8 3.9 (3H, singlet), 6.9 (2H, doublet), 8.1 (2H, doublet) (ppm)
Chapter 9 Solutions
ORGANIC CHEMISTRY (LL) W/WILEYPLUS NEXT
Ch. 9 - Prob. 1PPCh. 9 - PRACTICE PROBLEM 9.2 What compound with molecular...Ch. 9 - PRACTICE PROBLEM 9.3
Using the method of Section...Ch. 9 - PRACTICE PROBLEM 9.4 How many signals would each...Ch. 9 - Prob. 5PPCh. 9 - Prob. 6PPCh. 9 - PRACTICE PROBLEM 9.7
The relative chemical shifts...Ch. 9 - Prob. 8PPCh. 9 - PRACTICE PROBLEM 9.9 Propose a structure for...Ch. 9 - PRACTICE PROBLEM 9.10
What is the dihedral angle...
Ch. 9 - PRACTICE PROBLEM 9.11 Draw the most stable chair...Ch. 9 - Prob. 12PPCh. 9 - PRACTICE PROBLEM 9.13 How many signals would you...Ch. 9 - Prob. 14PPCh. 9 - Prob. 15PPCh. 9 - Prob. 16PPCh. 9 - Prob. 17PPCh. 9 - PRACTICE PROBLEM 9.18
What are the expected ratios...Ch. 9 - Prob. 19PPCh. 9 - How many 1H NMR signals (not peaks) would you...Ch. 9 - How many 13C NMR signals would you predict for...Ch. 9 - Prob. 22PCh. 9 - Prob. 23PCh. 9 - Prob. 24PCh. 9 - Compound Q has the molecular formula C7H8. The...Ch. 9 - 9.26 Explain in detail how you would distinguish...Ch. 9 - Compound S (C8H16) reacts with one mole of bromine...Ch. 9 - A compound with molecular formula C4H8O has a...Ch. 9 - In the mass spectrum of 2, 6-dimethyl-4-heptanol...Ch. 9 - Prob. 30PCh. 9 - What are the masses and structures of the ions...Ch. 9 - Prob. 32PCh. 9 - Ethyl bromide and methoxybenzene (shown below)...Ch. 9 - 9.34 The homologous series of primary amines, ,...Ch. 9 - Propose a structure that is consistent with each...Ch. 9 - 9.36 Propose structures for compounds E and F....Ch. 9 - 9.37 Use the NMR and IR data below to propose a...Ch. 9 - 9.38 When dissolved in , a compound (K) with the...Ch. 9 - Compound T (C5H8O) has a strong IR absorption band...Ch. 9 - Prob. 40PCh. 9 - Deduce the structure of the compound that gives...Ch. 9 - Deduce the structure of the compound that gives...Ch. 9 - The 1H NMR spectrum of a solution of 1,...Ch. 9 - Acetic acid has a mass spectrum showing a...Ch. 9 - The 1H NMR peak for the hydroxyl proton of...Ch. 9 - The 1H NMR study of DMF (N, N-dimethylformamide)...Ch. 9 - 9.48 The mass spectra of many benzene derivatives...Ch. 9 - Prob. 49PCh. 9 - 1. Given the following information, elucidate the...Ch. 9 - Two compounds with the molecular formula C5H10O...
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