Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 2, Problem 56P
Compound C is asymmetric, has molecular formula
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There are several isomeric alkanes of molecular formula C6H14.Two of these exhibit the following 1H-NMR spectra. Propose a structure for each of the isomers.
Isomer A: δ = 0.84 (d, 12 H), 1.39 (septet, 2H) ppm
Isomer B: δ = 0.84 (t, 3 H), 0.86 (s, 9H), 1.22 (q, 2H) ppm
Compound B of molecular formula C9H19N shows a noteworthy infrared absorption at 3300 cm-1. Its 1H-NMR spectrum shows three singlets – δ 1.0 (6H), 1.1 (12H), 1.4 (1H) ppm. Its 13C-NMR spectrum has four signals – δ 25, 28, 41, 64 ppm. Suggest a structure for this compound.
Please show work.
A hydrocarbon, compound B, has molecular formula C6H6, and gave an NMR spectrum with two signals: delta 6.55 pm and delta 3.84 pm with peak ratio of 2:1. When warmed in pyridine for three hr, compound B quantitatively converts to benzene. Mild hydrogenation of B yielded another compound C with mass spectrum of m/z 82. Infrared spectrum showed no double bonds; NMR spectrum showed one broad peak at delta 2.34 ppm. With this information, address the following questions.
a) How many rings are in compound C?
b) How many rings are probably in B? How many double bonds are in B?
c) Can you suggest a structure for compounds B and C?
d) In the NMR spectrum of B, the up-field signal was a quintet, and the down field signal was a triplet. How must you account for these splitting patterns?
Chapter 2 Solutions
Organic Chemistry
Ch. 2 - Practice Problem 2.1
Propose structures for two...Ch. 2 - Prob. 2PPCh. 2 - Prob. 3PPCh. 2 - Prob. 4PPCh. 2 - Prob. 5PPCh. 2 - Practice Problem 2.6
Using a three-dimensional...Ch. 2 - Practice Problem 2.7
Trichloromethane (, also...Ch. 2 - Prob. 8PPCh. 2 - Prob. 9PPCh. 2 - Practice Problem 2.10
Write bond-line structural...
Ch. 2 - Practice Problem 2.11 Although we shall discuss...Ch. 2 - Practice Problem 2.12 Write bond-line structural...Ch. 2 - Prob. 13PPCh. 2 - Practice Problem 2.14
One way of naming ethers is...Ch. 2 - Practice Problem 2.15 Eugenol is the main...Ch. 2 - Practice Problem 2.16
One way of naming amines is...Ch. 2 - Practice Problem 2.17 Which amines in Practice...Ch. 2 - Prob. 18PPCh. 2 - Prob. 19PPCh. 2 - Practice Problem 2.20
Write bond-line formulas for...Ch. 2 - Practice Problem 2.21
Write bond-line formulas for...Ch. 2 - Practice Problem 2.22
Write bond-line formulas for...Ch. 2 - Prob. 23PPCh. 2 - Practice Problem 2.24 Write another resonance...Ch. 2 - Prob. 25PPCh. 2 - Practice Problem 2.26
Which compound would you...Ch. 2 - Practice Problem 2.27 Arrange the following...Ch. 2 - Prob. 28PPCh. 2 - Prob. 29PCh. 2 - Identify all of the functional groups in each of...Ch. 2 - 2.31 There are four alkyl bromides with the...Ch. 2 - Prob. 32PCh. 2 - Classify the following alcohols as primary,...Ch. 2 - 2.34 Classify the following amines as primary,...Ch. 2 - Prob. 35PCh. 2 - Identify all of the functional groups in Crixivan,...Ch. 2 - 2.37 Identify all of the functional groups in...Ch. 2 - 2.38 (a) Indicate the hydrophobic and hydrophilic...Ch. 2 - Hydrogen fluoride has a dipole moment of 1.83 D;...Ch. 2 - 2.40 Why does one expect the cis isomer of an...Ch. 2 - Prob. 41PCh. 2 - Prob. 42PCh. 2 - Prob. 43PCh. 2 - 2.44 Consider each of the following molecules in...Ch. 2 - True or false: For a molecule to be polar, the...Ch. 2 - 2.46 Which compound in each of the following...Ch. 2 - Prob. 47PCh. 2 - The IR spectrum of propanoic acid (Fig. 2.16)...Ch. 2 - Prob. 49PCh. 2 - Write structural formulas for four compounds with...Ch. 2 - There are four amides with the formula C3H7NO. (a)...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - 2.56 Compound C is asymmetric, has molecular...Ch. 2 - 2.57 Examine the diagram showing an -helical...Ch. 2 - Prob. 1LGPCh. 2 - Prob. 2LGPCh. 2 - Prob. 3LGPCh. 2 - Consider the molecular formula C4H8O2. Predict...Ch. 2 - Consider the molecular formula C4H8O2. If any of...Ch. 2 - Prob. 6LGPCh. 2 - Consider the molecular formula.
7. Pick five...Ch. 2 - Prob. 8LGP
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