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Give the structure that corresponds to each of the following molecular formulas and NMR

Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise ISBN: 9781936221349 461

Solution for problem 13.4 Chapter 13

Organic Chemistry | 6th Edition

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Organic Chemistry | 6th Edition | ISBN: 9781936221349 | Authors: Marc Loudon, Jim Parise

Organic Chemistry | 6th Edition

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Problem 13.4

Give the structure that corresponds to each of the following molecular formulas and NMR spectra: (a) C5H12; d 0.93, s (b) C5H10; d 1.5, s (c) C4H10O2: d 1.36 (3H, d, J 5 5.5 Hz); d 3.32 (6H, s); d 4.63 (1H, q, J 5 5. 5 Hz) (d) C7H16O; NMR spectrum in Fig. P13.40a. (e) C8H16: NMR spectrum in Fig. P13.40b. This compound undergoes catalytic hydrogenation to give 2,2,4-trimethylpentane. (f) C7H12Cl2: d 1.07 (9H, s); d 2.28 (2H, d, J 5 6 Hz); d 5.77 (1H, t, J 5 6 Hz). (g) C2H2Br2F2: d 4.02 (t, J 5 16 Hz) (h) C2H2F3I: d 3.56 (q, J 5 10 Hz) (i) C7H16O4: d 1.93 (t, J 5 6 Hz); d 3.35 (s); d 4.49 (t, J 5 6 Hz); relative integral 1 : 6 : 1 (j) C6H14O: d 0.91 (6H, d, J 5 7 Hz); d 1.17 (6H, s); d 1.48 (1H, s; disappears following D2O shake); d 1.65 (1H, septet, J 5 7 Hz) 13C NMR: d 17.6, d 26.5, d 38.7, d 73.2

Step-by-Step Solution:

Problem 13.4

Give the structure that corresponds to each of the following molecular formulas and NMR spectra:

                                                      Step by step solution

Step 1 of 9

a)

The given compound has a molecular formula -   .

And gives a singlet at  in the NMR spectra. The molecule must have all protons chemically equivalent. The only possible structure consistent with the given data is 2,2 - dimethylpropane or neopentane.

                                               

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Step 2 of 9

Chapter 13, Problem 13.4 is Solved
Step 3 of 9

Textbook: Organic Chemistry
Edition: 6
Author: Marc Loudon, Jim Parise
ISBN: 9781936221349

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Give the structure that corresponds to each of the following molecular formulas and NMR