9th Edition

ISBN: 9780136781776

Author: Wade

Publisher: PEARSON CO

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Textbook Question

Chapter 13, Problem 13.55SP

Phenyl Grignard reagent adds to 2-methylpropanal to give the secondary alcohol shown. The proton NMR of 2-methylpropanal shows the two methyl groups as equivalent (one doublet at δ 1.1), yet the product alcohol, a racemic mixture, shows two different 3H doublets, one at δ 0.75 and one around δ 1.0.

Chapter 13, Problem 13.55SP, Phenyl Grignard reagent adds to 2-methylpropanal to give the secondary alcohol shown. The proton NMR

a. Draw a Newman projection of the product along the C1-C2 axis.
b. Explain why the two methyl groups have different NMR chemical shifts. What is the term applied to protons such as these?

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Chapter 13, Problem 13.54SP

Chapter 13, Problem 13.56SP

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Chapter 13 Solutions

EP ORGANIC CHEMISTRY -MOD.MASTERING 18W

Ch. 13.5A - In a 300-MHz spectrometer, the protons in...Ch. 13.5B - Prob. 13.2P Ch. 13.6 - Determine the number of different kinds of protons...Ch. 13.6 - Prob. 13.4P Ch. 13.7 - Draw the integral trace expected for the NMR...Ch. 13.7 - Prob. 13.6P Ch. 13.8C - Draw the NMR spectra you would expect for the...Ch. 13.8D - Draw the NMR spectra you expect for the following...Ch. 13.8D - a. Assign protons to the peaks in the NMR spectrum...Ch. 13.8D - Prob. 13.10P

Ch. 13.8D - Two spectra are shown. Propose a structure that...Ch. 13.9 - Prob. 13.12P Ch. 13.9 - The spectrum of trans-hex-2-enoic acid follows. a....Ch. 13.9 - Prob. 13.14P Ch. 13.9 - Prob. 13.15P Ch. 13.10 - Prob. 13.16P Ch. 13.10 - If the imaginary replacement of either of two...Ch. 13.10 - Predict the theoretical number of different NMR...Ch. 13.11B - Prob. 13.19P Ch. 13.11B - Prob. 13.20P Ch. 13.11B - Prob. 13.21P Ch. 13.11B - Prob. 13.22P Ch. 13.11B - Prob. 13.23P Ch. 13.11B - Prob. 13.24P Ch. 13.12E - Draw the expected broadband-decoupled 13 C N M R...Ch. 13.12E - a. Show which carbon atoms correspond with which...Ch. 13.12E - Repeat Problem13-25, sketching the...Ch. 13.12F - Prob. 13.28P Ch. 13.13 - A bottle of allyl bromide was found to contain a...Ch. 13.13 - A laboratory student was converting cyclohexanol...Ch. 13.14 - Sets of spectra are given for two compounds. For...Ch. 13 - An unknown compound has the molecular formula C 9...Ch. 13 - Prob. 13.34SP Ch. 13 - Predict the approximate chemical shifts of the...Ch. 13 - Prob. 13.36SP Ch. 13 - Prob. 13.37SP Ch. 13 - Prob. 13.38SP Ch. 13 - Prob. 13.39SP Ch. 13 - Prob. 13.40SP Ch. 13 - For each compound shown below. 1. sketch the 13 C...Ch. 13 - Prob. 13.42SP Ch. 13 - Prob. 13.43SP Ch. 13 - Prob. 13.44SP Ch. 13 - Prob. 13.45SP Ch. 13 - Prob. 13.46SP Ch. 13 - A compound was isolated as a minor constituent in...Ch. 13 - Prob. 13.48SP Ch. 13 - The three isomers of dimethylbenzene are commonly...Ch. 13 - a. Draw all six isomers of formula C 4 H 8...Ch. 13 - Prob. 13.51SP Ch. 13 - Hexamethylbenzene undergoes free-radical...Ch. 13 - Each of these four structures has molecular...Ch. 13 - Prob. 13.54SP Ch. 13 - Phenyl Grignard reagent adds to 2-methylpropanal...Ch. 13 - Prob. 13.56SP

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Solution Summary: The author explains the Newman projection of the given product along the C1-C2 axis, which represents the spatial arrangement of bonds on two adjacent atoms in a molecule.

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Chapter 13 Solutions