Chapter 13: Q19P (page 677)
Propose mechanisms to show the interchange of protons between ethanol molecules under
- Acid catalysis
- Base catalysis.
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Chapter 13: Q19P (page 677)
Propose mechanisms to show the interchange of protons between ethanol molecules under
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(A true story.) A major university was designated as a national nuclear magnetic resonance center by the National Science Foundation. Several large superconducting instruments were being installed when a government safety inspector appeared and demanded to know what provisions were being made to handle the nuclear waste produced by these instruments. Assume you are the manager of the NMR center and offer an explanation that could be understood by a nonscientist.
When 2-chloro-2-methylbutane is treated with a variety of strong bases, the products always seem to contain two isomers (A and B) of formula. When sodium hydroxide is used as base, isomer A predominates. When potassium tert-butoxide is used as the base, isomer B predominates. The
and
NMR spectra of A and B are given below.

Question:Using a 60-MHz spectrometer, a chemist observes the following absorption: doublet, J = 7 Hz, at 4.00
(a) What would the chemical shift () be in the 500-MHz spectrum?
(b) What would the splitting value J be in the 500-MHz spectrum?
(c) How many hertz from the TMS peak is this absorption in the 60-MHz spectrum? In the 500-MHz spectrum?
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 at1.1), yet the product alcohol, a racemic mixture, shows two different
doublets, one at
0.75 and one around
1.0.

Question: Give the spectral assignments for the protons in isobutyl alcohol (Solved Problem 13-4). For example, Ha is a singlet, area = 1, at 2.4
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