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Chapter 14: Q39P (page 654)

Propose a mechanism for proton exchange of an alcohol in aqueous base.

Short Answer

Expert verified

Mechanism for proton exchange of an alcohol in aqueous base is shown below.

Step by step solution

01

Step-by-Step SolutionStep 1: Proton exchange

When alcohol reacts with a base, proton exchange is faster. These results in spectrum appear to be only one singlet peak for proton. Due to fast proton exchange reaction, adjacent protons don’t split. Thus, proton exchange reaction doesn’t cause splitting.

02

Explanation of the mechanism

Mechanism

When alcohol and base react together, protons bonded to oxygen undergo proton exchange with base. In the mechanism, NaOH base deprotonates methanol and gives alkoxide ion. Methanol undergoes bond cleavage in O-H bond and then proton gets transferred to the base, which results in methoxide and water as products.

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Most popular questions from this chapter

Answer the following questions:

a. What is the relationship between chemical shift in ppm and operating frequency?

b. What is the relationship between chemical shift in hertz and operating frequency?

c. What is the relationship between coupling constant in hertz and operating frequency?

d. How does the operating frequency in NMR spectroscopy compare with the operating frequency in IR and UV/Vis spectroscopy?

Identify each of the following compounds from the 1H NMR data and molecular formula:

a.C4H8Br2: a 6H singlet at 1.97 ppm

a 2H singlet at 3.89 ppm

b. C8H9Br: a 3H doublet at 2.01 ppm

a 1H quartet at 5.14 ppm

a 5H broad singlet at 7.35 ppm

c. C5H10O2: a 3H triplet at 1.15 ppm

a 3H triplet at 1.25 ppm

a 2H quartet at 2.33 ppm

a 2H quartet at 4.13 ppm

The 1H NMR spectra of three isomers with molecular formula C4H9Br are shown here. Which isomer produces which spectrum?

a)

b)

c)

Would it be better to use 1H NMR or 13C NMR spectroscopy to distinguish 1-butene, cis-2-butene, and 2-methylpropene? Explain your answer.

Identify each compound from its molecular formula and itsNMR spectrum:

a) C9H12

b) C5H10O

c)C9H10O2
See all solutions

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