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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鈥檛 split. Thus, proton exchange reaction doesn鈥檛 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

Indicate the number of signals and the multiplicity of each signal in the 1 H NMR spectrum of each of the following compounds:

a)CH3CH2CH2CH2CH2CH3

b)ICH2CH2CH2Br

c)ClCH2CH2CH2Cl

d)ICH2CH2CHBr2

When compound A ( C5H11Br) is treated with HBr, it forms compound B (C5H11Br ). The 1 H NMR spectrum of compound A has a 1H singlet, a 3H doublet, a 6H doublet, and two 1H multiplets. The 1 H NMR spectrum of compound B has a 6H singlet, a 3H triplet, and a 2H quartet. Identify compounds A and B.

Identify the compound with a molecular formula C6H10O that gives the following DEPT 13C NMR spectrum:

How many signals are produced by each of the following compounds in its

a.1HNMRSpectrum?

b. 13CNMR spectrum?

1.

2.

3.

4.

5.

6.

Which underlined proton (or sets of protons) has the greater chemical shift (that is, the higher frequency signal)?
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