Chapter 14: Q24P (page 640)
Explain the relative chemical shifts of the benzene ring protons in Figure 14.18.

Short Answer
For proton a it is 7.52 ppm.
For proton b it is 7.64 ppm.
For proton c it is 8.21 ppm.
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Chapter 14: Q24P (page 640)
Explain the relative chemical shifts of the benzene ring protons in Figure 14.18.

For proton a it is 7.52 ppm.
For proton b it is 7.64 ppm.
For proton c it is 8.21 ppm.
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When compound A ( ) is treated with HBr, it forms compound B ( ). 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.
Which has a greater chemical shift for the proton, the proton H1NMR spectrum of pure ethanol or the proton H1NMR spectrum of ethanol dissolved in CH2Cl2.
Which underlined proton (or sets of protons) has the greater chemical shift (that is, the higher frequency signal)?

Propose a mechanism for proton exchange of an alcohol in aqueous base.
Identify the compound with a molecular formula that gives the following DEPT 13C NMR spectrum:

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