Chapter 14: Q9P (page 527)
Question: For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.
a.

b.

c.

Short Answer
a.

b.

c.

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Chapter 14: Q9P (page 527)
Question: For each compound, first label each different type of proton and then rank the protons in order of increasing chemical shift.
a.

b.

c.

a.

b.

c.

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The 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upfield or downfield from the OH proton?
Question: Identify the carbon atoms that give rise to the signals in the 13C NMR spectrum of each compound.
a. CH3CH2CH2CH2OH ; 13CNMR: 14, 19, 35, and 62 ppm
b. (CH3)2CHCHO ; 13C NMR: 16, 41, and 205 ppm
c. CH2=CHCHOHCH3 ; 13C NMR: 23, 69, 113, and 143 ppm
Question: What effect does increasing the operating frequency of a1HNMR spectrum have on each value: (a) the chemical shift in ;(b) the frequency of an absorption in Hz; (c) the magnitude of a coupling constant J in Hz?
How many NMR signals would you expect for each compound?
a.

b.

c.

Question: Identify the structures of isomers A and B (molecular formula C9H10O ).
Compound A: IR peak at 1742 cm-1 ; 1 H NMR data (ppm) at 2.15 (singlet, 3 H), 3.70 (singlet, 2 H), and 7.20 cm-1(broad singlet, 5 H). Compound B: IR peak at 1688 ; 1 H NMR data (ppm) at 1.22 (triplet, 3 H), 2.98 (quartet, 2 H), and 7.28–7.95 (multiplet, 5 H).
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