Chapter 14: Q17P (page 527)
Question: How many peaks are present in the NMR signal of each labelled proton?
a.

b.

c.

d.

Short Answer
a. 7 peaks
b. 3, 5, 12, and 6 peaks
c. 2 and 6 peaks
d. 4, 4, and 4 peaks
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Chapter 14: Q17P (page 527)
Question: How many peaks are present in the NMR signal of each labelled proton?
a.

b.

c.

d.

a. 7 peaks
b. 3, 5, 12, and 6 peaks
c. 2 and 6 peaks
d. 4, 4, and 4 peaks
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Question:Answer the following questions about each of the hydroxy ketones: 1-hydroxybutan-2-one (A) and 4-hydroxybutan-2-one (B).

a. What is the molecular ion in the mass spectrum?
b. What IR absorptions are present in the functional group region?
c. How many lines are observed in the 13C NMR spectrum?
d. How many signals are observed in the 1H NMR spectrum?
e. Give the splitting observed for each type of proton as well as its approximate chemical shift.
Draw all constitutional isomers of molecular formula C3H6Cl2.
a. How many signals does each isomer exhibit in its 1HNMR spectrum?
b.How many lines does each isomer exhibit in its 13CNMR spectrum?
c. When only the number of signals in both 1Hand 13C NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?
Question: Propose a structure consistent with each set of data.
a. A compound X (molecular formula C6H12O2) gives a strong peak in its IR spectrum at 1740 cm-1. The 1 H NMR spectrum of X shows only two singlets, including one at 3.5 ppm. The 13C NMR spectrum is given below Propose a structure for X.

b. A compound Y (molecular formula C6H10 ) gives four lines in its 13C NMR spectrum (27, 30, 67, and 93 ppm), and the IR spectrum given here. Propose a structure for Y.

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
Rank each group of protons in order of increasing chemical shift.
a.



b.

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