Chapter 14: Q16P (page 527)
Question: Sketch the NMR spectrum of\({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{Cl}}\), giving the approximate location of each NMR signal.
Short Answer

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Chapter 14: Q16P (page 527)
Question: Sketch the NMR spectrum of\({\bf{C}}{{\bf{H}}_{\bf{3}}}{\bf{C}}{{\bf{H}}_{\bf{2}}}{\bf{Cl}}\), giving the approximate location of each NMR signal.

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The reaction of (CH3)3 CCHO with (C6H5)3 P=C(CH3)OCH3 , followed by treatment with aqueous acid, afford R . R has strong absorption in its IR spectrum at 1717 cm-1 and three singlets in its -NMR spectrum at 1.02 (9 H), 2.13 (3 H), and 2.33 (2 H) ppm. What is the structure of R? We will learn about this reaction in Chapter 21.
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: Identify the structures of isomers H and I (molecular form C8H11N)
a.

b.

Question: Explain why the 13C NMR spectrum of 3-methylbutan-2-ol shows five signals.
How many NMR signals does each compound give?
a.

b.

c.

d.

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