Nuclear Magnetic Resonance Spectroscopy With Answers Page 2
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CHAPTER 16
Review of Skills
Fill in the blanks and empty boxes below. To verify that your answers are correct, look
in your textbook at the end of Chapter 16. The answers appear in the section entitled
SkillBuilder Review.
16.1 Determining the Relationship between Two Protons in a Compound
FOR EACH OF THE FOLLOWING COMPOUNDS, IDENTIFY THE RELATIONSHIP BETWEEN THE TWO INDICATED PROTONS
(ARE THEY HOMOTOPIC, ENANTIOPTOPIC OR DIASTEREOTOPIC?) AND DETERMINE WHETHER THEY ARE CHEMICALLY
EQUIVALENT.
H
H
H
HO
F F
F Cl
H
H
H
H
H
RELATIONSHIP
CHEMICALLY EQUIVALENT?
1
16.2 Identifying the Number of Expected Signals in a
H NMR Spectrum
FOR EACH OF THE FOLLOWING COMPOUNDS, DETERMINE WHETHER THE TWO INDICATED PROTONS ARE CHEMICALLY
EQUIVALENT.
O
OH
H H
H
H
H
H
H H H H
H
CHEMICALLY EQUIVALENT?
16.3 Predicting Chemical Shifts
FOR EACH OF THE FOLLOWING COMPOUNDS, PREDICT THE EXPECTED CHEMICAL SHIFT OF THE INDICATED PROTONS.
O
HO
O
H
H
H H
O
H H
ppm
ppm
ppm
16.4 Determining the Number of Protons Giving Rise to a Signal
STEP 1 - COMPARE THE
STEP 2 - DIVIDE ALL INTEGRATION
STEP 3 - IDENTIFY THE NUMBER OF PROTONS IN THE COMPOUND
RELATIVE __________________
VALUES BY THE NUMBER FROM
(FROM THE MOLECULAR FORMULA) AND THEN ADJUST THE
VALUES, AND CHOOSE THE
STEP #1, WHICH GIVES THE RATIO
RELATIVE INTEGRATION VALUES SO THAT THE SUM TOTAL
LOWEST NUMBER
OF _____________
EQUALS THE NUMBER OF __________________________________.
16.5 Predicting the Multiplicity of a Signal
IDENTIFY THE EXPECTED MULTIPLICITY FOR EACH SIGNAL IN THE PROTON NMR SPECTRUM
OF THE FOLLOWING COMPOUND.
O
H H
H
CH
3
H
C
3
CH
3
H H
H
C
CH
3
3
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