
Concept explainers
Propose a structure consistent with each set of data.
a. a compound that contains a benzene ring and has a molecular ion at
b. a hydrocarbon that contains only
c. a compound that contains a carbonyl group and gives a molecular ion at
d. a compound that contains

(a)
Interpretation: The structure of a compound that contains a benzene ring and has a molecular ion at
Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element.
Answer to Problem 13.37P
The structure of the compound that contains a benzene ring and has a molecular ion at
Explanation of Solution
The molecular ion peak of a compound is observed at
Possible hydrocarbons are calculated as,
• Divide
Thus, the possible molecular formula is
The molecular ion has odd mass. Thus, the compound may contain
Possible compounds with
• Substitute
Thus, the possible molecular formula is
The molecular mass of
Hence, the structure of a compound that contains a benzene ring and has a molecular ion at
Figure 1
The structure of a compound

(b)
Interpretation: The structure of a hydrocarbon that contains only
Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element.
Answer to Problem 13.37P
The structure of a hydrocarbon
Explanation of Solution
The molecular ion peak of a compound is observed at
Possible hydrocarbons are calculated as,
• Divide
• Replace one carbon by
Thus, the possible molecular formula is
The molecular mass of
Hence, the structure of a hydrocarbon that contains only
Figure 2
The structure of a hydrocarbon

(c)
Interpretation: The structure of a compound that contains a carbonyl group and gives a molecular ion at
Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element.
Answer to Problem 13.37P
The structure of a compound
Explanation of Solution
The molecular ion peak of a compound is observed at
Possible hydrocarbons are calculated as,
• Divide
• Replace one carbon by
The compound that contain
Possible compounds with
• Substitute
Thus, the possible molecular formula is
Hence, the structure of a compound that contains a carbonyl group and gives a molecular ion at
Figure 3
The structure of a compound

(d)
Interpretation: The structure of a compound that contains
Concept introduction: Molecular mass is the sum of the atomic weights of each constituent element multiplied by the number of atoms of that element.
Answer to Problem 13.37P
The structure of a compound
Explanation of Solution
The molecular ion peak of a compound is observed at
Possible hydrocarbons are calculated as,
• Divide
• Replace one carbon by
The given compound contains
Possible compounds with
• Substitute
• Substitute
Thus, the possible molecular formula is
Hence, the structure of a compound that contains
Figure 4
The structure of a compound
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Chapter 13 Solutions
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