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Compound A (C1,H14) shows prominent peaks in its mass spectrum at m/z 134 and 91. Compound B (also C10H14) shows prominent peaks at m/z 134 and 119. On vigorous oxidation with chromic acid, compound A gave benzoic acid, but compound B was nonreactive. From this information, deduce the structures of both compounds, and then draw the structure of A.

Compound A (C1,H14) shows prominent peaks in its mass spectrum at m/z 134 and 91. Compound B (also C10H14) shows prominent peaks at m/z 134 and 119. On vigorous oxidation with chromic acid, compound A gave benzoic acid, but compound B was nonreactive. From this information, deduce the structures of both compounds, and then draw the structure of A.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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**Description:** Compound A (\(C_{10}H_{14}\)) shows prominent peaks in its mass spectrum at \(m/z\) 134 and 91. Compound B (also \(C_{10}H_{14}\)) shows prominent peaks at \(m/z\) 134 and 119. On vigorous oxidation with chromic acid, compound A gave benzoic acid, but compound B was nonreactive. From this information, deduce the structures of both compounds, and then draw the structure of A. **Guidelines:** - You do not have to consider stereochemistry. - You do not have to explicitly draw H atoms. - Do not include lone pairs in your answer. They will not be considered in the grading.
Transcribed Image Text:**Description:** Compound A (\(C_{10}H_{14}\)) shows prominent peaks in its mass spectrum at \(m/z\) 134 and 91. Compound B (also \(C_{10}H_{14}\)) shows prominent peaks at \(m/z\) 134 and 119. On vigorous oxidation with chromic acid, compound A gave benzoic acid, but compound B was nonreactive. From this information, deduce the structures of both compounds, and then draw the structure of A. **Guidelines:** - You do not have to consider stereochemistry. - You do not have to explicitly draw H atoms. - Do not include lone pairs in your answer. They will not be considered in the grading.
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