EBK ORGANIC CHEMISTRY AS A SECOND LANGU
4th Edition
ISBN: 9781119234715
Author: Klein
Publisher: VST
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Chapter 8.5, Problem 8ATS
Interpretation Introduction
Interpretation: The bicycle [3.1.0] hexane ring system is found in natural products like sabinene in black paper. The mechanism of the preparation of this molecule is to be interpreted from compound 1 to compound 3.
Concept Introduction:
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An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C)of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C, and E.
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The bicyclo [3.1.0] hexane ring system, highlighted in compound 3, is found in several natural products, including sabinene, a compound partially responsible for the flavor of ground black pepper. One method for preparing this ring system involves the conversion of compound 1 to compound 2, as shown below. Draw the structure of compound 2 and provide a reasonable mechanism for its formation.
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a. protonate, protonate, nucleophilic attack, nucleophilic attack
b. Nucleophilic attack, protonate, protonate, nucleophilic attack
c. Nucleophilic attack, protonate, nucleophilic attack, protonate
d. Protonate, nucleophilic attack, protonate, nucleophilic attack
Chapter 8 Solutions
EBK ORGANIC CHEMISTRY AS A SECOND LANGU
Ch. 8.3 - Provide a systematic name for each of the...Ch. 8.3 - Prob. 2CCCh. 8.3 - Prob. 3CCCh. 8.3 - Prob. 4CCCh. 8.5 - Prob. 5CCCh. 8.5 - Prob. 6CCCh. 8.5 - Prob. 1LTSCh. 8.5 - Prob. 7PTSCh. 8.5 - Prob. 8ATSCh. 8.5 - Prob. 9CC
Ch. 8.5 - Prob. 2LTSCh. 8.5 - Prob. 10PTSCh. 8.5 - Prob. 11ATSCh. 8.6 - Prob. 12CCCh. 8.6 - Prob. 13CCCh. 8.6 - Prob. 3LTSCh. 8.6 - Prob. 14PTSCh. 8.6 - Prob. 15ATSCh. 8.7 - Predict the product for each reaction, and predict...Ch. 8.7 - Prob. 17CCCh. 8.8 - Prob. 18CCCh. 8.8 - Prob. 19CCCh. 8.8 - Prob. 4LTSCh. 8.8 - Prob. 20PTSCh. 8.8 - Prob. 21ATSCh. 8.9 - Prob. 5LTSCh. 8.9 - Prob. 22PTSCh. 8.9 - Prob. 23ATSCh. 8.10 - Prob. 24CCCh. 8.10 - Prob. 6LTSCh. 8.10 - Prob. 25PTSCh. 8.10 - Prob. 26ATSCh. 8.10 - Prob. 27ATSCh. 8.11 - Prob. 7LTSCh. 8 - Prob. 47PP
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