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Heating the 4-Methylbenzenesulfonate Ester of the Isomer Shown Below in 2,2,2-Trifluoroethanol

Question 30

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Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C10H18.The major product displays 9 different signals in its 13C NMR spectrum.Two of them occur at relatively low field,about = 120 and 145 ppm,respectively.The 1H NMR spectrum exhibits a multiplet near = 5 ppm (1 H) ; all other signals are upfield of = 3 ppm.Identify the compound. Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C<sub>10</sub>H<sub>18</sub>.The major product displays 9 different signals in its <sup>13</sup>C NMR spectrum.Two of them occur at relatively low field,about <font face= symbol ></font> = 120 and 145 ppm,respectively.The <sup>1</sup>H NMR spectrum exhibits a multiplet near <font face= symbol ></font> = 5 ppm (1 H) ; all other signals are upfield of <font face= symbol ></font> = 3 ppm.Identify the compound. A) <sup> </sup> B) C) D) E)


A)
Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C<sub>10</sub>H<sub>18</sub>.The major product displays 9 different signals in its <sup>13</sup>C NMR spectrum.Two of them occur at relatively low field,about <font face= symbol ></font> = 120 and 145 ppm,respectively.The <sup>1</sup>H NMR spectrum exhibits a multiplet near <font face= symbol ></font> = 5 ppm (1 H) ; all other signals are upfield of <font face= symbol ></font> = 3 ppm.Identify the compound. A) <sup> </sup> B) C) D) E)
B)
Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C<sub>10</sub>H<sub>18</sub>.The major product displays 9 different signals in its <sup>13</sup>C NMR spectrum.Two of them occur at relatively low field,about <font face= symbol ></font> = 120 and 145 ppm,respectively.The <sup>1</sup>H NMR spectrum exhibits a multiplet near <font face= symbol ></font> = 5 ppm (1 H) ; all other signals are upfield of <font face= symbol ></font> = 3 ppm.Identify the compound. A) <sup> </sup> B) C) D) E)
C)
Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C<sub>10</sub>H<sub>18</sub>.The major product displays 9 different signals in its <sup>13</sup>C NMR spectrum.Two of them occur at relatively low field,about <font face= symbol ></font> = 120 and 145 ppm,respectively.The <sup>1</sup>H NMR spectrum exhibits a multiplet near <font face= symbol ></font> = 5 ppm (1 H) ; all other signals are upfield of <font face= symbol ></font> = 3 ppm.Identify the compound. A) <sup> </sup> B) C) D) E)
D)
Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C<sub>10</sub>H<sub>18</sub>.The major product displays 9 different signals in its <sup>13</sup>C NMR spectrum.Two of them occur at relatively low field,about <font face= symbol ></font> = 120 and 145 ppm,respectively.The <sup>1</sup>H NMR spectrum exhibits a multiplet near <font face= symbol ></font> = 5 ppm (1 H) ; all other signals are upfield of <font face= symbol ></font> = 3 ppm.Identify the compound. A) <sup> </sup> B) C) D) E)
E)
Heating the 4-methylbenzenesulfonate ester of the isomer shown below in 2,2,2-trifluoroethanol (a highly ionizing solvent of low nucleophilicity) leads two products with the molecular formula C<sub>10</sub>H<sub>18</sub>.The major product displays 9 different signals in its <sup>13</sup>C NMR spectrum.Two of them occur at relatively low field,about <font face= symbol ></font> = 120 and 145 ppm,respectively.The <sup>1</sup>H NMR spectrum exhibits a multiplet near <font face= symbol ></font> = 5 ppm (1 H) ; all other signals are upfield of <font face= symbol ></font> = 3 ppm.Identify the compound. A) <sup> </sup> B) C) D) E)

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