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2. Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process, aka solvolysis with water. The following are rates of hydrolysis for halogenated derivatives of toluene at 30C in a 50% acetone solution (in water). X,Y,Z represent substituents on the primary carbon in toluene. Rate data taken from JACS 1951, 73, 22-23. Z X = H, Y = CI X = CI, Y = CI X = Br, Y = Br Z = H 0.22 x 10 min¹ 2.21 x 10² min¹¹ 6.85 x 10¹ min¹ Z = CI 2.21 x 10 min¹ 1.105 x 10 min¹ 1.803 x 10 min¹ Z = Br 3.11 x 10³ min¹ 2.122 x 10 min¹ 1.131 x 107 min¹¹ a. Based on what you know about leaving groups, determine whether chloride or bromide is a better leaving group and explain your choice. b. Does the data in the table above support your answer to part a? Explain. C. From the data in the table above, determine whether a carbocation is stabilized by an adjacent chloro group (i.e. a chlorine atom attached to a C+). Justify your choice with drawings (maybe resonance?).

2. Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process, aka solvolysis with water. The following are rates of hydrolysis for halogenated derivatives of toluene at 30C in a 50% acetone solution (in water). X,Y,Z represent substituents on the primary carbon in toluene. Rate data taken from JACS 1951, 73, 22-23. Z X = H, Y = CI X = CI, Y = CI X = Br, Y = Br Z = H 0.22 x 10 min¹ 2.21 x 10² min¹¹ 6.85 x 10¹ min¹ Z = CI 2.21 x 10 min¹ 1.105 x 10 min¹ 1.803 x 10 min¹ Z = Br 3.11 x 10³ min¹ 2.122 x 10 min¹ 1.131 x 107 min¹¹ a. Based on what you know about leaving groups, determine whether chloride or bromide is a better leaving group and explain your choice. b. Does the data in the table above support your answer to part a? Explain. C. From the data in the table above, determine whether a carbocation is stabilized by an adjacent chloro group (i.e. a chlorine atom attached to a C+). Justify your choice with drawings (maybe resonance?).

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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
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2. Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process, aka solvolysis with water. The following are rates of hydrolysis for halogenated derivatives of toluene at 30C in a 50% acetone solution (in water). X,Y,Z represent substituents on the primary carbon in toluene. Rate data taken from JACS 1951, 73, 22-23. X Z X = H, Y = CI X = CI, Y = CI X - Br, Y = Br b. c. Z = H 0.22 x 10 min¹¹ 2.21 x 10 min¹ 6.85 x 10¹ min¹¹ Z = Cl 2.21 x 10 min¹¹ 1.105 x 10 min¹ 1.803 x 10² min¹¹ Z = Br 3.11 x 105 min¹¹ 2.122 x 107 min¹¹ 1.131 x 10 min¹ a. Based on what you know about leaving groups, determine whether chloride or bromide is a better leaving group and explain your choice. Does the data in the table above support your answer to part a? Explain. From the data in the table above, determine whether a carbocation is stabilized by an adjacent chloro group (i.e. a chlorine atom attached to a C+). Justify your choice with drawings (maybe resonance?). d. From the data the table above, determine whether a carbocation is stabilized by an adjacent bromo group (i.e. a bromine atom attached to a C+). Justify your choice with drawings (maybe resonance?). e. Determine whether a carbocation is more greatly stabilized by an adjacent chloro group or an adjacent bromo group. f. For these hydrolysis reactions, determine which factor is more important in predicting the rate of hydrolysis: the stability of the leaving group or the stability of the carbocation?
Transcribed Image Text:2. Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process, aka solvolysis with water. The following are rates of hydrolysis for halogenated derivatives of toluene at 30C in a 50% acetone solution (in water). X,Y,Z represent substituents on the primary carbon in toluene. Rate data taken from JACS 1951, 73, 22-23. X Z X = H, Y = CI X = CI, Y = CI X - Br, Y = Br b. c. Z = H 0.22 x 10 min¹¹ 2.21 x 10 min¹ 6.85 x 10¹ min¹¹ Z = Cl 2.21 x 10 min¹¹ 1.105 x 10 min¹ 1.803 x 10² min¹¹ Z = Br 3.11 x 105 min¹¹ 2.122 x 107 min¹¹ 1.131 x 10 min¹ a. Based on what you know about leaving groups, determine whether chloride or bromide is a better leaving group and explain your choice. Does the data in the table above support your answer to part a? Explain. From the data in the table above, determine whether a carbocation is stabilized by an adjacent chloro group (i.e. a chlorine atom attached to a C+). Justify your choice with drawings (maybe resonance?). d. From the data the table above, determine whether a carbocation is stabilized by an adjacent bromo group (i.e. a bromine atom attached to a C+). Justify your choice with drawings (maybe resonance?). e. Determine whether a carbocation is more greatly stabilized by an adjacent chloro group or an adjacent bromo group. f. For these hydrolysis reactions, determine which factor is more important in predicting the rate of hydrolysis: the stability of the leaving group or the stability of the carbocation?
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