2. Halogenated derivatives of toluene will undergo hydrolysis via an SN1 process, aka solvolysiswith 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. Ratedata taken from JACS 1951, 73, 22-23.XZX = H, Y = CIX = CI, Y = CIX - Br, Y = Brb.c.Z = H0.22 x 10 min¹¹2.21 x 10 min¹6.85 x 10¹ min¹¹Z = Cl2.21 x 10 min¹¹1.105 x 10 min¹1.803 x 10² min¹¹Z = Br3.11 x 105 min¹¹2.122 x 107 min¹¹1.131 x 10 min¹a. Based on what you know about leaving groups, determine whether chloride orbromide 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 byan adjacent chloro group (i.e. a chlorine atom attached to a C+). Justify your choicewith drawings (maybe resonance?).d. From the data the table above, determine whether a carbocation is stabilized byan adjacent bromo group (i.e. a bromine atom attached to a C+). Justify your choicewith drawings (maybe resonance?).e. Determine whether a carbocation is more greatly stabilized by an adjacent chlorogroup or an adjacent bromo group.f. For these hydrolysis reactions, determine which factor is more important inpredicting the rate of hydrolysis: the stability of the leaving group or the stability ofthe carbocation?

SN1 substitution reactions are reactions in which the leaving group is replaced by a nucleophile.…

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?).

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter10: Alcohols

Section: Chapter Questions

Problem 10.52P: Alcohols are important for organic synthesis, especially in situations involving alkenes. The...

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