tb11 - Chaoter ll-=lleactions of 4lkvl Halides:...

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2. The best leavinggroupin an eliminationreaction. 0 EOTos II eOCCH3 H2O Fe Answer: 8 0 II eOCCH3 H2O Fe e HeF> H2O (CH3)3COe CH3C02 Answer: e ~H2O (CH3)3COe CH3C02 4. The least reactive compound in a SN1 reaction. Cl F Br ~I I CH3CHCH3 PhCHCH3 (CH3hC- I ~CH21 V ~ CH3CH20Tos ~r Chaoter ll-=lleactions of 4lkvl Halides: Nucleoohilic Substitutions and Eliminations Circle your response in each set below. 1. The least reactive compound in an SN2reaction. Answer: ~CH21 V CH3CH2OTos ~r 3. The best nucleophile in a substitution reaction at a primary carbon. 90 Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
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Answer: Cl 8 Br ~I PhCHCH3 (CH3)3C- I 5. The best solvent for an SN2reaction. HMPA CHCl3 H2O CH3CH20H Answer: 8 CHCl3 H2O CH3CH2OH Consider the pair of reactions below to answer the following questions. a. CH3CHzCHzBr -OH, HzO )CH3CHzCHzOH+Br- or b. CH3CHzCHzBr -SH, RSH ) CH3CHzCHzSH + Br- 6. Which reaction would be predicted to be faster? Answer: b 7. Explain your answer to the question above. Answer: -SH is a better nucleophile than -GH because nucleophilicity usually increases in going down a column of the periodic table and sulfur is below oxygen in group 6A. 8. The mechanism for these reactions is: a. SNI b. SN2 c. El d. E2 Answer: b Consider the pair of reactions below to answer the following questions. a. (CH3hC- Cl 70% H2O . 30% CH30H (CH3hC- OH + HCl or b. (CH3)3C- Cl 50% H2O . 50% acetone (CH3hC- OH + HCl 9. Which reaction above is faster? Answer: a Test Items for McMurry's Organic Chemistry, Seventh Edition 91
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Considerthe pair of reactionsbelowto answerthe followingquestions. a. ~lli KI ~] + KBr .. acetone or b. ~Br KI ~I + KBr .. acetone a. b. c. d. 10. Explain your answer to the question above. Answer: The conversion of tert-butyl chloride to tert-butyl alcohol proceeds faster in 70% H2O/30% CH30H than in 50% H2O/50% acetone because SNl reactions are faster in more polar solvents. Acetone (dielectric polarization, P = 20.7) is less polar than CH30H (P = 33.6), and the percentage of H2O is higher in the water/methanol system. 11. The kinetics of these reactions are:
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This note was uploaded on 10/10/2011 for the course CHEMISTRY CHM2046 taught by Professor Johnston during the Spring '11 term at University of South Florida - Tampa.

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tb11 - Chaoter ll-=lleactions of 4lkvl Halides:...

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